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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 14
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Original Articles

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

Pages 2585-2595 | Received 20 Aug 2008, Published online: 16 Jun 2009
 

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.

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.

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