Синтез нового 1-бензоїлгексагідро-2Н-піроло[3,4-d]піримідин-2,4(3Н)-діону
We report an efficient [3+2] cycloaddition involving non-stabilized electron-rich azomethine ylides and 1,3-dibenzoyl-pyrimidine-2,4(1H,3H)-dione. The 1,3-dipole was prepared in situ under TFA catalysis, and we obtained the product in good yield and with full control of the regioselectivity
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V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine
2025
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Ukrainica Bioorganica Acta| _version_ | 1871193625842417664 |
|---|---|
| author | Melnychuk, Pavlo V. Shablykin, Oleg V. |
| author_facet | Melnychuk, Pavlo V. Shablykin, Oleg V. |
| author_institution_txt_mv | [
{
"author": "Pavlo V. Melnychuk",
"institution": "V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kyiv, Ukraine"
},
{
"author": "Oleg V. Shablykin",
"institution": "V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kyiv, Ukraine"
}
] |
| author_sort | Melnychuk, Pavlo V. |
| baseUrl_str | https://bioorganica.com.ua/index.php/journal/oai |
| collection | OJS |
| datestamp_date | 2026-07-19T14:56:55Z |
| description | We report an efficient [3+2] cycloaddition involving non-stabilized electron-rich azomethine ylides and 1,3-dibenzoyl-pyrimidine-2,4(1H,3H)-dione. The 1,3-dipole was prepared in situ under TFA catalysis, and we obtained the product in good yield and with full control of the regioselectivity |
| doi_str_mv | 10.15407/bioorganica2025.01.046 |
| first_indexed | 2025-09-17T09:28:20Z |
| format | Article |
| fulltext |
ISSN 1814-9758. Ukr. Bioorg. Acta, 2025, Vol. 20, N 1
UDC 547.854.4+547.857.4
DOI: https://doi.org/10.15407/bioorganica2025.01.046
46
Ukrainica Bioorganica Acta
www.bi oorgan ica .org .ua
SHORT COMMUNICATION
Synthesis of novel 1-benzoylhexahydro-2H-pyrrolo[3,4-d]pyrimidine-
2,4(3H)-dione
Pavlo V. Melnychuk*, Oleg V. Shablykin
V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kyiv, Ukraine
Abstract: We report an efficient [3+2] cycloaddition involving non-stabilized electron-rich azomethine ylides and 1,3-dibenzoyl-
pyrimidine-2,4(1H,3H)-dione. The 1,3-dipole was prepared in situ under TFA catalysis, and we obtained the product in good yield and
with full control of the regioselectivity.
Keywords: 1-benzoylhexahydro-2H-pyrrolo[3,4-d]pyrimidine-2,4(3H)-dione; [3+2] cycloaddition; azomethine ylide; bicyclic pyrrolidine.
Introduction
The pursuit of novel synthetic methodologies for the
preparation of nitrogen-containing heterocycles remains a
central focus in modern organic and medicinal chemistry.
Among such compounds, uracil derivatives stand out as
important representatives of naturally occurring pyrimidine
systems. They continue to attract strong scientific interest
due to their wide range of biological activities and
promising pharmacological potential.
1,3-Dipolar cycloaddition reactions are well-known and
widely used for the construction of five-membered
heterocycles. Reactions with azomethine ylides have
become especially popular due to their ability to form
pyrrolidine rings in a single step with good regio- and
stereoselectivity [1-5]. Pyrrolidine scaffolds represent
biologically relevant motifs that are commonly found in
numerous bioactive compounds and emerging heterocyclic
frameworks of pharmaceutical interest [6-8]. The structures
of more than 50 drugs contain the pyrrolidine fragment.
Uracil-based compounds exhibit a wide range of
Received:
Revised:
Accepted:
Published online:
17.04.2025
30.04.2025
27.05.2025
30.06.2025
Corresponding author. Tel.: +380-98-854-5189;
e-mail: melnichukpavlo@ukr.net (P.V. Melnychuk)
ORCID: 0000-0001-9197-6022
biological activities including antiviral (Sofosbuvir, a
uracil-based nucleotide analog) and antitumour (Efudex,
fluorouracil-based) examples of which are shown in Figure
1. To date, 264 bioactive compounds containing an uracil
fragment have been reported, highlighting the relevance and
continued interest in the investigation of this class of
compounds [9]. Modifications of uracil at positions 5 and 6
have already been partially studied, but to our knowledge,
the [3+2] cycloaddition reaction involving a double bond at
position 5 and 6 is poorly understood.
In a study [10], the [3+2] cycloaddition was performed
on 3´,5´-bis-o-silylthymidines using highly reactive non-
stabilized azomethine ylide which was generated from
trimethylamine N-oxide to obtain N-methyl nucleoside
O
ONHP
O
O
O
O
OH
F
HN N
O
O
Efudex
antimethabolite, thymidylate synthase inhibitor
(actinic keratosis, superficial basal cell carcinoma)
Sofosbuvir
nucleotide analog, HCV NS5B polymerase inhibitor
(hepatitis C therapy)
HN
N
H
O
O
F
Figure 1. Examples of bioactive uracil-based compounds.
© Melnychuk P.V. 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.
P.V. Melnychuk, O.V. Shablykin
47
HN
N
H
O
O
N
N
O
O
Bz
Bz
N
N
O
O
Bz
Bz
N Bn
Bz-Cl
ACN, Py
N+
CH2
-
Bn
TFA, DCM
1 2 3
Scheme 1. Synthesis of 1,3-dibenzoyl-6-benzylhexahydro-2H-pyrrolo[3,4-d]pyrimidine-2,4(3H)-dione (3).
N
N
O
O
Bz
Bz
N Bn
3
N
HN
N Boc
O
O
Bz
N
HN
NH
O
O
Bz
Boc2O
H2, Pd(10%), 10 atm,
THF, NMM, 50 °C
4 5
H Cl
DCM
HCl
Scheme 2. Synthesis of 1-benzoylhexahydro-2H-pyrrolo[3,4-d]pyrimidine-2,4(3H)-dione hydrochloride (5).
pyrrolidines. The problem with this method is that the
resulting pyrrolidines can no longer be selectively modified
at the nitrogen atom, and the generation of azomethine ylide
requires the prior preparation of lithium diisopropylamide
and work at -78 °C.
In another study [11], the [3+2] cycloaddition was
performed using nitrone dipole to the formation of fused
isoxazolidines and the cycloaddition took place with
complete regioselectivity and with stereospecific generation
of two consecutive stereocenters what was deduced by the
coupling constant values in 1H NMR spectra between newly
formed ring juncture atoms.
Only a few examples of uracil derivatives bearing a
fused pyrrolidine ring have been reported in the literature,
therefore we aimed to develop a novel synthetic approach to
access these previously unexplored structures.
We report an efficient [3+2] cycloaddition involving
unstabilized electron-rich azomethine ylide and 1,3-di-
benzoylpyrimidine-2,4(1H,3H)-dione. The 1,3-dipole was
generated in situ using trifluoroacetic acid (TFA) as a
catalyst, and the product was obtained in a good yield and
regioselectivity control. The obtained reaction products can
be selectively modified at each of the nitrogen atoms.
Results and Discussion
In this paper we present our investigations and
development of the effective approach to synthesize 1-ben-
zoylhexahydro-2H-pyrrolo[3,4-d]pyrimidine-2,4(3H)-dione
(5) via [3+2] cycloaddition between nonstabilized N-benzyl
azomethyne ylide and 1,3-dibenzoyluracil.
Initially, our aim was to attempt a 3+2 cycloaddition
reaction on unprotected uracil, drawing an analogy with
pyridone, where the double bond is activated. However,
after applying all available protocols for this reaction, we
consistently obtained either unreacted uracil or a complex
mixture of products, from which the isolation of individual
compounds proved difficult. As a result, we decided to
carry out the transformation on dibenzoyl-protected uracil,
as this approach allows for the subsequent selective removal
of the protecting groups.
So the synthesis of condensed N-benzyl pyrrolidine deri-
vative based on dibenzoyluracil was initiated by the intro-
duction of a benzoyl protecting group (Scheme 1).
This was accomplished in acetonitrile using pyridine and
benzoyl chloride according to known procedure [12]. The
subsequent [3+2] cycloaddition was carried out in DCM at
0 °C in the presence of a catalytic amount of TFA, which
was used to generate unstable N-benzyl azomethine ylide
from N-benzyl-1-methoxy-N-((trimethylsilyl)methyl)meth-
anamine to obtain 1,3-dibenzoyl-6-benzylhexahydro-2H-
pyrrolo[3,4-d]pyrimidine-2,4(3H)-dione (3). Structure was
confirmed by analyzing with 2D NMR (COSY, HSQC,
NOE) (Figure 2).
N
N
O
O
Bz
Bz
N Bn
H
H
H
H
3.41
2.76
3.64
3.14
4.89
nOe
nOe
nOe
Figure 2. NMR correlations for 1,3-dibenzoyl-6-benzylhexahyd-
ro-2H-pyrrolo[3,4-d]pyrimidine-2,4(3H)-dione (3).
All attempts to remove the benzyl and benzoyl protecting
groups to obtain the corresponding amine as a base proved
to be challenging. In all cases either the starting material 3
was recovered, or complex mixture were formed, from
which the target 1-benzoylhexahydro-2H-pyrrolo[3,4-
d]pyrimidine-2,4(3H)-dione (5) could not be isolated
(Scheme 2).
However, when catalytic hydrogenation over palladium
was performed in the presence of di-tert-butyl dicarbonate
(Boc2O) as an amine-trapping reagent in an autoclave under
heating, the removal of the benzyl protecting group
occurred along with the selective cleavage of one benzoyl
group. This transformation afforded tert-butyl 1-benzoyl-
2,4-dioxooctahydro-6H-pyrrolo[3,4-d]pyrimidine-6-carbo-
ISSN 1814-9758. Ukr. Bioorg. Acta, 2025, Vol. 20, N 1
48
xylate (4), whose structure was confirmed by analyzing
with 2D NMR (COSY, HSQC, ROE) (Figure 3).
N
N
O
O
H
N
3.48
3.18
nOe
O
Boc
3.48
3.80
3.01
4.82
11.11
Figure 3. NMR correlations for tert-butyl 1-benzoyl-2,4-dioxo-
octahydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate (4).
In the absence of Boc2O, the removal of the benzyl
protecting group did not occur, and in some cases, partial
cleavage of the benzoyl group was observed. Subsequent
treatment of compound 4 with 4M hydrochloric acid in
dioxane provided the target compound 1-benzoylhexa-
hydro-2H-pyrrolo[3,4-d]pyrimidine-2,4(3H)-dione (5) as
HCl salt.
Conclusions
In summary, we have developed an efficient [3+2]
cycloaddition-based approach toward the synthesis of
previously undescribed 1-benzoyl-substituted pyrrolo[3,4-
d]pyrimidine derivatives. The obtained target compound
can be selectively and sequentially modified at multiple
functional groups, providing convenient access to a wide
range of potentially bioactive molecules derived from this
heterocyclic scaffold. Our results are expected to stimulate
further exploration of uracil derivatives fused with a
pyrrolidine ring as promising scaffolds for the design and
development of novel bioactive compounds in medicinal
chemistry.
Notes
Acknowledgments and finances. We would like to
thank Enamine Ltd. for the material and technical support
for the synthetic part of this work.
The authors declare no conflict of interest.
Experimental section
All reagents and solvents were purchased from Enamine
Ltd. (www.enamine.net). TLC characterization was
performed with pre-coated silica gel GF254 (0.2mm). For
column flash chromatography Silica gel 230-400mesh was
used. 1H NMR spectra were recorded at 400, 500, or 600
MHz (Varian).13C NMR spectra were recorded at 100, 126,
or 151 MHz (Varian). 1H NMR chemical shifts are
calibrated using residual undeuterated solvents CHCl3 (δ =
7.26 ppm) or DMSO (δ = 2.50 ppm). 13C NMR chemical
shifts for 13C NMR are reported relative to the central
CHCl3 (δ = 77.16 ppm) or DMSO (δ = 39.52 ppm).
Coupling constants are given in hertz. LC-MS spectra were
recorded on an Agilent 1100 Series HPLC equipped with a
diode array and Agilent LC/MSD SL mass selective
detector, ionization method – chemical ionization at
atmospheric pressure, m/z scan range from 80 to 1000.
Synthesis
1,3-Dibenzoylpyrimidine-2,4(1H,3H)-dione (2).
To 900 ml of dry acetonitrile 60 g (0.54 mol) of compo-
und 1 was added. To this suspension was added pyridine
338.7 g (4.28 mol) first and then 225.7 g (1.6 mol) of ben-
zoyl chloride was slowly added dropwise. The reaction
mixture was stirred at room temperature for 2 days. The sol-
vent was removed in vacuo and the residue was purified by
silica gel column chromatography (eluent was hexane with
a gradient of ethyl acetate from 0 to 70%) to obtain 150 g (
0.47 mol, 87% ) of 2.1H NMR (500 MHz, CDCl3) δ 7.93 (t,
J = 8.1 Hz, 3H), 7.77 (d, J = 7.7 Hz, 2H), 7.66 (t, J = 7.5
Hz, 1H), 7.61 (t, J = 7.5 Hz, 1H), 7.48 (dt, J = 19.7, 7.7 Hz,
4H), 6.07 (d, J = 8.3 Hz, 1H). LCMS (M+H)+ : 321.
1,3-Dibenzoyl-6-benzylhexahydro-2H-pyrrolo[3,4-d]py-
rimidine-2,4(3H)-dione (3).
To 100 ml of dry DCM 10 g (0.031 mol) of compound 2
and 11.11 g (0.047 mol) of N-benzyl-1-methoxy-N-((trime-
thylsilyl)methyl)methanamine were added. The reaction
mixture was cooled to 0 °C in an ice-water bath and 0.36 g
(3.1 mmol) of trifluoroacetic acid was added dropwise at
this temperature. The mixture was stirred for 16 h at room
temperature. The mixture was neutralized with a 0.1 M
solution of NaHCO3. The organic layer was washed with
brine (1 × 100 mL), dried over Na2SO4, and concentrated
under reduced pressure. The residue was purified by
column chromatography (eluent was CHCl3 with a gradient
of ACN from 0 to 70%) to obtain 8.2 g (0.018 mol, 58%) of
compound 3.1H NMR (600 MHz, CDCl3) δ 8.01-7.97 (d, J
= 7.3 Hz, 2H), 7.66-7.60 (m, 3H), 7.49 (t, J = 7.5 Hz, 1H),
7.44 (t, J = 7.8 Hz, 2H), 7.42-7.28 (m, 7H), 4.89 (td, J =
8.6, 4.6 Hz, 1H), 3.86 (d, J = 12.8 Hz, 1H), 3.63 (t, J = 10.9
Hz, 2H), 3.41 (dd, J = 8.6, 5.0 Hz, 1H), 3.18-3.09 (m, 2H),
2.76 (dd, J = 9.3, 5.2 Hz, 1H).13C NMR (151 MHz, CDCl3)
δ 172.44, 170.22, 168.36, 150.00, 137.60, 135.13, 134.48,
132.49, 131.51, 130.56, 129.12, 128.72, 128.59, 128.34,
128.30, 127.54, 60.02, 59.56, 57.61, 53.54, 43.56. LCMS
(M+H)+ : 454.4
Tert-butyl 1-benzoyl-2,4-dioxooctahydro-6H-pyrrolo-
[3,4-d]pyrimidine-6-carboxylate (4).
The compound 3 was dissolved in THF (80 mL) at
autoclave and 7.89 g (0.036 mol) of di-tert-butyl
decarbonate and 1.82 g (0.018 mol) of 4-methylmorpholine
were added. Then 0.8 g of Pd/C (10%) was added to the
solution. The mixture was degassed and filled with H2 and
heated 50 °C for 1 d. Pd/C was filtered, and the reaction
mixture was concentrated under reduced pressure and
purified by silica gel column chromatography (eluent was
CHCl3 with a gradient of ACN from 0 to 15%) to obtain 4.3
g (0.012 mol, 66%) of compound 4.1H NMR (600 MHz,
DMSO-d6) δ 11.11 (s, 1H), 7.70 (d, J = 7.6 Hz, 2H), 7.54 (t,
J = 7.4 Hz, 1H), 7.43 (t, J = 7.6 Hz, 2H), 4.84 (m, 1H), 3.84
http://www.enamine.net/
P.V. Melnychuk, O.V. Shablykin
49
(m, 2H), 3.48 (m, 2H), 3.02 (m, 1H), 1.39 (d, J = 8.1 Hz,
9H).13C NMR (151 MHz, DMSO-d6) δ 173.11, 171.25,
153.60, 150.50, 135.79, 79.57, 60.20, 48.77, 48.42, 46.52,
46.18, 40.41, 40.27, 40.13, 7.92. LCMS (M+H)+ : 360.4
1-Benzoylhexahydro-2H-pyrrolo[3,4-d]pyrimidine-
2,4(3H)-dione hydrochloride (5).
1 M HCl in dioxane (20 mL) was added to the solution
of 4 g (0.011 mol) 4 in 40 ml DCM and the mixture was
stirred overnight at room temperature. The product as
hydrochloride salt was filtered off, and triturated MTBE to
obtain 2.55 g (9.8 mmol, 88%) of compound 5. 1H NMR
(500 MHz, DMSO-d6) δ 11.27 (s, 1H), 10.01-9.47 (m, 2H),
7.71 (d, J = 7.7 Hz, 2H), 7.55 (t, J = 7.4 Hz, 1H), 7.44 (t, J
= 7.7 Hz, 2H), 4.86 (q, J = 8.5 Hz, 1H), 3.76-3.5 (m, 4H),
3.08 (d, J = 12.9 Hz, 1H). LCMS (M+H)+ : 260.4.
References
1. Huisgen, R. 1,3-Dipolar Cycloadditions: Past and Future. Angew.
Chem. Int. Ed. 1963, 2, 565-598.
2. Huisgen R.; Grashey R.; Laur P.; Leitermann H. 1.3-Dipolare
Additionen der Azomethin-imine. Angew. Chem. 1960, 72, 416-417
(in German).
3. Padwa A.; Pearson W.H. Synthetic Applications of 1,3-Dipolar
Cycloaddition Chemistry Toward Heterocycles and Natural
Products. The Chemistry of Heterocyclic Compounds. Vol. 59, John
Wiley & Sons, Inc., 2003.
4. Li H.; Wu J. (3+2)-Cycloaddition Reactions of Oxyallyl Cations.
Synthesis 2020, 47, 22-33.
5. Meyer A.G.; Ryan J.H. 1,3-Dipolar Cycloaddition Reactions of
Azomethine Ylides with Carbonyl Dipolarophiles Yielding
Oxazolidine Derivatives. Molecules. 2016, 21, 935-988.
6. US Patent No 2009/0247577 A1. Pyrrolidine derivatives useful as
bace inhibitors / Rogel O.; Rondeau J.-M.; Rueeger H.; Simic O.;
Sirockin F.; Tintelnot-Blomley M. Patent appl. No 12/303495
04.06.2007. Publ. 01.10.2009.
7. Arun Y.; Bhaskar G.; Balachandran C.; Ignacimuthu S.; Perumal
P.T. Facile one-pot synthesis of novel dispirooxindole-pyrrolidine
derivatives and their antimicrobial and anticancer activity against
A549 human lung adenocarcinoma cancer cell line. Bioorg. Med.
Chem. Lett. 2013, 23, 1839-1845.
8. Stylianakis I., et al. Spiro[pyrrolidine-2,2'-adamantanes]: synthesis,
anti-influenza virus activity and conformational properties. Bioorg.
Med. Chem. Lett. 2003, 13, 1699-1703.
9. Knox, C., et al. DrugBank 6.0: the DrugBank Knowledgebase for
2024. Nucleic Acids Res., 2024, 52, D1265-D1275.
10. Negron, G., et al. 1, 3-Dipolar cycloaddition reactions of 3′, 5′-bis-o-
silyl thymidines. synthesis of novel azabicyclic compounds. Synth.
Commun. 2002, 32, 1977-1984.
11. Kuprianowicz, M.; Kaźmierczak, M.; Wójtowicz-Rajchel, H. The
nitrogen inversion in fused isoxazolidinyl derivatives of substituted
uracil: synthesis, NMR and computational analysis. Struct. Chem.
2016, 27, 1265-1278.
12. Cruickshank, K.A.; Jiricny, J.; Reese, C.B. The benzoylation of
uracil and thymine, Tetrahedron Lett., 1984, 25, 681-684.
Синтез нового 1-бензоїлгексагідро-2Н-піроло[3,4-d]піримідин-2,4(3Н)-діону
П.В. Мельничук*, О.В. Шабликін
Інститут біоорганічної хімії та нафтохімії ім. В.П. Кухаря НАН України, Київ, Україна
Резюме: Досліджено ефективне [3+2] циклоприєднання за участю нестабілізованого, багатого на електрони азометинового іліду та 1,3-дибензої-
лпіримідин-2,4(1H,3H)-діону. 1,3-Диполь було одержано in situ під дією каталітичної кількості трифтороцтової кислоти, що дозволило отримати
продукт з високим виходом та повною регіоселективністю.
Ключові слова: 1-гексагідро-2H-піроло[3,4-d]піримідин-2,4(3H)-діон; [3+2] циклоприєднання; азометиновий ілід; конденсований піролідин.
|
| id | oai:ojs2.bioorganica.com.ua:article-99 |
| institution | Ukrainica Bioorganica Acta |
| keywords_txt_mv | keywords |
| language | English |
| last_indexed | 2026-07-20T01:01:41Z |
| publishDate | 2025 |
| 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/4e/1959e8b57f259c44ccd47eaa2397ef4e.pdf |
| spelling | oai:ojs2.bioorganica.com.ua:article-992026-07-19T14:56:55Z Synthesis of novel 1-benzoylhexahydro-2H-pyrrolo[3,4-d]pyrimidine-2,4(3H)-dione Синтез нового 1-бензоїлгексагідро-2Н-піроло[3,4-d]піримідин-2,4(3Н)-діону Melnychuk, Pavlo V. Shablykin, Oleg V. 1-benzoylhexahydro-2H-pyrrolo[3,4-d]pyrimidine-2,4(3H)-dione [3 2] cycloaddition azomethine ylide bicyclic pyrrolidine 1-гексагідро-2H-піроло[3,4-d]піримідин-2,4(3H)-діон [3 2] циклоприєднання азометиновий ілід конденсований піролідин We report an efficient [3+2] cycloaddition involving non-stabilized electron-rich azomethine ylides and 1,3-dibenzoyl-pyrimidine-2,4(1H,3H)-dione. The 1,3-dipole was prepared in situ under TFA catalysis, and we obtained the product in good yield and with full control of the regioselectivity Досліджено ефективне [3+2] циклоприєднання за участю нестабілізованого, багатого на електрони азометинового іліду та 1,3-дибензої-лпіримідин-2,4(1H,3H)-діону. 1,3-Диполь було одержано in situ під дією каталітичної кількості трифтороцтової кислоти, що дозволило отримати продукт з високим виходом та повною регіоселективністю V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine 2025-06-30 Article Article application/pdf https://bioorganica.com.ua/index.php/journal/article/view/99 10.15407/bioorganica2025.01.046 Ukrainica Bioorganica Acta; Vol. 20 No. 1 (2025): Ukrainica Bioorganica Acta; 46-49 Ukrainica Bioorganica Acta; Том 20 № 1 (2025): Ukrainica Bioorganica Acta; 46-49 1814-9766 1814-9758 10.15407/bioorganica2025.01 en https://bioorganica.com.ua/index.php/journal/article/view/99/94 Copyright (c) 2025 Pavlo V. Melnychuk, Oleg V. Shablykin https://creativecommons.org/licenses/by/4.0 |
| spellingShingle | 1-гексагідро-2H-піроло[3,4-d]піримідин-2,4(3H)-діон [3 2] циклоприєднання азометиновий ілід конденсований піролідин Melnychuk, Pavlo V. Shablykin, Oleg V. Синтез нового 1-бензоїлгексагідро-2Н-піроло[3,4-d]піримідин-2,4(3Н)-діону |
| title | Синтез нового 1-бензоїлгексагідро-2Н-піроло[3,4-d]піримідин-2,4(3Н)-діону |
| title_alt | Synthesis of novel 1-benzoylhexahydro-2H-pyrrolo[3,4-d]pyrimidine-2,4(3H)-dione |
| title_full | Синтез нового 1-бензоїлгексагідро-2Н-піроло[3,4-d]піримідин-2,4(3Н)-діону |
| title_fullStr | Синтез нового 1-бензоїлгексагідро-2Н-піроло[3,4-d]піримідин-2,4(3Н)-діону |
| title_full_unstemmed | Синтез нового 1-бензоїлгексагідро-2Н-піроло[3,4-d]піримідин-2,4(3Н)-діону |
| title_short | Синтез нового 1-бензоїлгексагідро-2Н-піроло[3,4-d]піримідин-2,4(3Н)-діону |
| title_sort | синтез нового 1-бензоїлгексагідро-2н-піроло[3,4-d]піримідин-2,4(3н)-діону |
| topic | 1-гексагідро-2H-піроло[3,4-d]піримідин-2,4(3H)-діон [3 2] циклоприєднання азометиновий ілід конденсований піролідин |
| topic_facet | 1-benzoylhexahydro-2H-pyrrolo[3,4-d]pyrimidine-2,4(3H)-dione [3 2] cycloaddition azomethine ylide bicyclic pyrrolidine 1-гексагідро-2H-піроло[3,4-d]піримідин-2,4(3H)-діон [3 2] циклоприєднання азометиновий ілід конденсований піролідин |
| url | https://bioorganica.com.ua/index.php/journal/article/view/99 |
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