ALKYLATION OF ACYL AND SULFONYL DERIVATIVES OF 3,5-DIAMINO-1-PHENYL-1,2,4-TRIAZOLE

Authors

  • В. М. Чернышев South-Russian State Technical University, Novocherkassk 346428
  • В. А. Ракитов South-Russian State Technical University, Novocherkassk 346428
  • В. В. Блинов South-Russian State Technical University, Novocherkassk 346428
  • В. А. Таранушич South-Russian State Technical University, Novocherkassk 346428
  • З. А. Старикова A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow 117813

DOI:

https://doi.org/10.1007/6751

Keywords:

5-amino-3-(N-acyl-N-alkyl)amino-1-phenyl-1, 2, 4-triazoles, 5-amino-3-(N-alkyl-N-tosyl)-amino-1-phenyl-1, acylamino-1, 3, 5-di(N-acetyl-N-methylamino)-1-phenyl-1, 4-triazole, sulfonylamino-1, alkylation, regioselectivity, X-ray structural analysis, structure

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.

How to Cite
Chernyshev, V. M.; Rakitov, V. A.; Blinov, V. V.; Taranushich, V. A.; Starikova, Z. A.  Chem. Heterocycl. Compd. 2009, 45, 436. [Khim. Geterotsikl. Soedin. 2009, 557.]

For this article in the English edition see DOI 10.1007/s10593-009-0290-y


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Published

2022-04-22

Issue

No. 4 (2009)

Section

Original Papers