Chemistry of Heterocyclic Compounds

, Volume 41, Issue 9, pp 1139-1146

First online:

Acyl and Sulfonyl Derivatives of 3,5-Diamino-1-R-1,2,4-triazoles

  • V. M. ChernyshevAffiliated withSouth-Russian State Technical University
  • , V. A. RakitovAffiliated withSouth-Russian State Technical University
  • , V. A. TaranushichAffiliated withSouth-Russian State Technical University
  • , V. V. BlinovAffiliated withSouth-Russian State Technical University

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3-Acylamino-5-amino-1-R-1,2,4-triazoles are formed regioselectively on acylating 3,5-diamino-1-R-1,2,4-triazoles with an equimolar amount of anhydrides, carboxylic acid chlorides, and sulfonyl chlorides. With an excess of anhydride and carboxylic acid chloride 3,5-diacylamino-1-R-1,2,4-triazoles are formed. 3-Acylamino-5-amino-1-R-1,2,4-triazoles do not interact with sulfonyl chlorides. The higher reactivity of the 3-amino group towards acylating agents is determined by electronic and not steric factors.


3-acylamino-5-amino-1-R-1,2,4-triazoles 5-amino-3-sulfonylamino-1-R-1,2,4-triazoles amino- 3,5-diamino-1,2,4-triazole 3,5-diacylamino-1,2,4-triazoles 1,2,4-triazole acylation regioselectivity structure