REACTIONS OF 2-ARYLHYDRAZONOACETAMIDES WITH ORTHOESTERS. SYNTHESIS OF NEW TETRAHYDRO-1,2,4-TRIAZINES

Abstract

The reactions of arylhydrazonocyanoacetamides with triethyl orthoformate and triethyl orthoacetate have been studied. Interaction of triethyl orthoformate with amides bearing normal alkyl substituents on the carbamoyl group resulted in cyclization to 2-aryl-4-alkyl-5-oxo-3-ethoxy-2,3,4,5-tetrahydro-1,2,4-triazin-6-carbonitriles, whereas reaction of N-phenyl- and N-cycloalkylacetamides with triethyl orthoformate gave products of ethylation at the hydrazone group. Reactions of arylhydrazonocyanoacetamides with triethyl orthoacetate led to 2-(arylethylhydrazono)acetamides exclusively.

Authors: N. P. Bel'skaya, E. E. Zvereva, L. A. Babushkina, and V. A. Bakulev.

English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (9), pp 1066-1076

http://link.springer.com/article/10.1023/A%3A1002738100046