5,6-Dihydro-[1,2,4]triazolo[1,5-c]quinazolines. Message 1. Features of interactions between [2-(3-aryl-1H-1,2,4-triazole-5-yl)phenyl]amines, aliphatic and aromatic aldehydes

S. V. Kholodnyak, K. P. Schabelnyk, O. Yu. Voskoboynik, G. G. Berest, S. I. Kovalenko


Reactions of [5+1]-cyclocondensation of [2-(3-aryl-1H-1,2,4-triazol-5-yl)phenyl]amines with aliphatic and aromatic aldehydes produce the corresponding 5-R-2-aryl-5,6-dihydro- or 5-R-2-aryl-[1,2,4]triazolo[1,5-с]quinazolines depending on the conditions. The optimal conditions of the reaction have been found, and factors contributing to oxidation of 5-R-2-aryl-5,6-dihydro-[1,2,4]triazolo[1,5-с]quinazolines have been determined. The alternative synthetic approaches for 5-R-2-aryl-[1,2,4]triazolo[1,5-с]quinazolines, namely oxidation of their reduced analogues and interaction of [2-(3-aryl-1H-1,2,4-triazol-5-yl)phenyl]amines with acylhalides of aliphatic or aromatic carboxylic acid have been proposed. Purity and the structure of the compounds synthesized have been confirmed by the complex of physicochemical methods, including LC-MS, 1H-, 13C NMR, mass-spectrometry and elemental analysis. The peculiarities and differences of 1H- and 13C-NMR spectral patterns of 5-R-2-aryl-5,6-dihydro-[1,2,4]triazolo[1,5-c]quinazolines and their aromatic analogues have been described.


5-[2-(3-aryl-1H-1,2,4-triazol-5-yl)phenyl]amines; [5+1]cyclocondensation; spectral characteristics

Full Text:



Khan I., Ibrar A., Abbas N., Saeed A. European Journal of Medicinal Chemistry, 2013, Vol. 76, pp.193-244 doi: 10.1016/j.ejmech.2014.02.005.

Wang D., Gao F. Chemistry Central Journal, 2013, Vol. 7, p.95. doi:10.1186/1752-153X-7-95.

Bilyi A. K., Antypenko L. M., Ivchuk V. V., Kamyshnyi O. M., Polishchuk N. M., Kovalenko S. I. Chem. Plus Chem., 2015, Vol. 6, pp.980-989. doi:10.1002/ cplu.201500051.

Antipenko L. N., Karpenko A. V., Kovalenko S. I., Katsev A. M., Komarovska-Porokhnyavets E. Z., Novikov V. P., 2009, Vol. 342 (11), pp.651-662. doi:10.1002/ardp.200900077.

Špirková K., Stankovský Š., Dandárová M. Collection of Czechoslovak Chemical Communications, 1994, Vol. 59 (1), pp.222-226. doi:10.1135/cccc19940222.

Korshak V. V., Rusanov A. L., Iremashvili Ts G., Zhuravleva I. V., Baranov E. L. Macromolecules, 1973, Vol. 6 (4), pp.483-492. doi:10.1021/ma60034a002.

Gusev A. N., Shul’gin V. F., Topilova Z. M., Meshkova S. B. Russian Chemical Bulletin, Vol. 61 (1), pp.95-98. doi:10.1007/s11172-012-0014-9.

Karpenko A.V., Kovalenko S. I., Shishkina S. V., Shishkin O. V. Chemical Monthly, 2006, Vol. 137 (12), pp.1543-1549. doi:10.1007/s00706-006-0545-6.

Borioni A., Del Giudice M. R., Ferretti R., Mustazza C., Rodomonte A., Sbraccia M., Sestili I. Chemical and Pharmaceutical Bulletin; 2006, Vol. 54 (5), pp.611-622. doi:10.1248/cpb.54.611.

Kovalenko S. I., Antypenko L. M., Bilyi A. K., Kholodnyak S. V., Karpenko O. V., Antypenko O. M. et al. Scientia Pharmaceutica, 2013, Vol. 81 (2), pp.359-391. doi:10.3797/scipharm.1211-08.

Kovalenko S. I, Voloshina V. O., Karpenko O. V. Zhurnal Organichnoi ta Farmatsevtichnoi Khimii – Journal of Organic and Pharmaceutical, 2010, Vol. 8 (2(80)), pp.48-56.

Gunther H. NMR Spectroscopy: Basic Principles, Concepts and Applications in Chemistry, 3rd Edition., Wiley, 2013, 734 p.

GOST Style Citations

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.

Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)