Journal of heterocyclic chemistry

Preparation of alkyl substituted 1, 3, 4??oxadiazin??6??ones by the DCC induced cyclization of 2??oxoalkanoic acid acylhydrazones

A Padwa, P Eisenbarth

Index: Padwa, Albert; Eisenbarth, Philipp Journal of Heterocyclic Chemistry, 1985 , vol. 22, p. 61 - 64

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Citation Number: 6

Abstract

Abstract A series of 2, 5-disubstituted 1, 3, 4-oxadiazin-6-ones were prepared by treating syn- 2-oxoalkanoic acid acylhydrazones with dicyclohexylcarbodiimide. The isomeric anti isomers produced acylureas when treated with DCC. The cycloaddition reaction of 5-methyl- 2-phenyl-1, 3, 4-oxadiazin-6-one with norbornene was studied and found to give a nitrogen deficient 1: 1-cycloadduct. The formation of the product can be rationalized in terms of a ...