Methylation and Amination of 4H-[1,2,3]Triazolo[4,5-c][1,2,5]oxadiazole Salts

Methylation and Amination of 4H-[1,2,3]Triazolo[4,5-c][1,2,5]oxadiazole Salts Full article

Journal

Doklady Chemistry
ISSN: 1608-3113 , E-ISSN: 0012-5008

Output data

Year: 2023, Volume: 512, Number: 2, Pages: 288-291 Pages count : 4 DOI: 10.1134/s0012500823600669

Authors

Balabanova S.P. ¹ , Voronin A.A. ¹ , Churakov A.M. ¹ , Klenov M.S. ¹ , Tartakovsky V.A. ¹

Affiliations

1	Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russia

Methylation and amination reactions of 4Н-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazole salts (K+, Ag+, Et3NH+, DBUH+) have been studied for the first time. It has been shown that the reaction of these salts with MeI results in two methylation products: K and Et3N salts produce 4- and 5-isomers in equal amounts, while Ag and DBU salts form mainly 4-isomer. It has been found that the main amination product of K and DBU salts of 4Н-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazole with O-(p-tolylsulfonyl)hydroxylamine is 4-azido-3-amino-1,2,5-oxadiazole. A mechanism of its formation via rearrangement of 5-amino-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazole has been proposed.

Balabanova S.P. , Voronin A.A. , Churakov A.M. , Klenov M.S. , Tartakovsky V.A.
Methylation and Amination of 4H-[1,2,3]Triazolo[4,5-c][1,2,5]oxadiazole Salts
Doklady Chemistry. 2023. V.512. N2. P.288-291. DOI: 10.1134/s0012500823600669 WOS Scopus OpenAlex

≡ Web of science:	WOS:001130184300008
≡ Scopus:	2-s2.0-85180661546
≡ OpenAlex:	W4390191026