Dehydration of 2-Hydroxyimines with Dicyclohexylcarbodiimide: An Access to Cyclic Alkenylimines

Abstract
2-Methyl-1-aza-1-cycloalkenes 1 react with aldehydes and ketones to yield 2-(2-hydroxyalkyl)-1-aza-1-cycloalkenes 3 under basic conditions. The resulting 2-hydroxyimines 3 are easily dehydrated by dicyclohexylcarbodiimide (DCC) with copper(I) chloride as catalyst in refluxing ether to furnish the corresponding 2-(1-alkenyl)-1-aza-1-cycloalkenes 4.

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