Переключаємі за рахунок умов багатокомпонентні реакції 5-аміно-3-(метилтіо)-1,2,4-триазолу, ароматичних альдегідів та піровиноградної кислоти
The multicomponent reactions of 5-amino-3-methylthio-1,2,4-triazole with aromatic aldehydes and pyruvic acid were studied using conventional thermal heating and ultrasonic activation at room temperature. Under conventional heating, dihydrotriazolopyrimidine derivatives were formed in both two- and t...
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| Формат: | Стаття |
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V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine
2020
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Ukrainica Bioorganica Acta| _version_ | 1871193571653058560 |
|---|---|
| author | Sakhno, Yana I. Mykhailenko, Maksym V. Kolosov, Maksim A. Shvets, Elena H. Musatov, Vladimir I. Chorna, Natalia V. Desenko, Sergey M. Chebanov, Valentyn A. |
| author_facet | Sakhno, Yana I. Mykhailenko, Maksym V. Kolosov, Maksim A. Shvets, Elena H. Musatov, Vladimir I. Chorna, Natalia V. Desenko, Sergey M. Chebanov, Valentyn A. |
| author_institution_txt_mv | [
{
"author": "Yana I. Sakhno",
"institution": "State Scientific Institution “Institute for Single Crystals” of the NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine"
},
{
"author": "Maksym V. Mykhailenko",
"institution": "State Scientific Institution “Institute for Single Crystals” of the NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine; V.N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61077, Ukraine"
},
{
"author": "Maksim A. Kolosov",
"institution": "V.N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61077, Ukraine"
},
{
"author": "Elena H. Shvets",
"institution": "V.N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61077, Ukraine"
},
{
"author": "Vladimir I. Musatov",
"institution": "State Scientific Institution “Institute for Single Crystals” of the NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine"
},
{
"author": "Natalia V. Chorna",
"institution": "State Scientific Institution “Institute for Single Crystals” of the NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine"
},
{
"author": "Sergey M. Desenko",
"institution": "State Scientific Institution “Institute for Single Crystals” of the NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine"
},
{
"author": "Valentyn A. Chebanov",
"institution": "State Scientific Institution “Institute for Single Crystals” of the NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine; V.N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61077, Ukraine"
}
] |
| author_sort | Sakhno, Yana I. |
| baseUrl_str | https://bioorganica.com.ua/index.php/journal/oai |
| collection | OJS |
| datestamp_date | 2026-07-19T14:56:53Z |
| description | The multicomponent reactions of 5-amino-3-methylthio-1,2,4-triazole with aromatic aldehydes and pyruvic acid were studied using conventional thermal heating and ultrasonic activation at room temperature. Under conventional heating, dihydrotriazolopyrimidine derivatives were formed in both two- and three-component treatments. In the case of ultrasonic activation, the multicomponent reaction led to the formation of 7-hydroxytetrahydrotriazolopyrimidines |
| doi_str_mv | 10.15407/bioorganica2020.02.022 |
| first_indexed | 2025-07-17T12:19:39Z |
| format | Article |
| fulltext |
ISSN 1814-9758. Ukr. Bioorg. Acta, 2020, Vol. 15, N 2
UDC 547.826
DOI: https://doi.org/10.15407/bioorganica2020.02.022
22
Ukrainica Bioorganica Acta
www.bi oorgan ica .org .ua
RESEARCH ARTICLE
Condition-based switching the multicomponent reactions
of 5-amino-3-(methylthio)-1,2,4-triazole, aromatic aldehydes,
and pyruvic acid
Yana I. Sakhno1, Maksym V. Mykhailenko1,2, Maksim A. Kolosov2, Elena H. Shvets2,
Vladimir I. Musatov1, Natalia V. Chorna1, Sergey M. Desenko1 and Valentyn A. Chebanov1,2*
1 State Scientific Institution “Institute for Single Crystals” of the NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine
2 V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61077, Ukraine
Abstract: The multicomponent reactions of 5-amino-3-methylthio-1,2,4-triazole with aromatic aldehydes and pyruvic acid were studied
using conventional thermal heating and ultrasonic activation at room temperature. Under conventional heating, dihydrotriazolopyrimidine
derivatives were formed in both two- and three-component treatments. In the case of ultrasonic activation, the multicomponent reaction led
to the formation of 7-hydroxytetrahydrotriazolopyrimidines.
Keywords: 5-Amino-3-(methylthio)-1,2,4-triazole; multicomponent reaction; ultrasonication; pyruvic acid; heterocyclization.
Introduction
Pyrimidine derivatives and their sulfur analogs have
attracted much attention because of their wide range of
biological activities involving antibacterial [1], anti-
inflammatory [2-3], analgesic [3], antitumour [4-5], anti-
microbial [6], anti-infective [7] and antifungal [8-9] activities.
In our previous work, the multicomponent reactions of
3-amino-1,2,4-triazole with aromatic aldehydes and pyruvic
acid (arylpyruvic acids) were discussed from the viewpoints
of their selectivity and molecular diversity. Different types
of heterocycles depending on the structures of the reagents,
the solvent, the temperature mode, and the activation
method were formed [10-13]. In particular, the
multicomponent approaches based on the reaction of
3-amino-1,2,4-triazole, aromatic aldehydes, and pyruvic
acid were described for the synthesis of
dihydrotriazolopyrimidine-5-carboxylic acids I, 7-hydroxy-
tetrahydropyrimidine-7-carboxilic acid II, benzotriazo-
Received:
Revised:
Accepted:
Published online:
04.11.2020
12.11.2020
19.11.2020
30.12.2020
Corresponding author. Tel.: +380-67-576-6227;
e-mail: chebanov@isc.kh.ua (V. A. Chebanov)
ORCID: 0000-0001-7564-778X
looxadiazocine-5-carboxylic acids III and 3-hydroxy-
triazolyldihydropyrrolones IV (Scheme 1). The reaction
conditions were found for the selective synthesis of each of
these compounds (I-IV). Application of non-classical
activation methods like ultrasonication and microwave
irradiation have appeared as convenient tools for tuning the
multicomponent treatments.
Scheme 1. Diversity of heterocyclizations of 3-amino-1,2,4-
triazole with aldehydes and pyruvic acids.
© Sakhno Ya. 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.
mailto:chebanov@isc.kh.
https://orcid.org/0000-0001-5556-9147
Ya. N. Sakhno, M. V. Mikhailenko, M. A. Kolosov et al.
23
Scheme 2. Switchable heterocyclizations of 3-(methylthio)-1H-1,2,4-triazol-5-amine with aldehydes and pyruvic acids.
Some reactions involving sulfur-containing substituents
in the 3rd position of 3-amino-1,2,4-triazole were described
in the literature as well [14-19].
Results and Discussion
Here, we report the Doebner-type synthesis of
undescribed 2-methylthiotetrahydrotriazolo[1,5-a]pyri-
midine-7-carboxylic acids, and 2-methylthiodihydro-
triazolo[1,5-a]pyrimidine-5-carboxylic acids. The type of
final heterocycle forming in the multicomponent reaction
between 3-(methylthio)-1H-1,2,4-triazol-5-amine, aromatic
aldehydes and pyruvic acid depends on the reaction
conditions – conventional heating or ultrasonication.
In particular, it was found that the three-component
treatment of an equimolar mixture of 3-(methylthio)-1H-
1,2,4-triazol-5-amine (1), aromatic aldehydes 2a-d, and
pyruvic acid (3) under conventional heating at reflux in
glacial acetic acid for 4 hours selectively led to the
formation of a dihydropyrimidine ring and thus
2-(methylthio)-7-aryl-4,7-dihydro-[1,2,4]triazolo[1,5-a]py-
rimidine-5-carboxylic acids 4a-d were isolated as the only
products of the interaction in satisfactory yields (Scheme 2,
Method A, and Table 1).
On the other hand, the multicomponent reaction of the
same starting materials 1, 2a-d, and 3 in glacial acetic acid
under ultrasonication at room temperature for 2 hours led to
the formation of 7-hydroxy-2-(methylthio)-5-aryl-4,5,6,7-
tetrahydro-[1,2,4]triazolo-[1,5-a]pyrimidine-7-carboxylic
acids 5a-d (Scheme 2, Method B, and Table 1). Mechanical
stirring at room temperature instead of ultrasonication led to
the formation of compounds 5a-d as well. However, this
procedure required a longer reaction time (ca. 30 h) and the
yield and purity of the products were significantly lower.
It should be noted, that dihydropyrazolopyrimidine
carboxylic acids 4 were formed by sequential procedure as
well. The linear pathway included two steps: the synthesis
of arylidenpyruvic acids 6a,b starting from appropriate
aromatic aldehyde 2 and pyruvic acid 3, and their further
heterocyclization with 3-(methylthio)-1H-1,2,4-triazol-5-
amine 1 in glacial acetic acid under conventional heating for
30 min gave dihydropyrazolopyrimidine carboxylic acids
4a,b (Scheme 2, Method C). Thus, the final reaction
products 4 were identical to the compounds isolated from
the multicomponent reaction (Scheme 2, Method A) in
similar yields (Table 1).
The structures of the heterocyclic carboxylic acids 4a-d
and 5a-d were established by MS, 1H and 13C NMR spectral
data. The 1H NMR spectra of 2-(methylthio)-7-aryl-4,7-
dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-5-carboxylic acids
4a-d show the following signals: a broad singlet for NH
group (9.82-9.99 ppm), signals of aromatic H-atoms and
terminal groups, a doublet for H-atom in position 7 of the
heterocycle (6.12-6.30 ppm, J = 3.9 Hz), a doublet for
ethylene H-atom at C-5 (5.72-5.77 ppm, J = 3.7 Hz), a
singlet for methyl group (2.38-2.39 ppm). The 1H NMR
spectra of 7-hydroxy-2-(methylthio)-5-aryl-4,5,6,7-tetra-
hydro-[1,2,4]-triazolo[1,5-a]pyrimidine-7-carboxylic acids
5a-d show a broad signal for the pyrimidine NH at δ = 7.78-
7.94 ppm, a singlet for methyl group (2.42-2.43 ppm), a
multiplet for the CH group at C-5 at δ = 4.54-4.80 ppm, a
multiplet for the CH2 group at C-6 at δ = 2.03-2.41 ppm,
and peaks for aromatic protons as well as signals for other
substituents.
The structure of compounds 4a-d and 5a-d was
additionally confirmed by the comparison of their 1H NMR
spectra with literature data for similar pyrimidines [10-12].
MS and 13C NMR are also in an agreement with the
proposed structures.
ISSN 1814-9758. Ukr. Bioorg. Acta, 2020, Vol. 15, N 2
24
Table 1. Synthesis of compounds 4a-d and 5a-d.
Entry Starting materials
Reaction
time
Pathway
Conditions
Product
Yield
Compd. R (hours) Δ or US (%)
1 2a C6H5 4 A Δ 4a 37
2 2b 4-Cl-C6H4 4 A Δ 4b 64
3 2c 4-CH3O-C6H4 4 A Δ 4c 44
4 2d 4-COOCH3-C6H4 4 A Δ 4d 43
5 2a C6H5 2 B US 5a 67
6 2b 4-Cl-C6H4 2 B US 5b 40
7 2c 4-CH3O-C6H4 2 B US 5c 69
8 2d 4-COOCH3-C6H4 2 B US 5d 64
9 6a 4-Cl-C6H4 0.5 C Δ 4b 40
10 6b 4-CH3O-C6H4 0.5 C Δ 4c 43
Conclusions
Thus, we showed that the multicomponent reactions
involving 5-amino-3-methylthio-1,2,4-triazole, aromatic
aldehydes, and pyruvic acid can be switched between two
different pathways using either conventional thermal
heating in acetic acid or ultrasonic activation at room
temperature in the same solvent. Under conventional
heating 2-(methylthio)-7-aryl-4,7-dihydro-[1,2,4]triazolo-
[1,5-a]pyrimidine-5-carboxylic acids were formed both in
the three-component treatment and in sequential two-step
reaction via preliminary synthesis of arylidenpyruvic acid.
In the case of ultrasonic activation the multicomponent
reaction led to the formation of 7-hydroxy-2-(methylthio)-
5-aryl-4,5,6,7-tetrahydro-[1,2,4]triazolo-[1,5-a]pyrimidine-
7-carboxylic acids.
Experimental section
Melting points were determined with a Kofler apparatus
and were uncorrected. The 1H and 13C NMR spectra were
recorded in DMSO-d6 at 400 MHz (100 MHz for 13C NMR)
with a Varian MR-400 spectrometer.
The mass spectra were measured Shimadzu GCMS-2020
instrument (70 eV ionizing energy) using the direct inlet
(DI) method. Elemental analysis was performed on a Euro
Vector EA-3000.
Ultrasound-assisted experiments were carried out using a
standard ultrasound bath (SELDI, Ukraine) with a working
frequency of 44.2 kHz.
Arylidenpyruvic acids 4a-b were synthesized according
to the literature procedure [20]. 3-(Methylthio)-1H-1,2,4-
triazol-5-amine (1), 2-oxopropa-noic acid 2, and substituted
aldehydes 3a-d were commercially available and were
purchased from Merck.
General procedure for the preparation of compounds
5a-d:
Method A: 100 mg (0.77 mmol) of 3-(methylthio)-1H-
1,2,4-triazol-5-amine (1) were dissolved in glacial AcOH
(2 mL), then pyruvic acid (2; 0.77 mmol) and the
appropriate aldehyde (2a-2d; 0.77 mmol) were added. The
mixture was refluxed for 4h, then it was cooled and allowed
to stand overnight. After that, the resulting precipitate was
collected by filtration and dried in air, yielding a colorless
solid.
2-(methylthio)-7-phenyl-4,7-dihydro[1,2,4]triazolo-[1,5-
a]pyrimidine-5-carboxylic acid (4a):
Yield: 27 mg, 37%; Colorless solid; mp 259-261 °C.
1H NMR (400 MHz, DMSO-d6) δ 9.86 (s, 1H, NH), 7.15-
7.42 (m, 5H, ArH), 6.18 (d, J 3.9 Hz, 1H), 5.77 (d, J 3.7 Hz,
1H), 2.39 (s, 3H, SCH3). Anal. Calcd. for C13H12N4O2S: C,
54.16; H, 4.20; N, 19.43. Found C, 54.08; H, 4.27; N,
19.51. MS (EI, 70 eV) m/z (%) 288 (M+, 100), 243 (30),
211 (61), 193 (45), 165 (27), 115 (50), 77 (39).
7-(4-chlorophenyl)-2-(methylthio)-4,7-dihydro-[1,2,4]
triazolo[1,5-a]pyrimidine-5-carboxylic acid (4b):
Yield: 76 mg, 64%; Colorless solid; mp 285-287 °C.
1H NMR (400 MHz, DMSO-d6) δ 9.89 (s, 1H, NH), 7.20-
7.46 (m, 4H, ArH), 6.22 (d, J 3.9 Hz, 1H, CH), 5.76 (d,
J 3.7 Hz, 1H, CH), 2.39 (s, 3H, SCH3). 13C NMR
(100 MHz, DMSO-d6) δ 163.7; 159.9; 150.6; 140.6; 133.9;
129.8; 129.7; 128.5; 106.9; 59.6; 14.4. Anal. Calcd. for
C13H11ClN4O2S: C, 48.38; H, 3.44; N, 17.36. Found C,
48.25; H, 3.47; N, 17.39. MS (EI, 70 eV) m/z (%) 322 (M+,
30), 290 (11), 286 (18), 241 (18), 211 (65), 193 (56), 165
(52), 140 (60).
7-(4-methoxyphenyl)-2-(methylthio)-4,7-dihydro-[1,2,4]
triazolo[1,5-a]pyrimidine-5-carboxylic acid (4с):
Yield: 106 mg, 44%; Colorless solid; mp 273-275 °C.
1H NMR (400 MHz, DMSO-d6) δ 9.82 (s, 1H, NH), 6.87-
Ya. N. Sakhno, M. V. Mikhailenko, M. A. Kolosov et al.
25
7.18 (m, 4H, ArH), 6.12 (d, J 3.9 Hz, 1H, CH), 5.75 (d,
J 3.7 Hz, 1H, CH), 3.73 (s, 3H, OCH3), 2.39 (s, 3H, SCH3).
Anal. Calcd. for C14H14N4O3S: C, 52.82; H, 4.43; N, 17.60.
Found C, 52.72; H, 4.51; N, 17.65. MS (EI, 70 eV) m/z (%)
318 (M+, 89), 271 (65), 211 (34), 193 (40), 158 (100), 145
(72), 128 (50).
7-(4-(methoxycarbonyl)phenyl)-2-(methylthio)-4,7-di-
hydro[1,2,4]triazolo[1,5-a]pyrimidine-5-carboxylic acid
(4d):
Yield: 120 mg, 43%; Colorless solid; mp 255-257 °C.
1H NMR (400 MHz, DMSO-d6) δ 9.99 (s, 1H, NH), 7.32-
8.02 (m, 4H, ArH), 6.30 (d, J 3.9 Hz, 1H, CH), 5.78 (d,
J 3.7 Hz, 1H, CH), 3.84 (s, 3H, OCH3), 2.38 (s, 3H, SCH3).
13C NMR (100 MHz, DMSO-d6) δ 165.9; 162.7; 159.0;
149.8; 145.6; 129.8; 129.5; 127.6; 127.1; 105.8; 59.1; 52.2;
13.5. Anal. Calcd. for C15H14N4O4S: C, 52.02; H, 4.07; N,
16.18. Found C, 51.96; H, 4.16; N, 16.25. MS (EI, 70 eV)
m/z (%) 346 (M+, 1), 211 (28), 165 (36), 140 (40), 128 (36),
119 (45), 115 (77).
The same compounds as 4b and 4c were obtained via
two-component reaction (Method C) including appropriate
arylidenpyruvic acids 6a-b and 3-(methylthio)-1H-1,2,4-
triazol-5-amine (1). 100 mg (0.77 mmol) of 3-(methylthio)-
1H-1,2,4-triazol-5-amine (1) were dissolved in glacial
AcOH (2 mL), then appropriate 2-oxo-4-arylbut-3-enoic
acids were added. The mixture was refluxed for 30 min,
then it was cooled and allowed to stand overnight. After
that, the resulting precipitate was collected by filtration and
dried in air, yielding a colorless solid.
Method B: 100 mg (0.77 mmol) of 3-(methylthio)-1H-
1,2,4-triazol-5-amine (1) were dissolved in glacial AcOH
(2 mL), then the appropriate aldehyde (2a-d; 0.77 mmol)
and pyruvic acid (3; 0.77 mmol) were added. The mixture
was put into the ultrasound bath for 120 min. Then the
mixture was allowed to stand overnight. After that, the
resulting precipitate was collected by filtration and dried in
air, yielding a colorless solid.
7-hydroxy-2-(methylthio)-5-phenyl-4,5,6,7-tetrahydro-
[1,2,4]triazolo[1,5-a]pyrimidine-7-carboxylic acid (5a):
Yield: 160 mg, 67%; Colorless solid; mp 152-154 °C.
1H NMR (400 MHz, DMSO-d6); δ 7.84 (s, 1H, NH), 7.26-
7.66 (m, 5H, ArH), 4.57-4.70 (m, 1H, CH), 2.42 (s, 3H,
SCH3), 2.04-2.32 (m, 2H, CH2). Anal. Calcd. for
C13H14N4O3S: C, 50.97; H, 4.61; N, 18.29. Found C, 50.87;
H, 4.66; N, 18.32. MS (EI, 70 eV) m/z (%) 288 (M+·–H2O,
8), 243 (15), 211 (18), 130 (100).
5-(4-chlorophenyl)-7-hydroxy-2-(methylthio)-4,5,6,7-
tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidine-7-carboxylic
acid (5b):
Yield: 115 mg, 40%; Colorless solid; mp 169-171 °C.
1H NMR (400 MHz, DMSO-d6) δ 7.79 (s, 1H, NH), 6.89-
7.51 (m, 4H, ArH), 4.59-4.70 (m, 1H, CH), 3.06 (s, 3H,
O-CH3), 2.42 (s, 3H, SCH3), 2.04-2.32 (m, 2H, CH2).
13C NMR (100 MHz, DMSO-d6) δ 170.6; 159.4; 155.4;
133.1; 128.2; 114.4; 81.6; 55.6; 50.8; 42.4; 13.9. Anal.
Calcd.. for C13H13ClN4O3S: C, 45.82; H, 3.85; N, 16.44.
Found C, 45.76; H, 3.91; N, 16.52. MS (EI, 70 eV) m/z (%)
322 (M+·–H2O, 3), 211 (6), 165 (87), 137 (46), 130 (79).
7-hydroxy-5-(4-methoxyphenyl)-2-(methylthio)-4,5,6,7-
tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidine-7-carboxylic
acid (5c):
Yield: 180 mg, 69%; Colorless solid; mp 168-170 °C.
1H NMR (400 MHz, DMSO-d6) δ 7.79 (s, 1H, NH), 6.88-
7.41 (m, 4H, Ar), 4.54-4.63 (m, 1H, CH), 3.75 (s, 3H,
OCH3), 2.42 (s, 3H, SCH3), 2.03-2.31 (m, 2H, CH2).
Anal. Calcd. for C14H16N4O4S: C, 49.99; H, 4.79; N, 16.66.
Found: C, 50.07; H, 4.76; N, 16.71. MS (EI, 70 eV)
m/z (%) 318 (M+ –H2O, 20), 271 (21), 151 (100), 133 (52),
130 (61).
7-hydroxy-5-(4-(methoxycarbonyl)phenyl)-2-(methyl-
thio)-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidine-7-
carboxylic acid (5d):
Yield: 179 mg, 64%; Colorless solid; mp 159-161 °C.
1H NMR (400 MHz, DMSO-d6) δ 7.74 (s, 1H, NH), 7.46-
8.20 (m, 4H, Ar), 4.68-4.80 (m, 1H, CH), 3.90 (s, 3H,
OCH3), 2.43 (s, 3H, SCH3), 2.13-2.41 (m, 2H, CH2).
Anal. Calcd. for C15H16N4O5S: C, 49.44; H, 4.43; N, 15.38.
Found: C, 49.36; H, 4.51; N, 15.41. MS (EI, 70 eV)
m/z (%) 346 (M+·–H2O, 3), 189 (67), 145 (40), 130 (100).
Notes
Acknowledgments and finances. The authors thank the
National Academy of Sciences of Ukraine for financial
support in the frame of the projects "Creation of modern
bases for obtaining and analyzing substances and
components of materials for pharmaceutical purposes"
(0119U100727) and "Functional materials for biomedical
purposes based on halogen-containing organic compounds"
(0120U102660).
The authors declare no conflict of interest.
Author contributions. Ya. I. S.: synthesis of
compounds, investigation, formal analysis, writing of the
most part of the manuscript, editing. M. V. М.: synthesis of
compounds, writing experimental section of the manuscript,
formal analysis. N. V. C.: experimental section. M. A. K.
and E. H. S.: mass experiments. S. M. D.: editing. M. V. I.:
NMR correlation experiments. V. A. C. conceptualization,
supervision, writing - review & editing.
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Переключаємі за рахунок умов багатокомпонентні реакції
5-аміно-3-(метилтіо)-1,2,4-триазолу, ароматичних альдегідів
та піровиноградної кислоти
Я. І. Сахно1, М. В. Михайленко1,2, М. О. Колосов2, О. Г. Швець2, В. I. Мусатов1, Н. В. Чорна1,
С. М. Десенко1, В. А. Чебанов1,2*
1 Науково-технологічний комплекс «Інститут монокристалів» НАН України, пр. Науки, 60, Харків, 61072, Україна
2 Харківський національний університет імені В. Н. Каразіна, пл. Свободи, 4, Харків, 61077, Україна
Резюме: Вивчено багатокомпонентні реакції 5-аміно-3-метилтіо-1,2,4-триазолу з ароматичними альдегідами та піровиноградною кислотою із
застосуванням звичайного термічного нагріву та при використанні ультразвукової активації при кімнатній температурі у тому ж самому
розчиннику. При звичайному нагріванні в оцтовій кислоті утворювались 2-(метилтіо)-7-арил-4,7-дигідро-[1,2,4]триазоло-[1,5-а]піримідин-5-
карбонові кислоти, як при трикомпонентній реакції, так і при послідовній двохкомпонентній реакції, шляхом попереднього синтезу
ариліденпіровиноградних кислот. У випадку ультразвукової активації багатокомпонентна реакція в оцтовій кислоті за кімнатної температури
приводила до утворення 7-гідрокси-2-(метилтіо)-5-арил-4,5,6,7-тетрагідро-[1,2,4]триазоло-[1,5-а]піримідин-7-карбонових кислот. Подальше
вивчення особливостей утворення даних речовин має суттєве фундаментальне значення для детального розуміння механізмів формува ння
азолоазинових систем, що є важливим для цілеспрямованого синтезу гетероциклічних систем, які мають заздалегідь задані властивості. Показано
перспективність синтезу нових гетероциклічних сполук цього класу, які прогнозовано мають широкий спектр біологічної активності.
Ключові слова: 5-аміно-3-(метилтіо)-1,2,4-триазол; багатокомпонентна реакція; ультразвук; піровиноградна кислота; гетероциклізація.
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| id | oai:ojs2.bioorganica.com.ua:article-37 |
| institution | Ukrainica Bioorganica Acta |
| keywords_txt_mv | keywords |
| language | English |
| last_indexed | 2026-07-20T01:00:50Z |
| publishDate | 2020 |
| 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/c3/92ae66da4b6d3e1172b0449162a2e1c3.pdf |
| spelling | oai:ojs2.bioorganica.com.ua:article-372026-07-19T14:56:53Z Condition-based switching the multicomponent reactions of 5-amino-3-(methylthio)-1,2,4-triazole, aromatic aldehydes, and pyruvic acid Переключаємі за рахунок умов багатокомпонентні реакції 5-аміно-3-(метилтіо)-1,2,4-триазолу, ароматичних альдегідів та піровиноградної кислоти Sakhno, Yana I. Mykhailenko, Maksym V. Kolosov, Maksim A. Shvets, Elena H. Musatov, Vladimir I. Chorna, Natalia V. Desenko, Sergey M. Chebanov, Valentyn A. 5-аmino-3-(methylthio)-1,2,4-triazole multicomponent reaction ultrasonication pyruvic acid heterocyclization 5-аміно-3-(метилтіо)-1,2,4-триазол багатокомпонентна реакція ультразвук піровиноградна кислота гетероциклізація The multicomponent reactions of 5-amino-3-methylthio-1,2,4-triazole with aromatic aldehydes and pyruvic acid were studied using conventional thermal heating and ultrasonic activation at room temperature. Under conventional heating, dihydrotriazolopyrimidine derivatives were formed in both two- and three-component treatments. In the case of ultrasonic activation, the multicomponent reaction led to the formation of 7-hydroxytetrahydrotriazolopyrimidines Вивчено багатокомпонентні реакції 5-аміно-3-метилтіо-1,2,4-триазолу з ароматичними альдегідами та піровиноградною кислотою із застосуванням звичайного термічного нагріву та при використанні ультразвукової активації при кімнатній температурі у тому ж самому розчиннику. При звичайному нагріванні в оцтовій кислоті утворювались 2-(метилтіо)-7-арил-4,7-дигідро-[1,2,4]триазоло-[1,5-а]піримідин-5-карбонові кислоти, як при трикомпонентній реакції, так і при послідовній двохкомпонентній реакції, шляхом попереднього синтезу ариліденпіровиноградних кислот. У випадку ультразвукової активації багатокомпонентна реакція в оцтовій кислоті за кімнатної температури приводила до утворення 7-гідрокси-2-(метилтіо)-5-арил-4,5,6,7-тетрагідро-[1,2,4]триазоло-[1,5-а]піримідин-7-карбонових кислот. Подальше вивчення особливостей утворення даних речовин має суттєве фундаментальне значення для детального розуміння механізмів формування азолоазинових систем, що є важливим для цілеспрямованого синтезу гетероциклічних систем, які мають заздалегідь задані властивості. Показано перспективність синтезу нових гетероциклічних сполук цього класу, які прогнозовано мають широкий спектр біологічної активності V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine 2020-12-30 Article Article application/pdf https://bioorganica.com.ua/index.php/journal/article/view/37 10.15407/bioorganica2020.02.022 Ukrainica Bioorganica Acta; Vol. 15 No. 2 (2020): Ukrainica Bioorganica Acta; 22-26 Ukrainica Bioorganica Acta; Том 15 № 2 (2020): Ukrainica Bioorganica Acta; 22-26 1814-9766 1814-9758 10.15407/bioorganica2020.02 en https://bioorganica.com.ua/index.php/journal/article/view/37/36 Copyright (c) 2020 Yana I. Sakhno, Maksym V. Mykhailenko, Maksim A. Kolosov, Elena H. Shvets, Vladimir I. Musatov, Natalia V. Chorna, Sergey M. Desenko, Valentyn A. Chebanov https://creativecommons.org/licenses/by/4.0 |
| spellingShingle | 5-аміно-3-(метилтіо)-1,2,4-триазол багатокомпонентна реакція ультразвук піровиноградна кислота гетероциклізація Sakhno, Yana I. Mykhailenko, Maksym V. Kolosov, Maksim A. Shvets, Elena H. Musatov, Vladimir I. Chorna, Natalia V. Desenko, Sergey M. Chebanov, Valentyn A. Переключаємі за рахунок умов багатокомпонентні реакції 5-аміно-3-(метилтіо)-1,2,4-триазолу, ароматичних альдегідів та піровиноградної кислоти |
| title | Переключаємі за рахунок умов багатокомпонентні реакції 5-аміно-3-(метилтіо)-1,2,4-триазолу, ароматичних альдегідів та піровиноградної кислоти |
| title_alt | Condition-based switching the multicomponent reactions of 5-amino-3-(methylthio)-1,2,4-triazole, aromatic aldehydes, and pyruvic acid |
| title_full | Переключаємі за рахунок умов багатокомпонентні реакції 5-аміно-3-(метилтіо)-1,2,4-триазолу, ароматичних альдегідів та піровиноградної кислоти |
| title_fullStr | Переключаємі за рахунок умов багатокомпонентні реакції 5-аміно-3-(метилтіо)-1,2,4-триазолу, ароматичних альдегідів та піровиноградної кислоти |
| title_full_unstemmed | Переключаємі за рахунок умов багатокомпонентні реакції 5-аміно-3-(метилтіо)-1,2,4-триазолу, ароматичних альдегідів та піровиноградної кислоти |
| title_short | Переключаємі за рахунок умов багатокомпонентні реакції 5-аміно-3-(метилтіо)-1,2,4-триазолу, ароматичних альдегідів та піровиноградної кислоти |
| title_sort | переключаємі за рахунок умов багатокомпонентні реакції 5-аміно-3-(метилтіо)-1,2,4-триазолу, ароматичних альдегідів та піровиноградної кислоти |
| topic | 5-аміно-3-(метилтіо)-1,2,4-триазол багатокомпонентна реакція ультразвук піровиноградна кислота гетероциклізація |
| topic_facet | 5-аmino-3-(methylthio)-1,2,4-triazole multicomponent reaction ultrasonication pyruvic acid heterocyclization 5-аміно-3-(метилтіо)-1,2,4-триазол багатокомпонентна реакція ультразвук піровиноградна кислота гетероциклізація |
| url | https://bioorganica.com.ua/index.php/journal/article/view/37 |
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