СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ
The Knoevenagel condensation reaction between dehydracetic acid and aromatic aldehydes is described in this work. The reaction is carried out directly between dehydroacetic acid and aromatic aldehydes in the presence of organic bases. The optimal conditions for the Knoevenagel reaction based on dehy...
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| Date: | 2021 |
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| Main Authors: | , , , , , , , , |
| Format: | Article |
| Language: | English |
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V.I.Vernadsky Institute of General and Inorganic Chemistry
2021
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| Online Access: | https://ucj.org.ua/index.php/journal/article/view/309 |
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Ukrainian Chemistry Journal| _version_ | 1871465708795199488 |
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| author | Tretyakova, Iryna Chernii, Viktor Fedosova, Natalia Denisenko, Iryna Dovbii, Yan Kovalska, Vladyslava Chernii, Svitlana Pekhnyo, Vasyl Starukhin, Alexandr |
| author_facet | Tretyakova, Iryna Chernii, Viktor Fedosova, Natalia Denisenko, Iryna Dovbii, Yan Kovalska, Vladyslava Chernii, Svitlana Pekhnyo, Vasyl Starukhin, Alexandr |
| author_institution_txt_mv | [
{
"author": "Iryna Tretyakova",
"institution": "IGIC"
},
{
"author": "Viktor Chernii",
"institution": "V. I. Vernadskii Institute of General and Inorganic Chemistry NAS of Ukraine, Kyiv, Ukraine"
},
{
"author": "Natalia Fedosova",
"institution": "V. I. Vernadskii Institute of General and Inorganic Chemistry NAS of Ukraine, Kyiv, Ukraine"
},
{
"author": "Iryna Denisenko",
"institution": "V. I. Vernadskii Institute of General and Inorganic Chemistry NAS of Ukraine, Kyiv, Ukraine"
},
{
"author": "Yan Dovbii",
"institution": "V. I. Vernadskii Institute of General and Inorganic Chemistry NAS of Ukraine, Kyiv, Ukraine"
},
{
"author": "Vladyslava Kovalska",
"institution": "Institute of Molecular Biology and Genetics NAS of Ukraine, Kyiv, Ukraine"
},
{
"author": "Svitlana Chernii",
"institution": "Institute of Molecular Biology and Genetics NAS of Ukraine, Kyiv, Ukraine"
},
{
"author": "Vasyl Pekhnyo",
"institution": "V. I. Vernadskii Institute of General and Inorganic Chemistry NAS of Ukraine, Kyiv, Ukraine"
},
{
"author": "Alexandr Starukhin",
"institution": "B. I. Stepanov Institute of Physics NAS of Belarus, Minsk, Belarus"
}
] |
| author_sort | Tretyakova, Iryna |
| baseUrl_str | https://ucj.org.ua/index.php/journal/oai |
| collection | OJS |
| datestamp_date | 2026-07-22T08:23:46Z |
| description | The Knoevenagel condensation reaction between dehydracetic acid and aromatic aldehydes is described in this work. The reaction is carried out directly between dehydroacetic acid and aromatic aldehydes in the presence of organic bases. The optimal conditions for the Knoevenagel reaction based on dehydroacetic acid and various aldehydes were determined. Twenty-one chalcones with substituents of different nature were synthesized. The composition and structure of the obtained compounds were determined. All characteristic signals of chalcones are present in the 1H NMR spectra of the obtained compounds registered in CDCl3 and DMSO-d6: OH groups in the range of 18.7–16.5 ppm, CH proton – 6.3–5.9 ppm, and methyl group of the pyran cycle 2.3–2.2 ppm. The corresponding signals of methine protons and aryl substituents are also present in the spectra. The most sensitive to solvent changes is the OH proton bound by an intramolecular hydrogen bond to the carbonyl group of the pyran ring. Signals in DMSO are usually shifted by 0.1–1.0 ppm in a stronger field compared to CDCl3 for dehydroacetic acid and chalcones based on it. CH proton signals are shifted by approximately 0.3 ppm in a weaker field, and the signals of the protons of the methyl group are almost insensitive to the solvent. The optical properties of obtained compounds were investigated in DMF, MeOH, MeCN. The synthesized chalcones absorb light in the visible range 330–490 nm with molar extinction coefficients of 3.5–4.5. The solvatochromic effects for most of them are weak – the position of the maximum changes by less than 10 nm. The electron-donor substituents in the phenyl ring (-NMe2 and -NEt2) shift the absorption maximum bathochromically by almost 100 nm compared to others in all investigated solvents. |
| doi_str_mv | 10.33609/2708-129X.87.05.2021.3-14 |
| first_indexed | 2025-09-24T17:43:39Z |
| format | Article |
| fulltext |
3
UDC 547-316, 547.812.6 doi: 10.33609/2708-129X.87.05.2021.3-14
SYNTHESIS AND PROPERTIES OF CHALCONES BASED
ON DEHYDROACETIC ACID
V. Ya. Chernii1*, I. M. Tretyakova1, N. M. Fedosova1, I. M. Denysenko1, Ya. M. Dovbii1,
V. B. Kovalska1,2, S. V. Chernii1,2, V. I. Pekhnyo1, A. S. Starukhin3
1V. I. Vernadskii Institute of General and Inorganic Chemistry NAS of Ukraine, Kyiv, Ukraine
2Institute of Molecular Biology and Genetics NAS of Ukraine, Kyiv, Ukraine
3B. I. Stepanov Institute of Physics NAS of Belarus, Minsk, Belarus
*e-mail: v.chernii@gmail.com
The Knoevenagel condensation reaction between dehydracetic acid and aromatic alde-
hydes is described in this work. The reaction is carried out directly between dehydroacetic
acid and aromatic aldehydes in the presence of organic bases. The optimal conditions for the
Knoevenagel reaction based on dehydroacetic acid and various aldehydes were determined.
Twenty-one chalcones with substituents of different nature were synthesized. The composi-
tion and structure of the obtained compounds were determined. All characteristic signals of
chalcones are present in the 1H NMR spectra of the obtained compounds registered in CDCl3
and DMSO-d6: OH groups in the range of 18.7–16.5 ppm, CH proton – 6.3–5.9 ppm, and
methyl group of the pyran cycle 2.3–2.2 ppm. The corresponding signals of methine protons
and aryl substituents are also present in the spectra. The most sensitive to solvent changes
is the OH proton bound by an intramolecular hydrogen bond to the carbonyl group of the
pyran ring. Signals in DMSO are usually shifted by 0.1–1.0 ppm in a stronger field compared
to CDCl3 for dehydroacetic acid and chalcones based on it. CH proton signals are shifted by
approximately 0.3 ppm in a weaker field, and the signals of the protons of the methyl group
are almost insensitive to the solvent. The optical properties of obtained compounds were
investigated in DMF, MeOH, MeCN. The synthesized chalcones absorb light in the visible
range 330–490 nm with molar extinction coefficients of 3.5–4.5. The solvatochromic effects
for most of them are weak – the position of the maximum changes by less than 10 nm. The
electron-donor substituents in the phenyl ring (-NMe2 and -NEt2) shift the absorption ma
ximum bathochromically by almost 100 nm compared to others in all investigated solvents.
Keywords: dehydroacetic acid, Knoevenagel condensation, chalcones.
SYNTHESIS AND PROPERTIES OF CHALCONES BASED ON DEHYDROACETIC ACID
4 ISSN 2708-129X. Укр. хім. журн., 2021
INORGANIC CHEMISTRY
INTRODUCTION. Dehydroacetic acid
(3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one,
(DHA)) is a α‑pyrone derivative. Its structure
was first established by Hale in 1911 [1]. Сom-
plexes of dehydroacetic acid with ions of alu-
minum, zinc, copper(II), beryllium, manga
nese (II), and other metals are described in the
literature. DHA is proposed as a complexing
agent in analytical chemistry for gravimetric
determination of copper, aluminum, and be-
ryllium [2]. The corresponding mixed ligand
complexes are formed when DHA interacts with
zirconium and hafnium phthalocyanines [3].
An annealed analog of dehydroacetic acid –
3-acetyl-4-hydroxycoumarin has been pro-
posed for the determination of titanium(IV),
cerium(IV), thorium(IV), uranium(VI), and
iron(II) ions [4, 5]. X-ray diffraction data ob-
tained for dehydroacetic acid complexes with
manganese(II) (Mn(DHA)2(CH3OH)2), cad-
mium, and zinc [6, 7], confirm the formation
of chelate complexes in which the metal atom
is coordinated through 3-acetyl and 4-oxy
groups of dehydroacetic acid.
DHA is also widely used in organic che
mistry since it enters into dozens of reactions
to form very diverse classes of substances [8]
(Fig. 1).
INTRODUCTION. Dehydroacetic acid (3-acetyl-4-hydroxy-6-methyl-2H-
pyran-2-one, (DHA)) is a -pyrone derivative. Its structure was first established by
Hale in 1911 [1]. Сomplexes of dehydroacetic acid with ions of aluminum, zinc,
copper(II), beryllium, manganese (II), and other metals are described in the
literature. DHA is proposed as a complexing agent in analytical chemistry for
gravimetric determination of copper, aluminum, and beryllium [2]. The
corresponding mixed ligand complexes are formed when DHA interacts with
zirconium and hafnium phthalocyanines [3]. An annealed analog of dehydroacetic
acid – 3-acetyl-4-hydroxycoumarin has been proposed for the determination of
titanium(IV), cerium(IV), thorium(IV), uranium(VI), and iron(II) ions [4, 5]. X-ray
diffraction data obtained for dehydroacetic acid complexes with manganese(II)
(Mn(DHA)2(CH3OH)2), cadmium, and zinc [6, 7], confirm the formation of chelate
complexes in which the metal atom is coordinated through 3-acetyl and 4-oxy
groups of dehydroacetic acid.
DHA is also widely used in organic chemistry since it enters into dozens of
reactions to form very diverse classes of substances [8] (Fig. 1).
Fig. 1. Examples of dehydroacetic acid derivatives containing chelating
centers.
Some of these compounds contain -keto-enol or other fragments that may
be promising to inorganic chemists as ligands. For example, the interaction of
dehydroacetic acid with aromatic aldehydes by the Knevenagel reaction produces
the corresponding chalcones [9–14]. These are colored substances that can also
form complexes with metals [15] and boron [16]. Metal complexes have also been
widely studied not only with dehydroacetic acid [17–19] but also with its
Fig. 1. Examples of dehydroacetic acid derivatives containing chelating centers.
Some of these compounds contain β-ke-
to-enol or other fragments that may be promis-
ing to inorganic chemists as ligands. For exam-
ple, the interaction of dehydroacetic acid with
aromatic aldehydes by the Knoevenagel reaction
produces the corresponding chalcones [9–14].
These are colored substances that can also form
complexes with metals [15] and boron [16].
Metal complexes have also been widely studied
not only with dehydroacetic acid [17–19] but
also with its derivatives - Schiff bases [20-25]
and other various O, N, S donor ligands [26–28].
For dehydroacetic acid and its derivatives, an-
timicrobial [15, 29], antitumor [30, 31], antivi-
ral, in particular, anti-HIV activity [16, 32, 33],
etc., are widely studied.
V. Ya. Chernii, I. M. Tretyakova, N. M. Fedosova, I. M. Denisenko, Ya. M. Dovbii, V. B. Kovalska, S. V. Chernii, V. I. Pekhnyo, A. S. Starukhin
5https://ucj.org.ua
UCJ № 5 / Vol. 87
The interaction of chalcones with aliphatic
amines opens the pyran cycle, preserving the
chromophore fragment and forming the cor-
responding alkylamino-β-keto-enols. These
compounds have found their application to
monitor the amyloid fibril formation of pro-
teins [34, 35] and as fluorescent probes for
functional amyloid visualization in biofilm by
confocal microscopy [36].
There are two main methods for preparing
chalcones based on dehydroacetic acid by the
Knoevenagel reaction (Fig. 2).
Fig. 2. Methods of obtaining chalcones – deriva-
tives of dehydroacetic acid: activation of the methyl
group by forming boron difluoride complex (A),
the direct reaction between dehydroacetic acid and
aromatic aldehydes (B).
According to the first method, the methyl
group of dehydroacetic acid is activated by
converting dehydroacetic acid into a boron
difluoride complex [16], which reacts with
aromatic aldehydes with the formation of the
corresponding complex. In the next step, this
compound is hydrolyzed with alkalis to the
corresponding chalcone. According to the
second method, the reaction is carried out
directly between dehydroacetic acid and aro-
matic aldehydes [1] in the presence of organic
bases, for example, piperidine.
We have obtained a wide range of chalcones
with substituents of different natures in the
aromatic nucleus (Fig. 3) and investigated their
spectral properties.
Fig. 3. Molecular structures of obtained chal
kones
EXPERIMENT AND DISCUSSION OF
THE RESULTS. All characteristic signals of
chalcones are present in the 1H NMR spectra of
the obtained compounds registered in CDCl3
and DMSO-d6: OH groups in the range of
derivatives - Schiff bases [20-25] and other various O, N, S donor ligands [26–28].
For dehydroacetic acid and its derivatives, antimicrobial [15, 29], antitumor [30,
31], antiviral, in particular, anti-HIV activity [16, 32, 33], etc., are widely studied.
The interaction of chalcones with aliphatic amines opens the pyran cycle,
preserving the chromophore fragment and forming the corresponding alkylamino-
-keto-enols. These compounds have found their application to monitor the
amyloid fibril formation of proteins [34, 35] and as fluorescent probes for
functional amyloid visualization in biofilm by confocal microscopy [36].
There are two main methods for preparing chalcones based on dehydroacetic
acid by the Kneuvenagel reaction (Fig. 2).
Fig. 2. Methods of obtaining chalcones – derivatives of dehydroacetic acid:
activation of the methyl group by forming boron difluoride complex (A), the direct
reaction between dehydroacetic acid and aromatic aldehydes (B).
According to the first method, the methyl group of dehydroacetic acid is
activated by converting dehydroacetic acid into a boron difluoride complex [16],
which reacts with aromatic aldehydes with the formation of the corresponding
complex. In the next step, this compound is hydrolyzed with alkalis to the
corresponding chalcone. According to the second method, the reaction is carried
out directly between dehydroacetic acid and aromatic aldehydes [1] in the presence
of organic bases, for example, piperidine.
We have obtained a wide range of chalcones with substituents of different
natures in the aromatic nucleus (Fig. 3) and investigated their spectral properties.
Fig. 3. General scheme of synthesis of chalcones – derivatives of dehydroacetic
acid.
EXPERIMENT AND DISCUSSION OF THE RESULTS. All characteristic
signals of chalcones are present in the 1H NMR spectra of the obtained compounds
registered in CDCl3 and DMSO-d6: OH groups in the range of 18.7–16.5 ppm, CH
proton – 6.3–5.9 ppm, and methyl group of the pyran cycle 2.3–2.2 ppm (Table).
In addition, corresponding signals of methine protons and aryl substituents are also
present in the spectra. The most sensitive to solvent changes is the OH proton
bound by an intramolecular hydrogen bond to the carbonyl group of the pyran ring.
Signals in DMSO are usually shifted by 0.1–1.0 ppm in a stronger field compared
to CDCl3 for dehydroacetic acid and chalcones based on it. CH proton signals are
shifted by approximately 0.3 ppm in a weaker field, and the signals of the protons
of the methyl group are almost insensitive to the solvent.
The investigated compounds' absorption maxima in DMF are located in the
range of 348–490 nm (except for compounds with a nitro group, which have a
maximum absorption in the UV region), with extinction coefficients (log ε) in the
range of 3.93–4.46.
SYNTHESIS AND PROPERTIES OF CHALCONES BASED ON DEHYDROACETIC ACID
6 ISSN 2708-129X. Укр. хім. журн., 2021
INORGANIC CHEMISTRY
18.7–16.5 ppm, CH proton – 6.3–5.9 ppm, and
methyl group of the pyran cycle 2.3–2.2 ppm
(Table). In addition, corresponding signals of
methine protons and aryl substituents are also
present in the spectra. The most sensitive to
solvent changes is the OH proton bound by an
intramolecular hydrogen bond to the carbo
nyl group of the pyran ring. Signals in DMSO
are usually shifted by 0.1–1.0 ppm in a strong-
er field compared to CDCl3 for dehydroacetic
acid and chalcones based on it. CH proton sig-
nals are shifted by approximately 0.3 ppm in a
weaker field, and the signals of the protons of
the methyl group are almost insensitive to the
solvent.
The investigated compounds absorption
maxima in DMF are located in the range of
348–490 nm (except for compounds with a ni-
tro group, which have a maximum absorption
in the UV region), with extinction coefficients
(log ε) in the range of 3.93–4.46.
In methanol, the absorption maxima are lo-
cated between 350 and 472 nm, the extinction
coefficients (log ε) are 3.66–4.54.
Fig. 4. UV-VIS spectra of chalcones 7, 11, and 18 in dimethylformamide (C = 1•10-4M).
In acetonitrile, the absorption maxima are
in the range of 279–477 nm, the extinction co-
efficients (log ε) are 3.55–4.75. The electron-do-
nor substituents in the phenyl ring (-N(CH3)2
and -N(C2H5)2) shift the absorption maximum
bathochromically by almost 100 nm compared
to others in all investigated solvents.
Comparing the absorption spectra of one
compound in different solvents lead to the
conclusion that the solvatochromic effects for
most of them are weak - the position of the
maximum changes by less than 10 nm. How-
ever, for compounds 10, 13, and 16, the maxi-
mum is shifted to the red region in acetonitrile
by 15–17 nm compared to DMF. Moreover, for
compounds 12 and 15 the maximum is shift-
ed to the red region by 19 nm. The most sig-
nificant shift is observed for the compound
20 by 30 nm. Compound 21, in contrast, in
DMF has a red-shifted maximum in compa
rison to acetonitrile, 381 and 345 nm, respec-
tively (table).
V. Ya. Chernii, I. M. Tretyakova, N. M. Fedosova, I. M. Denisenko, Ya. M. Dovbii, V. B. Kovalska, S. V. Chernii, V. I. Pekhnyo, A. S. Starukhin
7https://ucj.org.ua
UCJ № 5 / Vol. 87
Table
The proton signals of the pyran cycle in the 1H NMR spectra and the UV-VIS data of the
obtained chalcones.
№ 1H NMR, δ, ppm UV-VIS, λ, nm (log ε)
CDCl3 DMSO CDCl3 DMSO CDCl3 DMSO DMF MeOH MeCN
OH CH Me
DHA 16.67 16.54 5.92 6.28 2.26 2.25 - - -
1 17.95 17.55 5.97 6.32 2.29 2.28 354(4,15) 350(3,96) 357(4,20)
2 17.44 16.94 6.01 6.36 2.31 2.28 357(4,03) 354(3,66) 356(3,87)
3 17.48 17.12 6.01 6.34 2.31 2.28 356(3,95) 352(3,67) 360(3,55)
4 17.42 17.04 6.01 6.34 2.32 2.28 326(4,22) 360(3,49) 361(3,55)
5 - 18.01 - 6.28 - 2.26 357(4,09) 371(4,18) 378(4,24)
6 17.86 17.66 5.95 6.28 2.27 2.26 474(3,96) 358(4,22 ) 361(4,09)
7 17.53 18.08 5.95 6.25 2.27 2.25 369(4,27) 383(4,52) 383(4,23)
8 18.13 17.78 5.93 6.29 2.26 2.26 367(4,17) 371(4,12) 376(4,21)
9 17.92 17.49 5.97 6.31 2.29 2.26 360(4,16) 356(4,06) 360(4,17)
10 18.18 17.89 5.94 6.27 2.27 2.25 366(4,21) 375(4,51) 381(4,75)
11 18.24 17.93 5.94 6.27 2.27 2.25 377(4,09) 373(3,95) 383(4,07)
12 18.16 17.80 5.96 6.18 2.26 2.18 374(4,22) 391(4,26) 393(4,49)
13 18.44 17.42 5.93 6.25 2.26 2.24 382(4,04) 396(4,24) 399(4,05)
14 17.80 17.32 5.90 6.29 2.22 2.29 360(4,16) 357(4,10) 360(4,14)
15 17.97 17.64 5.95 6.31 2.27 2.28 360(3,91) 370(4,40) 279(4,24)
16 18.11 17.78 5.94 6.28 2.27 2.25 372(4,16) 381(4,15) 387(3,96)
17 17.80 17.50 5.90 6.33 2.22 2.28 357(4,14) 354(4,19) 358(4,15)
18 18.61 18.57 5.89 6.22 2.24 2.25 474(4,29)
347(4,14)
456(4,45)
330(3,98)
465(4,25)
19 18.71 18.57 5.90 6.18 2.24 2.23 490(4,39) 472(4,54) 477(4,02)
20 17.98 17.51 5.98 6.34 2.29 2.28 348(4,08) 378(4,22) 378(3,88)
21 18.13 17.77 5.98 6.35 2.30 2.30 381(4,46) 345(4,35) 345(4,42)
The general synthesis method of dehydroacetic
acid condensed derivatives. The reactions were
performed by a slightly modified procedure giv-
en in the work [3]. 10 mmol of substituted ben-
zaldehyde was added to 10 mmol of dehydro-
acetic acid in 10 ml of n-butanol and was heated
up to boiling temperature. 10 drops of a mixture
of pyridine and piperidine (1:1 by volume) were
added to the boiling homogeneous solution and
refluxed for 2–4 h. Half of the solvent was dis-
tilled, the solution was cooled down and filtered
from fell-out crystals. The product was washed
twice on the filter with a small amount of meth-
anol and recrystallized from the DMF-ethanol
system. After that, the product was filtered,
washed on the filter with methanol, twice with
hot water, and air-dried. Data from 1H NMR
and UV-VIS spectroscopy are given in the table.
SYNTHESIS AND PROPERTIES OF CHALCONES BASED ON DEHYDROACETIC ACID
8 ISSN 2708-129X. Укр. хім. журн., 2021
INORGANIC CHEMISTRY
DHA (3-acetyl-4-hydroxy-6-methyl-2H-
pyran-2-one). 1H NMR (300 MHz, DMSO-d6)
δ 16.54 (s, 1H), 6.28 (s, 1H), 2.54 (s, 3H), 2.25
(s, 3H). 1H NMR (300 MHz, CDCl3) δ 16.67
(s, 1H), 5.92 (s, 1H), 2.64 (s, 3H), 2.26 (s, 3H).
1) 3-cinnamoyl-4-hydroxy-6-methyl-2H-
pyran- 2-one. Yield: 59 %. 1H NMR (400 MHz,
DMSO-d6) δ 17.55 (s, 1H), 8.17 (d, J = 15.8 Hz,
1H), 7.91 (d, J = 15.9 Hz, 1H), 7.79–7.66 (m,
2H), 7.59–7.37 (m, 3H), 6.32 (s, 1H), 2.28
(s, 3H). 1H NMR (300 MHz, Chloroform-d)
δ 17.95 (s, 1H), 8.32 (d, J = 15.7 Hz, 1H), 7.97
(d, J = 15.7 Hz, 1H), 7.76–7.54 (m, 2H), 7.51–
7.34 (m, 3H), 5.97 (s, 1H), 2.29 (s, 3H).
2) (E)-4-hydroxy-6-methyl-3-(3-(2-ni-
trophenyl)acryloyl)-2H-pyran-2-one. Yield:
43 %. 1H NMR (500 MHz, DMSO-d6) δ 16.94
(s, 1H), 8.20–7.99 (m, 3H), 7.95–7.81 (m, 2H),
7.73–7.62 (m, 1H), 6.36 (s, 1H), 2.28 (s, 3H).
1H NMR (300 MHz, Chloroform-d) δ 17.44
(s, 1H), 8.34 (d, J = 15.6 Hz, 1H), 8.22 (d, J =
15.5 Hz, 1H), 8.05 (d, J = 8.1 Hz, 1H), 7.85 (d,
J = 7.8 Hz, 1H), 7.76–7.64 (m, 1H), 7.57 (td, J =
7.8, 1.5 Hz, 1H), 6.01 (s, 1H), 2.31 (s, 3H).
3) (E)-4-hydroxy-6-methyl-3-(3-(3-nitro-
phenyl)acryloyl)-2H-pyran-2-one. Yield: 31 %.
1H NMR (500 MHz, DMSO-d6) δ 17.12 (s,
1H), 8.52 (s, 1H), 8.35–8.26 (m, 1H), 8.25–8.08
(m, 2H), 7.98 (d, J = 15.9 Hz, 1H), 7.78–7.68
(m, 1H), 6.34 (s, 1H), 2.28 (s, 3H). 1H NMR
(300 MHz, Chloroform-d) δ 17.48 (s, 1H),
8.47 (t, J = 2.0 Hz, 1H), 8.39 (d, J = 15.8 Hz,
1H), 8.26 (dd, J = 8.2, 3.3 Hz, 1H), 8.02 (d, J =
7.8 Hz, 1H), 7.93 (d, J = 15.8 Hz, 1H), 7.60 (t,
J = 8.0 Hz, 1H), 6.01 (s, 1H), 2.31 (s, 3H).
4) (E)-4-hydroxy-6-methyl-3-(3-(4-nitro-
phenyl)acryloyl)-2H-pyran-2-one. Yield: 20 %.
1H NMR (500 MHz, DMSO-d6) δ 17.04
(s, 1H), 8.29 (d, J = 8.3 Hz, 2H), 8.23 (d, J =
15.8 Hz, 1H), 7.97 (d, J = 8.2 Hz, 2H), 7.93 (d,
J = 16.1 Hz, 1H), 6.34 (s, 1H), 2.28 (s, 3H).
1H NMR (300 MHz, Chloroform-d) δ 17.42
(s, 1H), 8.41 (d, J = 15.8 Hz, 1H), 8.27 (d, J =
8.7 Hz, 2H), 7.91 (d, J = 15.8 Hz, 1H), 7.82 (d,
J = 8.7 Hz, 2H), 6.01 (s, 1H), 2.32 (s, 3H).
5) E)-4-hydroxy-3-(3-(2-hydroxyphenyl)
acryloyl)-6-methyl-2H-pyran-2-one. Yield: 50 %.
1H NMR (400 MHz, DMSO-d6) δ 18.01 (s, 1H),
10.52 (s, 1H), 8.53–7.86 (m, 2H), 7.58 (d, J =
7.9 Hz, 1H), 7.31 (t, J = 15.7 Hz, 1H), 6.98–6.78
(m, 2H), 6.28 (s, 1H), 2.26 (s, 3H). Insoluble in
chloroform-d.
6) (E)-4-hydroxy-3-(3-(3-hydroxyphenyl)
acryloyl)-6-methyl-2H-pyran-2-one. Yield: 39 %.
1H NMR (500 MHz, DMSO-d6) δ 17.66 (s,
1H), 9.77 (s, 1H), 8.11 (d, J = 15.8 Hz, 1H),
7.81 (d, J = 15.8 Hz, 1H), 7.28 (t, J = 8.0 Hz,
1H), 7.13 (d, J = 6.4 Hz, 2H), 6.89 (dd, 1H),
6.28 (s, 1H), 2.26 (s, 3H). 1H NMR (400 MHz,
Chloroform-d) δ 17.86 (s, 1H), 8.26 (d, J =
15.7 Hz, 1H), 7.88 (d, J = 15.7 Hz, 1H), 7.28
(t, J = 7.7 Hz, 3H), 7.15 (s, 1H), 6.97–6.86 (m,
1H), 5.95 (s, 1H), 2.27 (s, 2H).
7) (E)-4-hydroxy-3-(3-(4-hydroxyphenyl)
acryloyl)-6-methyl-2H-pyran-2-one. Yield:
21 %. 1H NMR (500 MHz, DMSO-d6) δ 18.08
(s, 1H), 10.35 (s, 1H), 8.01 (d, J = 15.7 Hz, 1H),
7.88 (d, J = 15.7 Hz, 1H), 7.59 (d, J = 8.5 Hz,
2H), 6.87 (d, J = 8.5 Hz, 2H), 6.25 (s, 1H), 2.25
(s, 3H). 1H NMR (500 MHz, Chloroform-d) δ
17.53 (s, 1H), 8.20 (d, J = 16.0 Hz, 1H), 7.94 (d,
J = 15.7 Hz, 1H), 7.62 (d, J = 7.9 Hz, 2H), 6.88
(d, J = 8.0 Hz, 2H), 5.95 (s, 1H), 2.27 (s, 3H).
8) (E)-4-hydroxy-3-(3-(2-methoxyphenyl)
acryloyl)-6-methyl-2H-pyran-2-one. Yield: 68 %.
1H NMR (400 MHz, DMSO-d6) δ 17.78 (s, 1H),
8.24 (d, J = 15.9 Hz, 1H), 8.15 (d, J = 16.0 Hz,
1H), 7.67 (dd, J = 7.7, 1.7 Hz, 1H), 7.54–7.43
(m, 1H), 7.13 (d, J = 8.4 Hz, 1H), 7.05 (t, J =
8.0 Hz, 1H), 6.29 (s, 1H), 3.89 (s, 3H), 2.26 (s,
V. Ya. Chernii, I. M. Tretyakova, N. M. Fedosova, I. M. Denisenko, Ya. M. Dovbii, V. B. Kovalska, S. V. Chernii, V. I. Pekhnyo, A. S. Starukhin
9https://ucj.org.ua
UCJ № 5 / Vol. 87
3H). 1H NMR (500 MHz, Chloroform-d) δ
18.13 (s, 1H), 8.51–8.16 (m, 2H), 7.72 (d, J =
7.7 Hz, 1H), 7.38 (t, J = 8.1 Hz, 1H), 6.98 (t, J =
7.5 Hz, 1H), 6.92 (d, J = 8.4 Hz, 1H), 5.93 (s,
1H), 3.91 (s, 3H), 2.26 (s, 3H).
9) (E)-4-hydroxy-3-(3-(3-methoxyphe-
nyl)acryloyl)-6-methyl-2H-pyran-2-one. Yield:
63 %. 1H NMR (500 MHz, DMSO-d6) δ 17.49
(s, 1H), 8.13 (d, J = 16.1 Hz, 1H), 7.86 (d, J =
15.8 Hz, 1H), 7.39 (t, J = 7.9 Hz, 1H), 7.31 (d, J
= 7.5 Hz, 1H), 7.24 (s, 1H), 7.11–6.99 (m, 1H),
6.31 (s, 1H), 3.79 (s, 3H), 2.26 (s, 3H). 1H NMR
(300 MHz, Chloroform-d) δ 17.92 (s, 1H), 8.30
(d, J = 15.7 Hz, 1H), 7.93 (d, J = 15.8 Hz, 1H),
7.41–7.26 (m, 2H), 7.23 – 7.13 (m, 1H), 6.98
(ddd, J = 7.7, 2.6, 1.5 Hz, 1H), 5.97 (s, 1H), 3.85
(s, 3H), 2.29 (s, 3H).
10) (E)-4-hydroxy-3-(3-(4-methoxyphe-
nyl)acryloyl)-6-methyl-2H-pyran-2-one.
Yield: 49 %. 1H NMR (500 MHz, DMSO-d6)
δ 17.89 (s, 1H), 8.05 (d, J = 15.7 Hz, 1H), 7.90
(d, J = 15.7 Hz, 1H), 7.69 (d, J = 8.4 Hz, 2H),
7.04 (d, J = 8.2 Hz, 2H), 6.27 (s, 1H), 3.81 (s,
3H), 2.25 (s, 3H). 1H NMR (400 MHz, Chlo-
roform-d) δ 18.18 (s, 1H), 8.20 (d, J = 15.6
Hz, 1H), 7.96 (d, J = 15.7 Hz, 1H), 7.66 (d, J =
8.8 Hz, 2H), 6.93 (d, J = 8.8 Hz, 2H), 5.94 (s,
1H), 3.86 (s, 3H), 2.27 (s, 3H).
11) (E)-4-hydroxy-6-methyl-3-(3-(4-
propoxyphenyl)acryloyl)-2H-pyran-2-one.
Yield: 65 %. 1H NMR (500 MHz, DMSO-d6)
δ 17.93 (s, 1H), 8.04 (d, J = 15.8 Hz, 1H), 7.90
(d, J = 15.7 Hz, 1H), 7.67 (d, J = 8.2 Hz, 2H),
7.02 (d, J = 8.3 Hz, 2H), 6.27 (s, 1H), 3.98 (t, J
= 6.4 Hz, 2H), 2.25 (q, 3H), 1.73 (q, J = 7.1 Hz,
2H), 0.96 (t, J = 7.2 Hz, 3H). 1H NMR (300
MHz, Chloroform-d) δ 18.24 (s, 1H), 8.20 (d,
J = 15.6 Hz, 1H), 7.96 (d, J = 15.6 Hz, 1H),
7.70–7.60 (m, 2H), 6.97–6.88 (m, 2H), 5.94 (s,
1H), 3.97 (t, J = 6.6 Hz, 2H), 2.27 (s, 3H), 1.83
(q, J = 7.1, 6.7 Hz, 2H), 1.05 (t, J = 7.4 Hz, 3H).
12) (E)-4-hydroxy-3-(3-(4-hydroxy-3-
methoxyphenyl)acryloyl)-6-methyl-2H-
pyran-2-one. Yield: 43 %. 1H NMR (500 MHz,
DMSO-d6) δ 17.80 (s, 1H), 9.87 (s, 1H), 7.93
(d, J = 15.6 Hz, 1H), 7.81 (d, J = 15.6 Hz, 1H),
7.42–7.05 (m, 2H), 6.80 (d, J = 8.1 Hz, 1H),
6.18 (s, 1H), 3.75 (s, 3H), 2.18 (s, 3H). 1H NMR
(500 MHz, Chloroform-d) δ 18.16 (s, 1H), 8.16
(d, J = 15.6 Hz, 1H), 7.92 (d, J = 15.6 Hz, 1H),
7.24–7.14 (m, 2H), 6.94 (d, J = 8.2 Hz, 1H),
5.96 (s, 1H), 5.94 (s, 1H), 3.96 (s, 3H), 2.26 (s,
3H).
13) (E)-3-(3-(2,4-dimethoxyphenyl)acry-
loyl)-4-hydroxy-6-methyl-2H-pyran-2-one.
Yield: 51 %. 1H NMR (500 MHz, DMSO-d6)
δ 17.42 (s, 1H), 8.13 (s, 2H), 7.76–7.49 (m, 1H),
6.79–6.51 (m, 2H), 6.25 (s, 1H), 3.89 (s, 3H),
3.83 (s, 3H), 2.24 (s, 3H). 1H NMR (300 MHz,
Chloroform-d) δ 18.44 (s, 1H), 8.31 (d, J =
4.0 Hz, 2H), 7.69 (d, J = 8.8 Hz, 1H), 6.55 (dd,
J = 8.6, 2.4 Hz, 1H), 6.45 (d, J = 2.4 Hz, 1H), 5.93
(s, 1H), 3.91 (s, 3H), 3.87 (s, 3H), 2.26 (s, 3H).
14) (E)-3-(3-(3,5-dimethoxyphenyl)acry-
loyl)-4-hydroxy-6-methyl-2H-pyran-2-one.
Yield: 52 %. 1H NMR (400 MHz, DMSO-d6)
δ 17.32 (s, 1H), 8.09 (d, J = 15.8 Hz, 1H), 7.82
(d, J = 15.8 Hz, 1H), 6.87 (s, 2H), 6.64 (s, 1H),
6.29 (s, 1H), 3.81 (s, 6H), 2.29 (s, 3H). 1H NMR
(500 MHz, Chloroform-d) δ 17.80 (s, 1H), 8.20
(d, J = 15.7 Hz, 1H), 7.81 (d, J = 15.7 Hz, 1H),
6.75 (s, 2H), 6.46 (s, 1H), 5.90 (s, 1H), 3.77 (s,
6H), 2.22 (s, 3H).
15) (E)-4-hydroxy-6-methyl-3-(3-(3,4,5-
trimethoxyphenyl)acryloyl)-2H-pyran-2-one.
Yield: 51 %. 1H NMR (400 MHz, DMSO-d6)
δ 17.64 (s, 1H), 8.05 (d, J = 15.5 Hz, 1H), 7.87
(d, J = 15.7 Hz, 1H), 7.06 (s, 2H), 6.31 (s, 1H),
3.84 (s, 6H), 3.73 (s, 3H), 2.28 (s, 3H). 1H NMR
(500 MHz, Chloroform-d) δ 17.97 (s, 1H), 8.20
SYNTHESIS AND PROPERTIES OF CHALCONES BASED ON DEHYDROACETIC ACID
10 ISSN 2708-129X. Укр. хім. журн., 2021
INORGANIC CHEMISTRY
(d, J = 15.6 Hz, 1H), 7.88 (d, J = 15.7 Hz, 1H),
6.89 (s, 2H), 5.95 (s, 1H), 3.91 (s, 6H), 3.89 (s,
3H), 2.27 (s, 3H).
16) (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)
acryloyl)-4-hydroxy-6-methyl-2H-pyran-
2-one. Yield: 75 %. 1H NMR (500 MHz,
DMSO-d6) δ 17.78 (s, 1H), 7.99 (d, J = 15.7
Hz, 1H), 7.85 (d, J = 15.7 Hz, 1H), 7.43–7.14
(m, 2H), 7.01 (d, J = 8.0 Hz, 1H), 6.28 (s, 1H),
6.11 (s, 2H), 2.25 (s, 3H). 1H NMR (300 MHz,
Chloroform-d) δ 18.11 (s, 1H), 8.14 (d, J =
15.6 Hz, 1H), 7.88 (d, J = 15.6 Hz, 1H), 7.22 (d,
J = 1.8 Hz, 1H), 7.16 (dd, J = 8.1, 1.7 Hz, 1H),
6.83 (d, J = 8.0 Hz, 1H), 6.03 (s, 2H), 5.94 (s,
1H), 2.27 (s, 3H).
17) (E)-3-(3-(4-fluorophenyl)acryloyl)-
4-hydroxy-6-methyl-2H-pyran-2-one. Yield:
49 %. 1H NMR (300 MHz, DMSO-d6) δ 17.50
(s, 1H), 8.12 (d, J = 15.8 Hz, 1H), 7.92 (d, J =
15.9 Hz, 1H), 7.88–7.74 (m, 2H), 7.34 (t, J =
8.8 Hz, 2H), 6.33 (s, 1H), 2.28 (s, 3H). 1H NMR
(500 MHz, Chloroform-d) δ 17.80 (s, 1H), 8.17
(d, J = 15.7 Hz, 1H), 7.85 (d, J = 15.7 Hz, 1H),
7.62 (dd, J = 8.5, 5.5 Hz, 2H), 7.04 (t, J = 8.4 Hz,
2H), 5.90 (s, 1H), 2.22 (s, 3H).
18) (E)-3-(3-(4-(dimethylamino)phenyl)
acryloyl)-4-hydroxy-6-methyl-2H-pyran-
2-one. Yield: 32 %. 1H NMR (500 MHz,
DMSO-d6) δ 18.57 (s, 1H), 7.95 (s, 2H), 7.59
(d, J = 9.0 Hz, 2H), 6.79 (d, J = 9.0 Hz, 2H),
6.22 (s, 1H), 3.34 (s, 6H), 2.25 (s, 3H). 1H NMR
(500 MHz, Chloroform-d) δ 18.61 (s, 1H), 8.10
(d, J = 15.4 Hz, 1H), 7.99 (d, J = 15.3 Hz, 1H),
7.60 (d, J = 8.9 Hz, 2H), 6.67 (d, J = 9.0 Hz, 2H),
5.89 (s, 1H), 3.06 (s, 6H), 2.24 (s, 3H).
19) (E)-3-(3-(4-(diethylamino)phenyl)ac
ryloyl)-4-hydroxy-6-methyl-2H-pyran-2-one.
Yield: 49 %. 1H NMR (500 MHz, DMSO-d6)
δ 18.57 (s, 1H), 7.92 (s, 2H), 7.54 (d, J = 8.6
Hz, 2H), 6.74 (d, J = 8.5 Hz, 2H), 6.18 (s, 1H),
3.42 (q, J = 7.0 Hz, 4H), 2.23 (s, 3H), 1.11 (t,
J = 6.9 Hz, 6H). 1H NMR (500 MHz, Chloro-
form-d) δ 18.71 (s, 1H), 8.36–7.79 (m, 2H),
7.59 (d, J = 9.0 Hz, 2H), 6.65 (d, J = 8.5 Hz, 2H),
5.90 (d, J = 0.9 Hz, 1H), 3.43 (q, J = 7.1 Hz, 4H),
2.24 (s, 3H), 1.21 (t, J = 7.1 Hz, 6H)
20) (E)-4-hydroxy-6-methyl-3-(3-(naph-
thalen-1-yl)acryloyl)-2H-pyran-2-one. Yield:
31 %. 1H NMR (500 MHz, DMSO-d6) δ 17.51
(s, 1H), 8.67 (d, J = 15.6 Hz, 1H), 8.39–8.16 (m,
2H), 8.08 (d, J = 8.1 Hz, 1H), 7.99 (dd, J = 22.5,
7.1 Hz, 2H), 7.72–7.50 (m, 3H), 6.34 (s, 1H), 2.28
(s, 3H). 1H NMR (300 MHz, Chloroform-d) δ
17.98 (s, 1H), 8.85 (d, J = 15.5 Hz, 1H), 8.42 (d, J
= 15.5 Hz, 1H), 8.29 (d, J = 7.7 Hz, 1H), 8.04 (d, J
= 7.3 Hz, 1H), 7.99–7.80 (m, 2H), 7.66–7.50 (m,
3H), 5.98 (s, 1H), 2.29 (s, 3H).
21) (E)-4-hydroxy-6-methyl-3-(3-(pyren-
1-yl)acryloyl)-2H-pyran-2-one. Yield: 68 %.
1H NMR (300 MHz, DMSO-d6) δ 17.77 (s, 1H),
9.02 (d, J = 15.4 Hz, 1H), 8.64 (d, J = 9.4 Hz,
1H), 8.53–8.36 (m, 6H), 8.35–8.20 (m, 3H),
6.35 (s, 1H), 2.30 (s, 3H). 1H NMR (500 MHz,
Chloroform-d) δ 18.13 (s, 1H), 9.17 (d, J = 15.4
Hz, 1H), 8.68–8.49 (m, 3H), 8.30–7.99 (m,
7H), 5.98 (s, 1H), 2.30 (s, 3H).
CONCLUSIONS
The optimal conditions for the Knoevenagel
reaction based on dehydroacetic acid and va
rious aldehydes were determined. Twenty-one
chalcones with substituents of different nature
in the aromatic nucleus were obtained and
characterized by 1H NMR spectroscopy. The
optical properties of synthesized compounds
were investigated in DMF, MeOH, MeCN. It
was found that the absorption maxima are in
the visible range from 330 to 490 nm with a
weak solvatochromic effect for these com-
pounds in studied solvents.
V. Ya. Chernii, I. M. Tretyakova, N. M. Fedosova, I. M. Denisenko, Ya. M. Dovbii, V. B. Kovalska, S. V. Chernii, V. I. Pekhnyo, A. S. Starukhin
11https://ucj.org.ua
UCJ № 5 / Vol. 87
The work was supported by the NAS of
Ukraine project № 07-03-20/21 of joint
competition of projects of the NAS of
Ukraine – NAS of Belarus.
СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ
НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ
В. Я. Черній1*, І. М. Третякова1,
Н. М. Федосова1, І. М. Денисенко1,
Я. М. Довбій1, В. Б. Ковальська1,2,
С. В. Черній1,2, В. І. Пехньо1, А. С. Старухін3
1Інститут загальної та неорганічної хімії
імені В. І. Вернадського НАН України, Київ,
Україна
2Інститут молекулярної біології та гене-
тики НАН України, Київ, Україна
3Інститут фізики ім. Б. І. Степанова НАН
Білорусі, Мінськ, Білорусь
*e-mail: v.chernii@gmail.com
У роботі досліджено реакцію конденсації
Кневенагеля між дегідрацетовою кислотою
та ароматичними альдегідами. Отримано
21 халкон із замісниками різної природи.
Встановлено склад та будову отриманих
сполук, досліджено їхні оптичні властивості
в різних розчинниках. Синтезовані халкони
поглинають світло у видимому діапазоні
330–490 нм із молярними коефіцієнтами
екстинкції 3,5–4,5.
Ключові слова: дегідрацетова кислота,
конденсація Кневенагеля, халкони.
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Стаття надійшла 17.06.2021.
|
| id | oai:ojs2.1444248.nisspano.web.hosting-test.net:article-309 |
| institution | Ukrainian Chemistry Journal |
| keywords_txt_mv | keywords |
| language | English |
| last_indexed | 2026-07-23T01:06:20Z |
| publishDate | 2021 |
| publisher | V.I.Vernadsky Institute of General and Inorganic Chemistry |
| record_format | ojs |
| resource_txt_mv | ucjorgua/e7/30bdcb8e14221928f2795ef3bbdf3ae7.pdf |
| spelling | oai:ojs2.1444248.nisspano.web.hosting-test.net:article-3092026-07-22T08:23:46Z SYNTHESIS AND PROPERTIES OF CHALCONES BASED ON DEHYDROACETIC ACID СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ Tretyakova, Iryna Chernii, Viktor Fedosova, Natalia Denisenko, Iryna Dovbii, Yan Kovalska, Vladyslava Chernii, Svitlana Pekhnyo, Vasyl Starukhin, Alexandr dehydroacetic acid, Knoevenagel condensation, chalcones. The Knoevenagel condensation reaction between dehydracetic acid and aromatic aldehydes is described in this work. The reaction is carried out directly between dehydroacetic acid and aromatic aldehydes in the presence of organic bases. The optimal conditions for the Knoevenagel reaction based on dehydroacetic acid and various aldehydes were determined. Twenty-one chalcones with substituents of different nature were synthesized. The composition and structure of the obtained compounds were determined. All characteristic signals of chalcones are present in the 1H NMR spectra of the obtained compounds registered in CDCl3 and DMSO-d6: OH groups in the range of 18.7–16.5 ppm, CH proton – 6.3–5.9 ppm, and methyl group of the pyran cycle 2.3–2.2 ppm. The corresponding signals of methine protons and aryl substituents are also present in the spectra. The most sensitive to solvent changes is the OH proton bound by an intramolecular hydrogen bond to the carbonyl group of the pyran ring. Signals in DMSO are usually shifted by 0.1–1.0 ppm in a stronger field compared to CDCl3 for dehydroacetic acid and chalcones based on it. CH proton signals are shifted by approximately 0.3 ppm in a weaker field, and the signals of the protons of the methyl group are almost insensitive to the solvent. The optical properties of obtained compounds were investigated in DMF, MeOH, MeCN. The synthesized chalcones absorb light in the visible range 330–490 nm with molar extinction coefficients of 3.5–4.5. The solvatochromic effects for most of them are weak – the position of the maximum changes by less than 10 nm. The electron-donor substituents in the phenyl ring (-NMe2 and -NEt2) shift the absorption maximum bathochromically by almost 100 nm compared to others in all investigated solvents. V.I.Vernadsky Institute of General and Inorganic Chemistry 2021-06-25 Article Article Inorganic Chemistry Неорганическая химия Неорганічна хімія application/pdf https://ucj.org.ua/index.php/journal/article/view/309 10.33609/2708-129X.87.05.2021.3-14 Ukrainian Chemistry Journal; Vol. 87 No. 5 (2021): Ukrainian Chemistry Journal; 3-14 Украинский химический журнал; ##issue.vol## 87 ##issue.no## 5 (2021): Ukrainian Chemistry Journal; 3-14 Український хімічний журнал; Том 87 № 5 (2021): Український хімічний журнал; 3-14 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/309/168 Copyright (c) 2021 Iryna Tretyakova, Viktor Chernii, Natalia Fedosova, Iryna Denisenko, Yan Dovbii, Vladyslava Kovalska, Svitlana Chernii, Vasyl Pekhnyo, Alexandr Starukhin https://creativecommons.org/licenses/by-nc/4.0 |
| spellingShingle | Tretyakova, Iryna Chernii, Viktor Fedosova, Natalia Denisenko, Iryna Dovbii, Yan Kovalska, Vladyslava Chernii, Svitlana Pekhnyo, Vasyl Starukhin, Alexandr СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ |
| title | СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ |
| title_alt | SYNTHESIS AND PROPERTIES OF CHALCONES BASED ON DEHYDROACETIC ACID |
| title_full | СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ |
| title_fullStr | СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ |
| title_full_unstemmed | СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ |
| title_short | СИНТЕЗ ТА ВЛАСТИВОСТІ ХАЛКОНІВ НА ОСНОВІ ДЕГІДРАЦЕТОВОЇ КИСЛОТИ |
| title_sort | синтез та властивості халконів на основі дегідрацетової кислоти |
| topic_facet | dehydroacetic acid Knoevenagel condensation chalcones. |
| url | https://ucj.org.ua/index.php/journal/article/view/309 |
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