Alternative Approach to 1,2,4-Triazole-3-carboxamides

Abstract

The conversion of trichloromethyl and tribromomethyltriazoles to the corresponding carboxamide derivatives is described. The trihalomethyl analogs are straightforward to make and react readily with a range of amines to produce carboxamides. The strategy avoids the problems of decarboxylation associated with the use of triazole acids.

Keywords:

• 1,2,4-Triazole carboxamides
• triazole carboxylic acids
• trihalomethyloxadiazoles

Acknowledgments

This paper is dedicated to the memory of Olga Wallace, a fine young chemist.

Notes

^a Ee of compound 7 is 95.4% (rt 12.9 min).

^b Ee of compound 8 is 94% (rt 17.1 min). Determined on Chiralpak IA column with Heptane/IPA as eluent. This indicates that the chiral integrity has been maintained for these amines.