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- Title
Alkylation of acyl and sulfonyl derivatives of 3,5-diamino-1-phenyl-1,2,4-triazole.
- Authors
Chernyshev, V. M.; Rakitov, V. A.; Blinov, V.; Taranushich, V. V.; Starikova, Z. A.
- Abstract
Alkylation of 3-acylamino-, 5-amino-1-phenyl-3-tosylamino-1,2,4-triazoles and 3,5-diacetylamino-1-phenyl-1,2,4-triazole in the presence of an equimolar amount of sodium methylate in DMSO occurs regioselectively at the amide (sulfamide) group nitrogen atom. The benzylation of 3-acetylamino-5-amino-1-phenyl-1,2,4-triazole with excess base and benzyl chloride also alkylates the amino group at position 5. Alkylamino-1-R-1,2,4-triazoles can be conveniently prepared by alkylation of the corresponding acetylamino-1,2,4-triazoles in the presence of base and subsequent acid hydrolysis of the N-acetyl-N-alkyl derivatives.
- Subjects
CHEMICAL reactions; HYDROCARBONS; AZOLES; ORGANOSODIUM compounds; NITROSAMIDES
- Publication
Chemistry of Heterocyclic Compounds, 2009, Vol 45, Issue 4, p436
- ISSN
0009-3122
- Publication type
Article
- DOI
10.1007/s10593-009-0290-y