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AN UNEXPECTED DIRECTION OF THE REACTION OF HYDRAZINO-1,3,5-TRIAZINES WITH FORMIC ACID. SYNTHESIS OF (4H-1,2,4-TRIAZOL-3-YL)GUANIDINES

Владимир В. Бахарев, Виктор Е. Парфенов, Ирина В. Ульянкина, Анна В. Заводская, Александр А. Гидаспов, Павел А. Слепухин
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Abstract


A new direction of the reaction of 6-amino-substituted 4-hydrazino-1,3,5-triazin-2(1H)-ones with formic acid was found leading to the formation of N-substituted (4H-1,2,4-triazol-3-yl)guanidines together with the expected 5-amino-substituted 1,2,4-triazolo[1,5-a][1,3,5]triazin-7-ones as a result of opening of the triazine ring and subsequent decarboxylation of an intermediate of the Dimroth rearrangement. The discovered reaction is of interest as a novel method for the synthesis of N-substituted (4H-1,2,4-triazol-3-yl)guanidines.

How to Cite
Bakharev, V. V.; Parfenov, V. E.; Ul'yankina, I. V.; Zavodskaya, A. V.; Gidaspov, A. A.; Slepukhin, P. A. Chem. Heterocycl. Compd. 2015, 51, 1014. [Khim. Geterotsikl. Soedin. 2015, 51, 1014.]

For this article in the English edition see DOI 10.1007/s10593-016-1812-z

 


Keywords


nitrogen heterocycles; 1,2,4-triazolylguanidines; 1,2,4-triazolo[1,5-a][1,3,5]triazin-7-ones; Dimroth rearrangement; 1,3,5-triazine ring opening

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