Перетворення заміщених 3-гідрокси-4-[(2Е)-3-арилпроп-2-еноїл]-1,5-дигідро-2Н-пірол-2-онів під дією I2/ДМСО у похідні 2-арил-5,6-дигідропірано[2,3-с]пірол-4,7-діонів
The effective and simple synthetic preparative procedure for obtaining of various derivatives of 2-aryl-5,6-dihydropyrano[2,3-c]pyrrole-4,7-diones applying the I2/DMSO oxidation of 3-hydroxy-4-[(2E)-3-arylprop-2-enoyl]-1,5-dihydro-2H-pyrrol-2-ones was developed. This protocol was found to be compati...
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V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine
2021
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| author | Vydzhak, Roman N. Panchishin, Svitlana Ya. Prostota, Yaroslav O. Brovarets, Volodymyr S. |
| author_facet | Vydzhak, Roman N. Panchishin, Svitlana Ya. Prostota, Yaroslav O. Brovarets, Volodymyr S. |
| author_institution_txt_mv | [
{
"author": "Roman N. Vydzhak",
"institution": "V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, 1 Murmanska St., Kyiv, 02094, Ukraine"
},
{
"author": "Svitlana Ya. Panchishin",
"institution": "V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, 1 Murmanska St., Kyiv, 02094, Ukraine "
},
{
"author": "Yaroslav O. Prostota",
"institution": "V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, 1 Murmanska St., Kyiv, 02094, Ukraine"
},
{
"author": "Volodymyr S. Brovarets",
"institution": "V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, 1 Murmanska St., Kyiv, 02094, Ukraine"
}
] |
| author_sort | Vydzhak, Roman N. |
| baseUrl_str | https://bioorganica.com.ua/index.php/journal/oai |
| collection | OJS |
| datestamp_date | 2026-07-19T14:56:53Z |
| description | The effective and simple synthetic preparative procedure for obtaining of various derivatives of 2-aryl-5,6-dihydropyrano[2,3-c]pyrrole-4,7-diones applying the I2/DMSO oxidation of 3-hydroxy-4-[(2E)-3-arylprop-2-enoyl]-1,5-dihydro-2H-pyrrol-2-ones was developed. This protocol was found to be compatible with a wide range of substituents and gave the reliable synthetic pathway for the obtaining of target compounds with a wide range of substituents under mild conditions. All obtained substances can be easily isolated and purified by crystallization without application of more complex and labour intensive purification methods |
| doi_str_mv | 10.15407/bioorganica2021.02.003 |
| first_indexed | 2025-07-17T12:19:29Z |
| format | Article |
| fulltext |
ISSN 1814-9758. Ukr. Bioorg. Acta, 2021, Vol. 16, N 2
UDC 547.759+547.816
DOI: https://doi.org/10.15407/bioorganica2021.02.003
3
RESEARCH ARTICLE
Transformation of substituted 3-hydroxy-4-[(2E)-3-arylprop-2-enoyl]-
1,5-dihydro-2H-pyrrol-2-ones by the action of I2/DMSO into derivatives
2-aryl-5,6-dihydropyrano[2,3-c]pyrrole-4,7-diones
Roman N. Vydzhak*, Svitlana Ya. Panchishin, Yaroslav O. Prostota, Volodymyr S. Brovarets
V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, 1 Murmanska St., Kyiv, 02094, Ukraine
Abstract: The effective and simple synthetic preparative procedure for obtaining of various derivatives of 2-aryl-5,6-dihydropyrano[2,3-
c]pyrrole-4,7-diones applying the I2/DMSO oxidation of 3-hydroxy-4-[(2E)-3-arylprop-2-enoyl]-1,5-dihydro-2H-pyrrol-2-ones was
developed. This protocol was found to be compatible with a wide range of substituents and gave the reliable synthetic pathway for the
obtaining of target compounds with a wide range of substituents under mild conditions. All obtained substances can be easily isolated and
purified by crystallization without application of more complex and labour intensive purification methods.
Keywords: multicomponent cyclization; pyrano[2,3-c]pyrrole; I2/DMSO oxidative cyclization.
Introduction
Synthesis of new classes of heterocyclic compounds is
one of the extremely important areas of research in the field
of synthetic medicinal chemistry, since most biologically
active compounds are derivatives of heterocyclic rings
systems [1].
The diversification of heterocyclic compounds using
diversity-oriented synthesis (DOS) has been shown to be an
important tool for the rapid discovery of small biologically
active molecules [2, 3]. Therefore, the development of an
effective strategy leading to molecular skeleton diversity of
synthetic substances is attracting attention in the scientific
communities involved to the search for new potentially
biologically active compounds [4].
Detailed literature analysis of biologically active
compounds containing a pyrone ring showed that they are
mainly consist of derivatives of chromone, flavone, isofla-
Received:
Revised:
Accepted:
Published online:
03.09.2021
23.09.2021
29.10.2021
30.12.2021
Corresponding author. Tel.: +380-44-573-2798;
e-mail: rmvydzhak@gmail.com (R. N. Vydzhak)
ORCID: 0000-0001-7942-169X
Figure 1. Examples of the natural and useful pyrano[2,3-
c]pyrroles and 4,5-dihydropyrrrolo[3,4-c]pyrazoles.
© Vydzhak R. N. et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted
use, distribution, and reproduction in any medium, provided the original author and source are credited.
Ukrainica Bioorganica Acta
www.bi oorgan ica .org .ua
mailto:rmvydzhak@gmail.com
https://orcid.org/0000-0001-5556-9147
ISSN 1814-9758. Ukr. Bioorg. Acta, 2021, Vol. 16, N 2
4
vone and xanthone [5]. This is, mainly, because themain
research focus has been paid on the synthesis of
2,(3)-substituted and 2,3-disubstituted chromones [6-8],
whereas synthetic methodologies for obtaining of pyrone-
condensed rings investigated and developed insufficiently.
Existing reviews summarize synthetic approaches to
pyrano-pyrazole-fused compounds [9], azachomones and
azachromanones [10]. Some methods for the synthesis of
tricyclic heterocyclic systems that include a pyron ring have
also been developed [10, 11].
A unique pyrano[2,3-c]pyrrole bicyclic skeleton,
exhibiting antioxidant activity [12-16] and rarely detected
in nature, was found in Pyranonigrins – secondary
metabolites produced by Aspergillus niger. Pyranonigrin A
is also a potent inhibitor of the Main protease (Mpro) of the
novel SARS-CoV-2 virus [17]. Compounds such as
chromeno[2,3-c]pyrroles were reported to behave as
glucokinase activators [18] and as mimetics of
glycosaminoglycans [19]. Among structurally similar
arylpyrrolone moieties new chemotypes targeting tubulin
for colchicine binding site [20] and anti-cancer therapeutics
[21] have been found (Figure 1).
Pyrano[2,3-c]pyrroles are practically unexplored and
undescribed class of fused heterocyclic compounds. They
were mentioned only in the one paper that describes
the synthesis of a compound containing a
6,7-dihydropyrano[2,3-c]pyrrole-4,5-dione system [22], and
in the another, referred to the obtaining of
5,6-dihydropyrano[2,3-c]pyrrole-4,7-dione [23, 24].
Aiming at accessing diverse molecular skeletons of
pyrano[2,3-c]pyrrole, we performed rapid and efficient
pathway for construction of target libraries of drug-like
compounds – 2-aryl-5,6-dihydropyrano[2,3-c]pyrrole-4,7-
diones from relatively simple and commercially available
starting reagents via I2/DMSO oxidative cyclization.
Results and Discussion
The only two representatives of 2-aryl-5,6-dihydro-
pyrano[2,3-c]pyrrole-4,7-diones deriva-tives were obtained
earlier [23] by oxidation of N-thiazolyl 3-hydroxy-4-[(2E)-
3-phenylprop-2-enoyl]-1,5-dihydro-2H-pyrrol-2-one deriva-
tives. The synthesis of target 3-hydroxy-1,5-dihydro-2H-
pyrrol-2-one (4) is presented on Scheme 1.
3-Hydroxy-1-alkyl-1,5-dihydro-2H-pyrrol-2-one (4а) and
3-hydroxy-1-hetaryl-1,5-dihydro-2H-pyrrol-2-one (4с) were
obtained starting from relatively simple and commercially
available reagents via one-pot multicomponent
heterocyclization [23, 25].
It should be noted that one-pot multicomponent reactions
(MCRs) are one of the most efficient tools in modern
preparative organic chemistry for the preparation of widely
functionalized synthetic organic compounds [26].
Compounds 4a were prepared from aldehydes, aliphatic
amines and esters 1 in methanol, while derivatives of 4c
from aldehydes, heterocyclic amines and esters 1 in glacial
acetic acid. 3-Hydroxy-1-aryl-1,5-dihydro-2H-pyrrol-2-one
(4b) were synthesized by heating esters 1 and Schiff bases
(previously obtained from aldehydes and aromatic amines)
also in glacial acetic acid as solvent. The representative
substrates – methyl 2,4-dioxo-6-arylhex-5-enoates (1{1-2})
[27], aldehydes (2{1-7}), and amines (3{1-7}) are listed on
Figure 2.
The structure and composition of compounds 4 were
confirmed by 1H NMR spectroscopy and elemental
analysis. The signals of all observed in the 1H NMR spectra
protons were appeared in usual spectral regions which
unambiguously corresponds to the structure of the
synthesized substances. The signal of 5-H of compounds 4
was found as a singlet at 5.20-6.25 ppm range. The signal of
the NCH3 group of compounds 4a appeared as a singlet at
2.65-2.75 ppm. The signals of the NCH2 group of
O
O1
4a
O
N Ar
HO
O
R2
4b 4c
R2
O
R2
O
R2 N
Ar
AlkNH2 (3a ) HetNH2 (3c )
(2) (2)
(2+3b)
OMe
OH
R1
R1
H H
O
N Alk
HO
O
R2
R1
O
N Het
HO
O
R2
R1
Scheme 1. Synthesis of 3-hydroxy-4-[(2E)-arylprop-2-enoyl]-1,5-dihydro-2H-pyrrol-2-one derivatives 4a-c.
R. N. Vydzhak., S. Ya. Panchishin et al.
5
Figure 2. Scope of methyl 2,4-dioxo-6-arylhex-5-enoates 1{1-2}, aldehydes 2{1-7} and amines 3 {1-7}.
compounds 4{1-1-2} and 4{1-2-2} were found as doublets
of triplets. The CH= signals of the propenyl fragment are
usually overlapped with the signals of aromatic protons, but
in some cases they were manifested separately as doublets
(JHH = 14.8 Hz), which predominantly indicated trans-
configuration of this fragment. In the 1H NMR spectrum of
compounds 4 measured in DMSO-d6, the signals of
hydroxyl group proton were not detected at all. Molecular
ion peaks [M+H]+ and [M-H]- are usually detected in
LC/MS spectra of the compounds 4.
Scheme 2. Synthesis of 2-aryl-5,6-dihydropyrano[2,3-c]pyrrole-
4,7-dione derivatives.
The synthesis of 5,6-dihydropyrano[2,3-c]pyrrole-4,7-
dione (5) is shown on Scheme 2. Derivatives of final
compounds 5 were obtained by boiling of compounds 4 in
DMSO in the presence of a catalytic amount of iodine with
moderate yields. This is a key stage in the strategy of
pyrano[2,3-c]pyrrole synthesis and these are rather harsh
reaction conditions. It is obvious, when the substituents in
the pyrrole skeleton are stable enough under these
conditions, there should be a transformation of 3-hydroxy-
1,5-dihydro-2H-pyrrol-2-ones (4) into 5,6-dihydropyra-
no[2,3-c]pyrrole-4,7-diones (5). It was found that presence
of a halogen atom or other non-oxidizing group in the
aromatic aldehyde as a substituent didn’t significantly affect
on the yield of the target products. Therefore, we obtained
pyrrole derivatives 5 from 4-methoxybenzaldehyde 4{1-3-
1} and 3,4-dimethoxybenzaldehyde 4{1-4-1} and showed
that they were able to convert into pyrone 5 derivatives
without any significant tarring. Thus, pyrano[2,3-c]pyrrole-
4,7-diones with pyridyl 5{1-7-1} and thietyl 5{1-6-1}
substituents were obtained, although the yield of product
5{1-6-1} is quite low, mainly due to the partial formation of
resinous products from the reaction mixture.
The conversion of derivative 4{1-5-1} (containing a
furyl substituent) into the target product 5 was failed,
resulted only in the strong tarring/decomposition of the
reaction mixture. It should be noted that replacement of
alkyl substituents on the nitrogen atom does not
significantly affect the proceeding of this reaction, the
change of heterocyclic substituents, similarly, also have no
impact on the course of cyclization, while the methyl
groups of dimethylthiazole and methylthiadiazole fragments
do not oxidize at all. The target derivatives 5 with a
fragment of aniline 5{1-1-3}, and more prone to oxidation
residue of 4-methoxyaniline 5{1-1-4}, were also obtained.
The introduction of the methoxy group to the aromatic ring
of ether 1 did not affect significantly on the yields of
compounds 4 and their following conversion into the target
derivatives 5. Considering all results mentioned above, it
ISSN 1814-9758. Ukr. Bioorg. Acta, 2021, Vol. 16, N 2
6
was concluded that it is possible to apply a large set of
aromatic amines in these synthetic transformations.
The structure and composition of compounds 5 were
confirmed by 1H NMR spectroscopy and elemental
analysis. The signals of all observed in the 1H NMR spectra
protons appear in usual spectral regions which
unambiguously corresponds to the structure of the
synthesized substances. The signal of 3-H of compounds 5
was found as a singlet in the range 7.00-7.20 ppm, and its
position is weakly dependent on substituents. The signal of
5-H of compounds 5 was found as a singlet in the range
6.30-6.50 ppm in the case of N-aryl and N-hetaryl
substituted 5,6-dihydropyrano[2,3-c]pyrrole-4,7-diones, and
as a singlet in the range 6.95-7.30 ppm in the case of
N-alkyl derivatives 5. The IR spectra (KBr) contain tree
strong absorption band in the region 1600-1750 cm-1: 1620-
1640, 1660-1680, 1695-1730 cm-1. No absorption was
observed in the region 3150-3600 cm-1, indicated that the
cyclization involved the hydroxyl group in 4. Molecular ion
peak [M+H]+ are usually detected in LC/MS spectra in the
case of N-aryl and N-hetaryl substituted compounds 5 and
ion peak [M+16+H]+.
Conclusions
It was shown that 3-hydroxy-4-[(2E)-3-arylprop-2-
enoyl]-1,5-dihydro-2H-pyrrol-2-ones derivatives can be
used as starting materials to obtain various 2-aryl-5,6-
dihydropyrano[2,3-c]pyrrole-4,7-diones by I2/DMSO
oxidative cyclization. Thus, several pyrrole derivatives were
obtained using a one-pot version of a multicomponent
reaction based on the interaction of methyl 2,4-dioxo-6-
arylhex-5-enoates, aldehydes and amines. It was established
that this synthetic protocol is compatible with a wide range
of substituents and may apply as the pathway to the
synthesis of the target pyrano[2,3-c]pyrroles. This synthetic
methodology may be useful for obtaining of some fairly
studied multi-rings heterocyclic compounds. Obtained
library of 2-aryl-5,6-dihydropyrano[2,3-c]pyrrole-4,7-
diones (18 compounds) can be easily expanded and
represents a real opportunity to discover novel drugs
candidates.
Experimental section
All used solvents were of analytical grade. The 1H NMR
spectra were recorded at 298 K on a Varian GEMINI 2000
spectrometer (at 400 MHz) in solutions of DMSO-d6 (TMS
as internal reference). Chemical shifts (δ) are reported in
ppm and coupling constants (J) in Hz. Chemical ionization
at atmospheric pressure mass spectra (APCI) were
measured with an Agilent 1200 LC\MSD SL system
equipped with DAD/ELSD/LSMS-6120 diode matrix and
mass-selective detector, scan range m/z 80-1000. IR spectra
were obtained on a Vertex-70 FTIR spectrometer using KBr
pellets. Wavenumbers (max) are reported in cm-1. Melting
points were determined in a Fischer-Johns melting point
apparatus and are uncorrected. Elemental analysis was
carried out in the Analytical Laboratory of the Institute of
Bioorganic and Petrochemistry of the National Academy of
Sciences of Ukraine by manual methods: the carbon and
hydrogen contents were determined using the Pregl
gravimetric method, nitrogen was determined using the
Duma’s gasometrical micromethod and sulfur was
determined by the Scheininger titrimetric method.
General procedure for the synthesis of 3-hydroxy-1-
alkyl-1,5-dihydro-2H-pyrrol-2-one 4a.
To a solution of 10 mmol of the corresponding aldehyde
2 in 10 ml of methanol 10 mmol of aliphatic amine 3 in
10 ml of methanol was added. The mixture was kept for
30 °C min at 40 °C, cooled to 20 °C, then 10 mmol of the
corresponding compound 1 was added and the mixture was
continiuosly heated for 1 h at 50 °C. The precipitate formed
at cooling to 0-5 °C was filtered off, washed with methanol
(10 mL), ethyl acetate (10 mL) and crystallized with ethyl
acetate to afford 4a as colorless solids.
3-Hydroxy-1-methyl-5-phenyl-4-[(2E)-3-phenylprop-2-
enoyl]-1,5-dihydro-2H-pyrrol-2-one (4{1-1-1}).
Yield 55%; mp 194-195 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.56-7.67 (m, 3H, HC=, Ar), 7.39-7.49 (m,
4H, HC=, Ar), 7.21-7.37 (m, 5H, Ar), 5.29 (s, 1H, 5H), 2.67
(s, 3H, NCH3). IR (KBr) ν 3064 (OH), 1693 (C=O), 1646
(C=O), 1595 (C=C). MS (APCI) m/z 320.1 [M+H]+, 318.0
[M-H]-. Anal. Calcd. for C20H17NO3: C, 75.22; H, 5.37; N,
4.29. Found: C, 75.11; H, 5.29; N, 4.40.
5-(4-Chlorophenyl)-3-hydroxy-1-methyl-4-[(2E)-3-phe-
nylprop-2-enoyl]-1,5-dihydro-2H-pyrrol-2-one (4{1-2-1}).
Yield 63%; mp 232-233 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.58-7.68 (m, 3H, HC=, Ar), 7.41-7.50 (m,
4H, HC=, Ar), 7.40 (d, J 8.4 Hz, 2H, Ar), 7.27 (d, J 8.4 Hz,
2H, Ar), 5.31 (s, 1H, 5-H), 2.68 (s, 3H, NCH3). IR (KBr)
ν 3057 (OH), 1691 (C=O), 1650 (C=O), 1593 (C=C).
MS (APCI) m/z 357.2 ([M(37Cl)+H]+, 30), 354.2
([M(35Cl)+H]+, 100), 354.2 ([M(37Cl)-H]-, 30), 352.2
([M(35Cl)-H]-, 100). Anal. Calcd. for C20H16ClNO3: C,
67.90; H, 4.56; N, 3.96. Found: C, 67.75; H, 4.61; N, 4.05.
3-Hydroxy-5-(4-methoxyphenyl)-1-methyl-4-[(2E)-3-
phenylprop-2-enoyl]-1,5-dihydro-2H-pyrrol-2-one (4{1-3-
1}).
Yield 48%; mp 216-217 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.55-7.68 (m, 3H, HC=, Ar), 7.37-7.52 (m,
4H, HC=, Ar), 7.15 (d, 2H, J 8.7 Hz, Ar), 6.89 (d, 2H, J 8.7
Hz, Ar), 5.25 (s, 1H, 5-H), 3.73 (s, 3H, OCH3), 2.67(s, 3H,
NCH3). IR (KBr) ν 3096 (OH), 1688 (C=O), 1658 (C=O),
1591 (C=C). MS (APCI) m/z 350.2 [M+H]+, 348.2 [M-H]-.
Anal. Calcd. for C21H19NO4: C, 72.19; H, 5.48; N, 4.01.
Found: C, 72.14; 5.54; N, 4.05.
5-(3,4-Dimethoxyphenyl)-3-hydroxy-1-methyl-4-[(2E)-3-
phenylprop-2-enoyl]-1,5-dihydro-2H-pyrrol-2-one (4{1-4-
1}).
Yield 67%; mp 195-196 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.55-7.68 (m, 3H, HC=, Ar), 7.39-7.53 (m,
4H, HC=, Ar), 6.91 (d, 1H, J 8.2 Hz, Ar), 6.72-6.85 (m, 2H,
R. N. Vydzhak., S. Ya. Panchishin et al.
7
Ar), 5.25 (s, 1H, 5-H), 3.73 (s, 3H, OCH3), 3.71 (s, 3H,
OCH3), 2.69 (s, 3H, NCH3). IR (KBr) ν 3082 (OH), 1689
(C=O), 1643 (C=O), 1586 (C=C). MS (APCI) m/z 380.0
[M+H]+, 378.1 [M-H]-. Anal. Calcd. for C22H21NO5:
C, 69.65; H, 5.58; N, 3.69. Found: C, 69.74; H, 5.49; N,
3.76.
5-(2-Furyl)-3-hydroxy-1-methyl-4-[(2E)-3-phenylprop-2-
enoyl]-1,5-dihydro-2H-pyrrol-2-one (4{1-5-1}).
Yield 45%; mp 175-177 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.60-7.67 (m, 3H, HC=, Ar), 7.56 (d, 1H, J 1.9
Hz, Ar), 7.52 (d, 1H, J 15.8 Hz, HC=), 7.42-7.48 (m, 3H,
Ar), 6.54 (d, 1H, J 3.3 Hz, Ar), 6.43 (dd, 1H, J 3.3, 1.9 Hz,
Ar), 5.47 (s, 1H, 5-H), 2.75 (s, 3H, NCH3). IR (KBr) ν 3073
(OH), 1699 (C=O), 1646 (C=O), 1585 (C=C). MS (APCI)
m/z 310.1 [M+H]+, 308.0 [M-H]-. Anal. Calcd. for
C18H15NO4: C, 69.89; H, 4.89; N, 4,53. Found: C, 69.75; H,
4.82; N, 4.62.
3-Hydroxy-1-methyl-4-[(2E)-3-phenylprop-2-enoyl]-5-
(2-thienyl)-1,5-dihydro-2H-pyrrol-2-one (4{1-6-1}).
Yield 56%; mp 179-180 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.58-7.68 (m, 3H, HC=, Ar), 7.51 (d, 1H,
J 15.9 Hz, HC=), 7.41-7.48 (m, 4H, Ar), 7.26 (d, 1H, J 3.5
Hz, Ar), 7.00 (dd, 1H, J 5.1, 3.5 Hz, Ar), 5.68 (s, 1H, 5-H),
2.75 (s, 3H, NCH3). IR (KBr) ν 3080 (OH), 1700 (C=O),
1644 (C=O), 1585 (C=C). MS (APCI) m/z 326.2 [M+H]+,
324.1 [M-H]-. Anal. Calcd. for C18H15NO3S:
C, 66.44; H, 4.65; N, 4.30. Found: C, 66.31; H, 4.72; N,
4.41.
3-Hydroxy-1-methyl-4-[(2E)-3-phenylprop-2-enoyl]-5-
pyridin-3-yl-1,5-dihydro-2H-pyrrol-2-one (4{1-7-1}).
Yield 65%; mp 230-232 °C. 1H NMR (400 MHz,
DMSO-d6) δ 8.56-8.60 (m, 1H, Ar), 8.51 (dd, 1H, J 4.8, 1.6
Hz, Ar), 7.67 (d, 1H, J 15.8 Hz, HC=), 7.56-7.62 (m, 3H,
Ar), 7.40-7.49 (m, 4H, HC=, Ar), 7.37 (dd, 1H, J 7.9, 4.8
Hz, Ar), 5.25 (s, 1H, 5-H), 2.71(s, 3H, NCH3). IR (KBr) ν
3101 (OH), 1701 (C=O), 1639 (C=O), 1580 (C=C). MS
(APCI) m/z 321.1 [M+H]+, 319.0 [M-H]-. Anal. Calcd. for
C19H6N2O3: C, 71.24; H, 5.03; N, 8.74. Found: C, 71.35;
H, 5.11; N, 8.69.
1-Ethyl-3-hydroxy-5-phenyl-4-[(2E)-3-phenylprop-2-en-
oyl]-1,5-dihydro-2H-pyrrol-2-one (4{1-1-2}).
Yield 45%; mp 214-215 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.56-7.68 (m, 3H, HC=, Ar), 7.39-7.52
(m, 4H, HC=, Ar), 7.23-7.38 (m, 5H, Ar), 5.40 (s, 1H,
5-H), 3.54 (dt, 1H, J 14.5, 7.2 Hz, NCH2), 2.68 (dt, 1H,
J 14.5, 7.2 Hz, NCH2), 0.96 (t, 3H, J 7.2 Hz, CH3).
IR (KBr) ν 3105 (OH), 1680 (C=O), 1650 (C=O), 1595
(C=C). MS (APCI) m/z 334.0 [M+H]+, 332.0 [M-H]-. Anal.
Calcd. for C21H19NO3: C, 75.66; H, 5.74; N, 4.20. Found: C,
75.51; H, 5.65; N, 4.29.
5-(4-Chlorophenyl)-1-ethyl-3-hydroxy-4-[(2E)-3-phenyl-
prop-2-enoyl]-1,5-dihydro-2H-pyrrol-2-one (4{1-2-2}).
Yield 52%; mp 220-222 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.63 (d, 1H, J 15.8 Hz, HC=), 7.51-7.59 (m,
2H, Ar), 7.33-7.47 (m, 4H, HC=, Ar), 7.21-7.32 (m, 4H,
Ar), 5.31 (s, 1H, 5-H), 3.64 (dt, 1H, J 14.1, 7.2 Hz, NCH2),
2.73 (dt, 1H, J 14.1, 7.2 Hz, NCH2), 1.06 (t, 3H, J 7.2 Hz,
CH3). IR (KBr) ν 3078 (OH), 1686 (C=O), 1643 (C=O),
1593 (C=C). Anal. Calcd. for C21H18ClNO3: C, 68.57; H,
4.93; N, 3.81. Found: C, 68.45; H, 5.01; N, 3.90.
3-Hydroxy-4-[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]-
1-methyl-5-phenyl-1,5-dihydro-2H-pyrrol-2-one (4{2-1-1}).
Yield 60%; mp 191-193 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.48-7.58 (m, 3H, HC=, Ar), 7.40 (d, 1H,
J 15.8 Hz, HC=), 7.19-7.36 (m, 5H, Ar), 6.99 (d, 2H,
J 8.8 Hz, Ar), 5.26 (s, 1H, 5-H), 3.79 (s, 3H, OCH3), 2.79
(s, 3H, NCH3). IR (KBr) ν 3288 (OH), 1703 (C=O), 1645
(C=O), 1583 (C=C). MS (APCI) m/z 350.2 [M+H]+, 348.1
[M-H]-. Anal. Calcd. for C21H19NO4: C, 72.19; H, 5.48; N,
4.01. Found: 72.07; H, 5.57; N, 4.13.
5-(4-Chlorophenyl)-3-hydroxy-4-[(2E)-3-(4-methoxy-
phenyl)prop-2-enoyl]-1-methyl-1,5-dihydro-2H-pyrrol-2-
one (4{2-2-1}).
Yield 65%; mp 221-223 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.55 (d, 2H, J 8.4 Hz, Ar), 7.41-7.52 (m, 2H,
2HC=), 7.39 (d, 2H, J 8.2 Hz, Ar), 7.27 (d, 2H, J 8.2 Hz,
Ar), 6.99 (d, 2H, J 8.4 Hz, Ar), 5.30 (s, 1H, 5-H), 3.79 (s,
3H, OCH3), 2.68 (s, 3H, NCH3). IR (KBr) ν 3098 (OH),
1693 (C=O), 1639 (C=O), 1584 (C=C). MS (APCI) m/z
([M(37Cl)+H]+; 30), 384.2 ([M(35Cl)+H]+, 100), 384.2
([M(37Cl)-H]-, 30), 382.2 ([M(35Cl)-H]-, 100). Anal. Calcd.
for C21H18ClNO4: C, 65.71; H, 4.73; N, 3.65. Found:
C, 65.84; H, 4.69; N, 3.73.
3-Hydroxy-5-(4-methoxyphenyl)-4-[(2E)-3-(4-methoxy-
phenyl)prop-2-enoyl]-1-methyl-1,5-dihydro-2H-pyrrol-2-
one (4{2-3-1}).
Yield 62%; mp 185-187 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.56 (d, 2H, J 8.7 Hz, Ar), 7.34-7.49 (m, 2H,
2HC=), 7.15 (d, 2H, J 8.8 Hz, Ar), 6.99 (d, 2H, J 8.8 Hz,
Ar), 6.89 (d, 2H, J 8.7 Hz, Ar), 5.24 (s, 1H, 5-H), 3.79
(s, 3H, OCH3), 3.73 (s, 3H, OCH3), 2.66 (s, 3H, NCH3).
IR (KBr) ν 3200 (OH), 1695 (C=O), 1662 (C=O), 1585
(C=C). MS (APCI) m/z 380.0 [M+H]+, 378.1 [M-H]-. Anal.
Calcd. for C22H21NO5: C, 69.65; H, 5.58; N, 3.69. Found: C,
69.78; H, 5.51; N, 3.81.
General Procedure for the Synthesis of 3-hydroxy-1-
aryl-1,5-dihydro-2H-pyrrol-2-one 4b
A mixture of 10 mmol of compound 1 and 10 mmol of
N-benylideneaniline (previously obtained from aldehydes
and aromatic amines) in 10 mL of glacial acetic acid was
heated to reflux for 30 min. After cooling to ambient
temperature the formed precipitate was filtered off, washed
with acetic acid (5 mL), ethanol (10 mL) and crystallized
with DMF-ethanol mixture to afford 4b as light yellow
solids.
3-Hydroxy-1,5-diphenyl-4-[(2E)-3-phenylprop-2-enoyl]-
1,5-dihydro-2H-pyrrol-2-one (4{1-1-3}).
Yield 46%; mp 224-226 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.68 (d, 1H, J 15.9 Hz, HC=), 7.59-7.65 (m,
ISSN 1814-9758. Ukr. Bioorg. Acta, 2021, Vol. 16, N 2
8
4H, Ar), 7.50 (d, 1H, J 15.9 Hz, HC=), 7.40-7.47 (m, 3H,
Ar), 7.26-7.35 (m, 4H, Ar), 7.16-7.22 (m, 2H, Ar), 7.06-
7.14 (m, 2H, Ar), 6.22 (s, 1H, 5-H). IR (KBr) ν 3160 (OH),
1684 (C=O), 1648 (C=O), 1604 (C=C). MS (APCI) m/z
382.2 [M+H]+, 380.0 [M-H]-. Anal. Calcd. for C25H19NO3:
C, 78.72; H, 5.02. Found: C,78.93; H, 5.07.
3-Hydroxy-1-(4-methoxyphenyl)-5-phenyl-4-[(2E)-3-
phenylprop-2-enoyl]-1,5-dihydro-2H-pyrrol-2-one (4{1-1-
4}).
Yield 53%; mp 205-207 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.68 (d, 1H, J 15.9 Hz, HC=), 7.61-7.65 (m,
2H, Ar), 7.40-7.53 (m, 6H, HC=, Ar), 7.26-7.31 (m, 2H,
Ar), 7.09-7.24 (m, 3H, Ar), 6.86 (d, 2H, J 9.0 Hz, Ar), 6.14
(s, 1H, 5-H), 3.68 (s, 3H, OCH3). IR (KBr) ν 3180 (OH),
1683 (C=O), 1650 (C=O), 1595 (C=C). MS (APCI) m/z
412.2 [M+H]+, 410.2 [M-H]-. Anal. Calcd. for C26H21NO4:
C, 75.90; H, 5.14. Found: C, 75.78; H, 5.09.
3-Hydroxy-4-[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]-
1,5-diphenyl-1,5-dihydro-2H-pyrrol-2-one (4{2-1-3}).
Yield 57%; mp 218-220 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.56-7.65 (m, 4H, Ar), 7.54 (d, 1H, J 15.8 Hz,
HC=), 7.46 (d, 1H, J 15.8 Hz, HC=), 7.26-7.34 (m, 4H, Ar),
7.17-7.23 (m, 2H, Ar), 7.07-7.15 (m, 2H, Ar), 7.01 (d, 2H,
J 8.4 Hz, Ar), 6.20 (s, 1H, 5-H), 3.80 (s, 3H, OCH3).
IR (KBr) ν 3190 (OH), 1691 (C=O), 1658 (C=O), 1585
(C=C). MS (APCI) m/z 412.1 [M+H]+, 410.0 [M-H]-. Anal.
Calcd. for C26H21NO4: C, 75.90; H, 5.14. Found: C, 76.05;
H, 5.19.
General Procedure for the Synthesis of 3-hydroxy-1-
hetaryl-1,5-dihydro-2H-pyrrol-2-one 4c.
A mixture of 10 mmol of compound 1, 10 mmol of
aromatic aldehyde 2 and 10 mmol of the corresponding
heterocyclic amine 3 in 15 ml of glacial acetic acid was
heated to reflux for 20 min. After cooling to ambient
temperature the formed precipitate was filtered off, washed
with acetic acid (5 mL), ethanol (10 mL) and crystallized
with DMF-ethanol mixture to afford 4c as light yellow
solids.
3-Hydroxy-5-phenyl-4-[(2E)-3-phenylprop-2-enoyl]-1-
(1,3-thiazol-2-yl)-1,5-dihydro-2H-pyrrol-2-one (4{1-1-5}).
Yield 42%; mp 246-247 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.60-7.71 (m, 3H, HC=, Ar), 7.50 (d, 1H,
J 15.8 Hz, HC=), 7.42-7.47 (m, 4H, Ar), 7.30-7.38 (m, 3H,
Ar), 7.18-7.28 (m, 3H, Ar), 6.12 (s, 1H, 5-H). IR (KBr)
ν 3200 (OH), 1690 (C=O), 1650 (C=O), 1600 (C=C). MS
(APCI) m/z 389.2 [M+H]+, 387.0 [M-H]-. Anal. Calcd. for
C22H16N2O3S: C, 68.03; H, 4.15; N, 7.21; S, 8.25. Found: C,
67.88; H, 4.19; N, 7.34; S, 8.39.
5-(4-Chlorophenyl)-3-hydroxy-4-[(2E)-3-phenylprop-2-
enoyl]-1-(1,3-thiazol-2-yl)-1,5-dihydro-2H-pyrrol-2-one
(4{1-2-5}).
Yield 45%; mp 242-243 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.68 (d, 1H, J 15.8 Hz, HC=), 7.58-7.63 (m,
2H, Ar), 7.49 (d, 1H, J 15.8 Hz, HC=), 7.35-7.44 (m, 6H,
Ar), 7.20-7.29 (m, 3H, Ar), 6.07 (s, 1H, 5-H). IR (KBr)
ν 3200 (OH), 1690 (C=O), 1652 (C=O), 1595 (C=C). Anal.
Calcd. for C22H15ClN2O3S: C, 62.48; H, 3.58; N, 6.62; S,
7.58. Found: C, 62.35; H, 3.49; N, 6.71; S, 7.74.
1-(4,5-Dimethyl-1,3-thiazol-2-yl)-3-hydroxy-5-phenyl-4-
[(2E)-3-phenylprop-2-enoyl]-1,5-dihydro-2H-pyrrol-2-one
(4{1-1-6}).
Yield 47%; mp 252-254 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.59-7.70 (m, 3H, HC=, Ar), 7.49 (d, 1H,
J 15.9 Hz, HC=), 7.40-7.45 (m, 3H, Ar), 7.31-7.35 (m, 2H,
Ar), 7.16-7.29 (m, 3H, Ar), 6.06 (s, 1H, 5-H), 2.21 (s, 3H,
CH3), 2.04 (s, 3H, CH3). IR (KBr) ν 3170 (OH), 1710
(C=O), 1642 (C=O), 1585 (C=C). MS (APCI) m/z 417.1
[M+H]+, 415.0 [M-H]-. Anal. Calcd. for C24H20N2O3S: C,
69.21; H, 4.84; N, 6.73; S, 7.70. Found: C, 69.08; H, 4.89;
N, 6.85; S, 7.89.
3-Hydroxy-1-(5-methyl-1,3,4-thiadiazol-2-yl)-5-phenyl-
4-[(2E)-3-phenylprop-2-enoyl]-1,5-dihydro-2H-pyrrol-2-
one (4{1-1-7}).
Yield 44%; mp 253-255 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.69 (d, 1H, J 15.9 Hz, HC=), 7.62-7.65 (m,
2H, Ar), 7.51 (d, 1H, J 15.9 Hz, HC=), 7.41-7.46 (m, 3H,
Ar), 7.36-7.41 (m, 2H, Ar), 7.18-7.30 (m, 3H, Ar), 6.12 (s,
1H, 5-H), 2.59 (s, 3H, CH3). IR (KBr) ν 3200 (OH), 1696
(C=O), 1646 (C=O), 1596 (C=C). MS (APCI) m/z 404.0
[M+H]+, 402.0 [M-H]-. Anal. Calcd. for C22H17N3O3S:
C, 65.49; H, 4.25; N, 10.41; S, 7.95. Found: C, 65.38; H,
4.19; N, 10.53; S, 8.14.
General Procedure for the Synthesis of 5,6-
dihydropyrano[2,3-c]pyrrole-4,7-dione 5.
A catalytic amount of iodine was added to a solution of
3 mmol of compound 4 in 15 ml DMSO, and the mixture
was heated to reflux for 1 h. The reaction mixture was
cooled to ambient temperature and then chilled to 0 °C,
diluted with 50 mL of water, the formed precipitate was
filtered off, washed with a 5% water solution of sodium
thiosulfate (to remove traces of iodine), water, dried at air
and crystallized from DMF-ethanol to afford 5.
6-Methyl-2,5-diphenyl-5,6-dihydropyrano[2,3-c]pyrrole-
4,7-dione (5{1-1-1}).
Yield 56%; mp 246-248 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.95-8.02 (m, 2H, Ar), 7.54-7.61 (m, 3H, Ar),
7.43-7.48 (m, 2H, Ar), 7.31-7.39 (m, 3H, Ar), 7.10 (s, 1H,
3-H), 7.06 (s, 1H, 5-H), 2.66 (s, 3H, NCH3). IR (KBr)
ν 1701 (C=O), 1656 (C=O), 1627 (C=C). MS (APCI) m/z
318.2 [M+H]+. Anal. Calcd. for C20H15NO3: C, 75.70;
H, 4.75; N, 4.41. Found: C, 75.54; H, 4.69; N, 4.52.
5-(4-Chlorophenyl)-6-methyl-2-phenyl-5,6-dihydropyra-
no[2,3-c]pyrrole-4,7-dione (5{1-2-1}).
Yield 58%; mp 248-250 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.95-8.01 (m, 2H, Ar), 7.56-7.63 (m, 3H, Ar),
7.43 (d, 2H, J 8.5 Hz, Ar), 7.27 (d, 2H, J 8.5 Hz, Ar), 7.27
(s, 1H, 5-H), 7.12 (s, 1H, 3-H), 2.63 (s, 3H, NCH3).
IR (KBr) ν 1702 (C=O), 1656 (C=O), 1627 (C=C). MS
R. N. Vydzhak., S. Ya. Panchishin et al.
9
(APCI) m/z 354.2 ([M(37Cl)+H]+; 30), 352.2 ([M(35Cl)+H]+,
100). Anal. Calcd. for C20H15ClNO3: C, 68.29; H, 4.01; N,
3.98. Found: C, 68.19; H, 4.09; N, 4.07.
5-(4-Methoxyphenyl)-6-methyl-2-phenyl-5,6-dihydro-
pyrano[2,3-c]pyrrole-4,7-dione (5{1-3-1}).
Yield 48%; mp 247-248 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.96-8.02 (m, 2H, Ar), 7.56-7.63 (m, 3H, Ar),
7.37 (d, 2H, J 8.4 Hz, Ar), 7.10 (s, 1H, 3-H), 7.06 (s, 1H,
5-H), 6.91 (d, 2H, J 8.4 Hz, Ar), 3.74 (s, 3H, OCH3), 2.64
(s, 3H, NCH3). IR (KBr) ν 1703 (C=O), 1662 (C=O), 1629
(C=C). MS (APCI) m/z 348.0 [M+H]+. Anal. Calcd. for
C21H17NO4: C, 72.61; H, 4.93; N, 4.03. Found: C, 72.75; H,
4.90; N, 4.14.
5-(3,4-Dimethoxyphenyl)-6-methyl-2-phenyl-5,6-dihyd-
ropyrano[2,3-c]pyrrole-4,7-dione (5{1-4-1}).
Yield 53%; mp 196-197 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.96-8.03 (m, 2H, Ar), 7.54-7.62 (m, 3H, Ar),
7.11 (s, 1H, 3-H), 7.07 (s, 1H, 5-H), 7.05 (d, 1H, J 2.0 Hz,
Ar), 6.98 (dd, 1H, J 8.4, 2.0 Hz, Ar), 6.92 (d, 1H, J 8.4 Hz,
Ar), 3.75 (s, 3H, OCH3), 3.74 (s, 3H, OCH3), 2.66 (s, 3H,
NCH3). IR (KBr) ν 1697 (C=O), 1654 (C=O), 1631 (C=C).
MS (APCI) m/z 378.1 [M+H]+. Anal. Calcd. for C22H19NO5:
C, 70.02; H, 5.07; N, 3.71. Found: C, 70.17; H, 5.11; N,
3.84.
6-Methyl-2-phenyl-5-(2-thienyl)-5,6-dihydropyrano[2,3-
c]pyrrole-4,7-dione (5{1-6-1}).
Yield 22%; mp 222-223 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.95-8.02 (m, 2H, Ar), 7.46-7.59 (m, 4H, Ar),
7.24 (d, 1H, J 3.5 Hz, Ar), 7.13 (s, 1H, 3-H), 7.08 (s, 1H, 5-
H), 7.00 (dd, 1H, J 5.1, 3.5 Hz, Ar), 2.71(s, 3H, NCH3).
IR (KBr) ν 1701 (C=O), 1658 (C=O), 1627 (C=C). MS
(APCI) m/z 324.0 [M+H]+. Anal. Calcd. for C18H13NO3S:
C, 66.86; H, 4.05; N, 4.33. Found: C, 67.01; H, 4.02; N,
4.39.
6-Methyl-2-phenyl-5-pyridin-3-yl-5,6-dihydropyrano-
[2,3-c]pyrrole-4,7-dione (5{1-7-1}).
Yield 43%; mp 243-245 °C. 1H NMR (400 MHz,
DMSO-d6) δ 8.56-8.60 (m, 1H, Ar), 8.51 (dd, 1H, J 4.8,
1.6 Hz, Ar), 7.95-8.02 (m, 2H, Ar), 7.46-7.59 (m, 4H, Ar),
7.37 (dd, 1H, J 7.9, 4.8 Hz, Ar), 7.19 (s, 1H, 5-H), 7.13
(s, 1H, 3-H), 2.74 (s, 3H, NCH3). IR (KBr) ν 1704 (C=O),
1654 (C=O), 1631 (C=C). Anal. Calcd. for C19H14N2O3:
C, 71.69; H, 4.43; N, 8.80. Found: C.71.56; H, 5.51; N,
8.92.
2-(4-Methoxyphenyl)-6-methyl-5-phenyl-5,6-dihydropy-
rano[2,3-c]pyrrole-4,7-dione (5{2-1-1}).
Yield 52%; mp 221-223 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.92 (d, 2H, J 8.4 Hz, Ar), 7.43-7.51 (m, 2H,
Ar), 7.30-7.41 (m, 3H, Ar), 7.12 (d, 2H, J 8.4 Hz, Ar), 7.06
(s, 1H, 3-H), 6.94 (s, 1H, 5-H), 3.85 (s, 3H, OCH3), 2.64 (s,
3H, NCH3). IR (KBr) ν 1706 (C=O), 1663 (C=O), 1628
(C=C), 1605 (C=C). MS (APCI) m/z 348.1 [M+H]+. Anal.
Calcd. for C21H17NO4: C, 72.61; H, 4.93; N, 4.03. Found: C,
72.49; H, 5.01; N, 4.14.
5-(4-Chlorophenyl)-2-(4-methoxyphenyl)-6-methyl-5,6-
dihydropyrano[2,3-c]pyrrole-4,7-dione (5{2-2-1}).
Yield 46%; mp 215-216 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.93 (d, 2H, J 8.5 Hz, Ar), 7.51 (d, 2H, J 8.3
Hz, Ar), 7.43 (d, 2H, J 8.3 Hz, Ar), 7.23 (s, 1H, 5-H), 7.13
(d, 2H, J 8.5 Hz, Ar), 7.01 (s, 1H, 3-H), 3.85 (s, 3H, OCH3),
2.63 (s, 3H, NCH3). IR (KBr) ν 1705 (C=O), 1661 (C=O),
1627 (C=C), 1606 (C=C). Anal. Calcd. for C21H16ClNO4: C,
66.06; H, 4.22; N, 3.67. Found: C, 65.90; H, 4.25; N, 3.75.
2,5-Bis(4-methoxyphenyl)-6-methyl-5,6-dihydropyrano-
[2,3-c]pyrrole-4,7-dione (5{2-3-1}).
Yield 45%; mp 217-218 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.92 (d, 2H, J 8.4 Hz, Ar), 7.38 (d, 2H, J 8.4
Hz, Ar), 7.12 (d, 2H, J 8.4 Hz, Ar), 7.01 (s, 1H, 3-H), 6.95
(s, 1H, 5-H), 6.91 (d, 2H, J 8.4 Hz, Ar), 3.85 (s, 3H, OCH3),
3.75 (s, 3H, OCH3), 2.69 (s, 3H, NCH3). IR (KBr) ν 1705
(C=O), 1659 (C=O), 1629 (C=C), 1604 (C=C). MS (APCI)
m/z 378.0 [M+H]+. Anal. Calcd. for C22H19NO5: C, 70.02;
H, 5.07; N, 3.71. Found: C, 69.84; H, 5.13; N, 3.82.
6-Ethyl-2,5-diphenyl-5,6-dihydropyrano[2,3-c]pyrrole-
4,7-dione (5{1-1-2}).
Yield 51%; mp 194-195 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.93-8.02 (m, 2H, Ar), 7.50-7.59 (m, 3H, Ar),
7.43-7.48 (m, 2H, Ar), 7.26-7.37 (m, 3H, Ar), 7.04 (s, 1H,
3-H), 6.99 (s, 1H, 5-H), 3.29-3.40 (m, 1H, NCH2) ), 2.41-
2.47 (m, 1H, NCH2), 1.02 (t, 3H, J 7.2 Hz, CH3). IR (KBr)
ν 1716 (C=O), 1663 (C=O), 1620 (C=C). MS (APCI) m/z
332.0 [M+H]+. Anal. Calcd. for C21H17NO3: C, 76.12; H,
5.17; N, 4.23. Found: C, 76.24; H, 5.21; N, 4.35.
5-(4-Chlorophenyl)-6-ethyl-2-phenyl-5,6-dihydropyrano-
[2,3-c]pyrrole-4,7-dione (5{1-2-2}).
Yield 56%; mp 210-212 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.96-8.01 (m, 2H, Ar), 7.57-7.63 (m, 3H, Ar),
7.56 (d, 2H, J 8.5 Hz, Ar), 7.42 (d, 2H, J 8.5 Hz, Ar), 7.29
(s, 1H, 5-H), 7.13 (s, 1H, 3-H), 3.32-3.38 (m, 1H, NCH2),
3.28-3.32 (m, 1H, NCH2), 0.94 (t, 3H, J 7.1 Hz, CH3).
IR (KBr) ν 1716 (C=O), 1664 (C=O), 1619 (C=C).
MS (APCI) m/z 368.2 ([M(37Cl)+H]+, 30), 366.2
([M(35Cl)+H]+, 100). Anal. Calcd. for C21H16ClNO3:
C, 68.95; H, 4.41; N. 3.83. Found: C, 68.81; H, 4.39; N,
3.97.
2,5,6-Triphenyl-5,6-dihydropyrano[2,3-c]pyrrole-4,7-di-
one (5{1-1-3}).
Yield 51%; mp 272-274 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.97-8.02 (m, 2H, Ar), 7.57-7.65 (m, 5H, Ar),
7.39-7.43 (m, 2H, Ar), 7.32-7.37 (m, 2H, Ar), 7.15-7.30 (m,
4H, Ar), 7.13 (s, 1H, 3-H), 6.52 (s, 1H, 5-H). IR (KBr)
ν 1707 (C=O), 1667 (C=O), 1633 (C=C). MS (APCI) m/z
380.2 [M+H]+. Anal. Calcd. for C25H17NO3: C, 79.14; H,
4.52. Found: C, 79.26; H, 4.59.
6-(4-Methoxyphenyl)-2,5-diphenyl-5,6-dihydropyrano-
[2,3-c]pyrrole-4,7-dione (5{1-1-4}).
Yield 54%; mp 255-257 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.97-8.04 (m, 2H, Ar), 7.56-7.66 (m, 3H, Ar),
ISSN 1814-9758. Ukr. Bioorg. Acta, 2021, Vol. 16, N 2
10
7.49 (d, 2H, J 8.9 Hz, Ar), 7.36-7.41 (m, 2H, Ar), 7.21-7.28
(m, 3H, Ar), 7.14 (s, 1H, 3-H), 6.99 (d, 2H, J 8.9 Hz, Ar),
6.44 (s, 1H, 5-H), 3.70 (s, 3H, OCH3). IR (KBr) ν 1708
(C=O), 1670 (C=O), 1630 (C=C). MS (APCI) m/z 410.1
[M+H]+. Anal. Calcd. for C26H19NO4: C, 76.27; H, 4.68.
Found: C, 76.42; H, 4.65.
2-(4-Methoxyphenyl)-5,6-diphenyl-5,6-dihydropyrano-
[2,3-c]pyrrole-4,7-dione (5{2-1-3}).
Yield 47%; mp 251-253 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.93 (d, 2H, J 8.4 Hz, Ar), 7.59-7.62 (m, 2H,
Ar), 7.27-7.36 (m, 4H, Ar), 7.06-7.24 (m, 7H, 3-H, Ar),
6.49 (s, 1H, 5-H), 3.74 (s, 3H, OCH3). IR (KBr) ν 1705
(C=O), 1662 (C=O), 1629 (C=C), 1605 (C=C). MS (APCI)
m/z 410.0 [M+H]+. Anal. Calcd. for C26H19NO4: C, 76.27;
H, 4.68. Found: C, 76.35; H, 4.59.
2,5-Diphenyl-6-(1,3-thiazol-2-yl)-5,6-dihydropyrano-
[2,3-c]pyrrole-4,7-dione (5{1-1-5}).
Yield 42%; mp 288-289 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.89-8.21 (m, 2H, Ar), 7.59-7.64 (m, 3H, Ar),
7.42-7.51 (m, 3H, Ar), 7.39 (d, 1H, J 3.0 Hz, Ar), 7.23-7.27
(m, 3H, Ar), 7.19 (s, 1H, 3-H), 6.37 (s, 1H, 5-H). IR (KBr)
ν 1720 (C=O), 1680 (C=O), 1630 (C=C). MS (APCI) m/z
387.1 [M+H]+. Anal. Calcd. for C22H14N2O3S: C, 68.38; H,
3.65; N, 7.25; S, 8.30. Found: C, 68.54; H, 3.71; N, 7.39;
S, 8.45.
5-(4-Chlorophenyl)-2-phenyl-6-(1,3-thiazol-2-yl)-5,6-di-
hydropyrano[2,3-c]pyrrole-4,7-dione (5{1-2-5}).
Yield 47%; mp 259-260 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.89-8.21 (m, 2H, Ar), 7.59-7.66 (m, 3H, Ar),
7.54 (d, 2H, J 8.1 Hz, Ar), 7.47 (d, 1H, J 3.0 Hz, Ar), 7.41
(d, 1H, J 3.0 Hz, Ar), 7.35 (d, 2H, J 8.1 Hz, Ar), 7.21 (s,
1H, 3-H), 6.39 (s, 1H, 5-H). IR (KBr) ν 1722 (C=O), 1679
(C=O), 1630 (C=C). MS (APCI) m/z 423.0([M(37Cl)+H]+;
30), 421.0 ([M(35Cl)+H]+, 100) Anal. Calcd. for
C22H13ClN2O3S: C, 62.78; H, 3.11; N, 6.66; S, 7.62. Found:
C, 62.63; H, 3.15; N, 6.79; S, 7.80.
6-(4,5-Dimethyl-1,3-thiazol-2-yl)-2,5-diphenyl-5,6-dihy-
dropyrano[2,3-c]pyrrole-4,7-dione (5{1-1-6}).
Yield 49%; mp 255-257 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.96-8.05 (m, 2H, Ar), 7.56-7.65 (m, 3H, Ar),
7.40-7.48 (m, 2H, Ar), 7.25-7.32 (m, 3H, Ar), 7.13 (s, 1H,
3-H), 6.29 (s, 1H, 5-H), 2.24 (s, 3H, CH3), 2.06 (s, 3H,
CH3). IR (KBr) ν 1718 (C=O), 1661 (C=O), 1631 (C=C).
MS (APCI) m/z 415.0 [M+H]+. Anal. Calcd. for
C24H18N2O3S: C, 69.55; H, 4.38; N, 6.76; S, 7.74. Found:
C, 69.39; H, 4.37; N, 6.84; S, 7.91.
6-(5-Methyl-1,3,4-thiadiazol-2-yl)-2,5-diphenyl-5,6-dihy-
dropyrano[2,3-c]pyrrole-4,7-dione (5{1-1-7}).
Yield 46%; mp: 259-260 °C. 1H NMR (400 MHz,
DMSO-d6) δ 7.95-8.06 (m, 2H, Ar), 7.54-7.63 (m, 3H, Ar),
7.40-7.48 (m, 2H, Ar), 7.26-7.33 (m, 3H, Ar), 7.15 (s, 1H,
3-H), 6.38 (s, 1H, 5-H), 2.37 (s, 3H, CH3). IR (KBr)
ν 1721 (C=O), 1673 (C=O), 1633 (C=C). MS (APCI) m/z
402.1 [M+H]+. Anal. Calcd. for C22H15N3O3S: C, 65.82;
H, 3.77; N, 10.47; S, 7.99. Found: C, 65.67; H, 3.64; N,
10.61; S, 8.13.
Notes
The authors declare no conflict interest.
Author contributions. R. N. V.: synthesis of compo-
unds, investigation, formal analysis, writing of the most part
of the manuscript, editing. S. Ya. P.: synthesis of
compounds, investigation, formal analysis. Ya. O. P.:
synthesis of compounds, investigation, formal analysis,
writing of the manuscript. V. S. B.: conceptualization,
supervision.
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Перетворення заміщених 3-гідрокси-4-[(2Е)-3-арилпроп-2-еноїл]-1,5-дигідро-2Н-
пірол-2-онів під дією I2/ДМСО у похідні 2-арил-5,6-дигідропірано[2,3-с]пірол-4,7-
діонів
Р. Н. Виджак, C. Я. Панчишин*, Я. О. Простота, В. С. Броварець
Інститут біоорганічної хімії та нафтохімії ім. В.П. Кухаря НАН України, вул. Мурманська, 1, Київ, 02094, Україна
Резюме: Представлено препаративний метод одержання різноманітних похідних 2-арил-дигідропірано[2,3-c]пірол-4,7-діонів шляхом I2/ДМСО
окислювальної циклоконденсації 3-гідрокси-4[(2E)-3-арилпроп-2-еніл]-1,5-дигідро-2Н-пірол-2-онів. Цей протокол сумісний з широким колом
замісників і відкриває реальний синтетичний шлях для одержання цільових сполук в запропонованих умовах. Всі синтезовані сполуки були
виділені та очищені за допомогою кристалізації без застосування інших методів очищення. Показано, що метильні групи гетероциклічних
фрагментів у вказаних умовах не окиснюються. В той же час даним методом неможливо ввести замісники, що можуть легко окиснюють ся або
приєднюють йод в умовах реакції. Представлений метод є досить зручним та ефективним підходом до синтезу маловивчених дигідропірано[2,3 -
c]пірол-4,7-діонів. Вихідні N-алкіл- та N-гетерилзаміщені 3-гідрокси-4[(2E)-3-арилпроп-2-еніл]-1,5-дигідро-2Н-пірол-2-они були одержані
шляхом трьохкомпонентної циклоконденсації естерів цінамоїлпіровиноградних кислот, ароматичних або гетероциклічних альдегідів та
аліфатичних чи гетероциклічних амінів. N-Арил похідні пірол-2-онів синтезували із відповідних азометинів. Будову синтезованих сполук
підтверджено методами ІЧ та ЯМР 1Н спектроскопії.
Ключові слова: багатокомпонентна циклізація; окислювальна циклізація при дії I2/ДМСО.
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| id | oai:ojs2.bioorganica.com.ua:article-20 |
| institution | Ukrainica Bioorganica Acta |
| keywords_txt_mv | keywords |
| language | English |
| last_indexed | 2026-07-20T01:00:33Z |
| publishDate | 2021 |
| publisher | V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine |
| record_format | ojs |
| resource_txt_mv | bioorganicacomua/ae/5de5b30d6ba68dfb3526ed11b54f7cae.pdf |
| spelling | oai:ojs2.bioorganica.com.ua:article-202026-07-19T14:56:53Z Transformation of substituted 3-hydroxy-4-[(2E)-3-arylprop-2-enoyl]-1,5-dihydro-2H-pyrrol-2-ones by the action of I2/DMSO into derivatives 2-aryl-5,6-dihydropyrano[2,3-c]pyrrole-4,7-diones Перетворення заміщених 3-гідрокси-4-[(2Е)-3-арилпроп-2-еноїл]-1,5-дигідро-2Н-пірол-2-онів під дією I2/ДМСО у похідні 2-арил-5,6-дигідропірано[2,3-с]пірол-4,7-діонів Vydzhak, Roman N. Panchishin, Svitlana Ya. Prostota, Yaroslav O. Brovarets, Volodymyr S. multicomponent cyclization pyrano[2,3-c]pyrrole I2/DMSO oxidative cyclization багатокомпонентна циклізація окислювальна циклізація при дії I2/ДМСО The effective and simple synthetic preparative procedure for obtaining of various derivatives of 2-aryl-5,6-dihydropyrano[2,3-c]pyrrole-4,7-diones applying the I2/DMSO oxidation of 3-hydroxy-4-[(2E)-3-arylprop-2-enoyl]-1,5-dihydro-2H-pyrrol-2-ones was developed. This protocol was found to be compatible with a wide range of substituents and gave the reliable synthetic pathway for the obtaining of target compounds with a wide range of substituents under mild conditions. All obtained substances can be easily isolated and purified by crystallization without application of more complex and labour intensive purification methods Представлено препаративний метод одержання різноманітних похідних 2-арил-дигідропірано[2,3-c]пірол-4,7-діонів шляхом I2/ДМСО окислювальної циклоконденсації 3-гідрокси-4[(2E)-3-арилпроп-2-еніл]-1,5-дигідро-2Н-пірол-2-онів. Цей протокол сумісний з широким колом замісників і відкриває реальний синтетичний шлях для одержання цільових сполук в запропонованих умовах. Всі синтезовані сполуки були виділені та очищені за допомогою кристалізації без застосування інших методів очищення. Показано, що метильні групи гетероциклічних фрагментів у вказаних умовах не окиснюються. В той же час даним методом неможливо ввести замісники, що можуть легко окиснюються або приєднюють йод в умовах реакції. Представлений метод є досить зручним та ефективним підходом до синтезу маловивчених дигідропірано[2,3-c]пірол-4,7-діонів. Вихідні N-алкіл- та N-гетерилзаміщені 3-гідрокси-4[(2E)-3-арилпроп-2-еніл]-1,5-дигідро-2Н-пірол-2-они були одержані шляхом трьохкомпонентної циклоконденсації естерів цінамоїлпіровиноградних кислот, ароматичних або гетероциклічних альдегідів та аліфатичних чи гетероциклічних амінів. N-Арил похідні пірол-2-онів синтезували із відповідних азометинів. Будову синтезованих сполук підтверджено методами ІЧ та ЯМР 1Н спектроскопії V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine 2021-12-27 Article Article application/pdf https://bioorganica.com.ua/index.php/journal/article/view/20 10.15407/bioorganica2021.02.003 Ukrainica Bioorganica Acta; Vol. 16 No. 2 (2021): Ukrainica Bioorganica Acta; 3-11 Ukrainica Bioorganica Acta; Том 16 № 2 (2021): Ukrainica Bioorganica Acta; 3-11 1814-9766 1814-9758 10.15407/bioorganica2021.02 en https://bioorganica.com.ua/index.php/journal/article/view/20/24 Copyright (c) 2021 Roman N. Vydzhak, Svitlana Ya. Panchishin, Yaroslav O. Prostota, Volodymyr S. Brovarets https://creativecommons.org/licenses/by/4.0 |
| spellingShingle | багатокомпонентна циклізація окислювальна циклізація при дії I2/ДМСО Vydzhak, Roman N. Panchishin, Svitlana Ya. Prostota, Yaroslav O. Brovarets, Volodymyr S. Перетворення заміщених 3-гідрокси-4-[(2Е)-3-арилпроп-2-еноїл]-1,5-дигідро-2Н-пірол-2-онів під дією I2/ДМСО у похідні 2-арил-5,6-дигідропірано[2,3-с]пірол-4,7-діонів |
| title | Перетворення заміщених 3-гідрокси-4-[(2Е)-3-арилпроп-2-еноїл]-1,5-дигідро-2Н-пірол-2-онів під дією I2/ДМСО у похідні 2-арил-5,6-дигідропірано[2,3-с]пірол-4,7-діонів |
| title_alt | Transformation of substituted 3-hydroxy-4-[(2E)-3-arylprop-2-enoyl]-1,5-dihydro-2H-pyrrol-2-ones by the action of I2/DMSO into derivatives 2-aryl-5,6-dihydropyrano[2,3-c]pyrrole-4,7-diones |
| title_full | Перетворення заміщених 3-гідрокси-4-[(2Е)-3-арилпроп-2-еноїл]-1,5-дигідро-2Н-пірол-2-онів під дією I2/ДМСО у похідні 2-арил-5,6-дигідропірано[2,3-с]пірол-4,7-діонів |
| title_fullStr | Перетворення заміщених 3-гідрокси-4-[(2Е)-3-арилпроп-2-еноїл]-1,5-дигідро-2Н-пірол-2-онів під дією I2/ДМСО у похідні 2-арил-5,6-дигідропірано[2,3-с]пірол-4,7-діонів |
| title_full_unstemmed | Перетворення заміщених 3-гідрокси-4-[(2Е)-3-арилпроп-2-еноїл]-1,5-дигідро-2Н-пірол-2-онів під дією I2/ДМСО у похідні 2-арил-5,6-дигідропірано[2,3-с]пірол-4,7-діонів |
| title_short | Перетворення заміщених 3-гідрокси-4-[(2Е)-3-арилпроп-2-еноїл]-1,5-дигідро-2Н-пірол-2-онів під дією I2/ДМСО у похідні 2-арил-5,6-дигідропірано[2,3-с]пірол-4,7-діонів |
| title_sort | перетворення заміщених 3-гідрокси-4-[(2е)-3-арилпроп-2-еноїл]-1,5-дигідро-2н-пірол-2-онів під дією i2/дмсо у похідні 2-арил-5,6-дигідропірано[2,3-с]пірол-4,7-діонів |
| topic | багатокомпонентна циклізація окислювальна циклізація при дії I2/ДМСО |
| topic_facet | multicomponent cyclization pyrano[2,3-c]pyrrole I2/DMSO oxidative cyclization багатокомпонентна циклізація окислювальна циклізація при дії I2/ДМСО |
| url | https://bioorganica.com.ua/index.php/journal/article/view/20 |
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