Synthesis, structure, and biological activity of 2,6-diazido-4-methylnicotinonitrile derivatives

Abstract

A number of 2,6-diazido-4-methylnicotinonitrile derivatives has been synthesized as prospective novel plant growth regulators. The 2-[(triphenylphosphoranylidene)amino]tetrazolo[1,5-a]pyridine derivative is selectively formed from 2,6-diazido-4-methylnicotinonitrile under the conditions of the Staudinger reaction, from which N-(6-azido-5-cyano-4-methylpyridin-2-yl)acylamides can be obtained by sequential reduction and acylation. The obtained azidopyridines are converted into the corresponding 1,2,3-triazoles when treated with 1,3-dicarbonyl compounds in the presence of Et3N. Field studies showed that some of the synthesized compounds were effective growth regulators of wheat