Abstract
New pyrazolo[1,5-a][1,3,5]triazines with a heteroaromatic substituent in position 4 and dichloromethyl moiety in position 2 were obtained via a heterocyclization reaction of readily available reagents - N-(2,2-dichloro-1-cyanoethenyl)carboxamides and 3(5)-aminopyrazoles. The high efficiency of the proposed method for the synthesis of 2-(dichloromethyl)-pyrazolo[1,5-a][1,3,5]triazines with furan-2-yl, thien-2-yl, and pyridine-3-yl substituents was demonstrated.
References
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2. Li Y.W., Fitzgerald L., Wong H., Lelas S., Zhang G., Lindner M.D., Wallace T., McElroy J., Lodge N.J., Gilligan P., Zaczek R. The pharmacology of DMP696 and DMP904, non-peptidergic CRF1 receptor antagonists. CNS Drug Review. 2005. 11 (1): 21.
3. Lubbers T., Angehrn P., Gmunder H., Herzig S., Kulhanek J. Design, synthesis, and structure-activity relationship studies of ATP analogues as DNA gyrase inhibitors. Bioorganic & Medicinal Chemistry Letters, 2000. 10 (8): 821.
4. Robins R. K., Revankar G. R., O’Brien D. E., Springer R. H., Novinson T., Albert A., Senga K., Miller J. P., Streeter D. G. Purine analog inhibitors of xanthine oxidase – structure activity relationships and proposed binding of the molybdenum cofactor. Journal of Heterocyclic Chemis-try. 1985. 22 (3): 601.
5. Shaabani A., Nazeri M.T., Afshari R. 5-Amino-pyrazoles: potent reagents in organic and medicinal synthesis. Molecular Di-versity. 2018. 22 (1): 1.
6. Matsumura K., Saraie T., Hashimoto N. ββ-Dichloro-α-aminoacrylonitrile. Journal of the Chemical Society, Chemical Com-munications. 1972. 1 (12): 705.
7. Velihina Ye.S., Pil'o S.G., Zyabrev V.S., Brovarets V.S. Synthesis and antiviral ac-tivity of 2-(dichloromethyl)pyrazolo[1,5-a][1,3,5]-triazines. Dopovidi Nacional'noi akademii nauk Ukrainy. 2019. (7): 75.
8. Demidchuk B.A., Brovarets V.S., Chernega A.N., Howard J.A.K., Vasilenko A.N., Turov A.V., Drach B.S. Reaction of 1-Aryl-1,3,4,4-tetrachloro-2-azabuta-1,3-dienes with amino-azoles. Russian Journal of General Chemistry (Engl. Transl.). 2007. 77 (3): 474.
9. Velihina Velihina, Y. S., Zyabrev, V. S., Moskvina, V. S., Shablykina, O. V., & Brovarets, V. S. 2-(Dichloromethyl) pyrazolo [1, 5-a][1, 3, 5] triazines: synthesis and anticancer activity. Biopolymers and Cell. 2020. 36(1): 60-73.
10. Drach B.S., Sviridov E.P., Lavrenyk T.Y. Reaction of α-acylamino-β,β-dichloroacrylo-nitriles with primary amines. Journal of Organic Chemistry USSR (Engl. Transl.). 1974. 10 (6): 1278.
11. Drach B.S., Sviridov E.P., Kisilenko A.A., Kirsanov A.V. Interaction of secondary amines with N-acyl-2,2-dichlorovinylamines and N-acyl-1-cyano-2,2-dichlorovinylamines. Journal of organic chemistry of the USSR: transl. from Russian. 1973. 9 (9): 1842.
12. Pianka M., Edwards J.D., Smith C.B. Stud-ies in fungitoxicity. V.—Fungicidal activity of certain dithiocarbamates. Journal of the Science of Food and Agriculture. 1966. 17 (9): 407.
13. Meyer A.E. Chloral nicotinamide and method for preparing the same. US2721203. 1953.
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