Transformations of 1, 2, 4-Triazines in Reactions with Nucleophiles: V. SNH and ipso-Substitution in the Synthesis and Transformations of 5-Cyano-1, 2, 4-triazines

DN Kozhevnikov, VN Kozhevnikov, IS Kovalev…

Index: Kozhevnikov; Kovalev; Rusinov; Chupakhin; Aleksandrov Russian Journal of Organic Chemistry, 2002 , vol. 38, # 5 p. 744 - 750

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Citation Number: 7

Abstract

Abstract The scope of functionalization of 1, 2, 4-triazines can be considerably extended via successive nucleophilic substitution of hydrogen (SNH) and ipso-substitution. A convenient procedure has been developed for direct cyanation of 1, 2, 4-triazine 4-oxides with acetone cyanohydrin in the presence of triethylamine. The cyano group in the resulting 5-cyano-1, 2, 4-triazines is readily replaced by reactions with various aliphatic alcohols and amines.