METHYLATION AND AMINATION OF 4 H -[1,2,3]TRIAZOLO[4,5- c ][1,2,5]OXADIAZOLE SALTS

S. P. Balabanova; Балабанова С. П.; A. A. Voronin; Воронин А. А.; A. M. Churakov; Чураков А. М.; M. S. Klenov; Кленов М. С.; V. A. Tartakovsky; Тартаковский В. А.

doi:10.31857/S2686953522600805

METHYLATION AND AMINATION OF 4H-[1,2,3]TRIAZOLO[4,5-c][1,2,5]OXADIAZOLE SALTS

Authors: Balabanova S.P.¹, Voronin A.A.¹, Churakov A.M.¹, Klenov M.S.¹, Tartakovsky V.A.¹
Affiliations:
1. N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Issue: Vol 512, No 1 (2023)
Pages: 83-87
Section: CHEMISTRY
URL: https://rjmseer.com/2686-9535/article/view/651955
DOI: https://doi.org/10.31857/S2686953522600805
EDN: https://elibrary.ru/ZGDGAZ
ID: 651955

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Abstract

The methylation and the amination of 4H-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazole salts (K⁺, Ag⁺, Et₃NH⁺, DBUH⁺) were studied for the first time. It is shown that two methylated products are formed in the reaction. In the case of K- and Et₃N-salts, 4- and 5-methylated isomers are formed in equal proportions, and in the case of Ag- and DBU-salts, the main product is the 4-isomer. It was found that the main product of amination of both 4H-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazole K- and DBU-salts with O-(p-tolylsulfonyl)hydroxylamine is 4-azido-3-amino-1,2,5-oxadiazole. The mechanism of its formation as a result of rearrangement of 5-amino-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazole is proposed.

Keywords

1,2,3-triazole, 1,2,5-oxadiazole, amination, methylation

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