The Reaction of β-Amino α,β-Unsaturated Esters with Amines

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概要

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• The reactions between amines and 1,4-bis(ethoxycarbonyl)-2,5-bis(alkyl- or arylamino)-1-4-cyclohexadiene(I) and its analogs are studied. The main products are <I>N</I>,<I>N</I>′-disubstituted urea(II) and 1,4-bis(alkyl- or arylamino)-1,4-cyclohexadiene(V) instead of the expected carboxamide. The presence of small amounts of ethyl <I>N</I>-substituted carbamate (III) in the products leads to the conclusion that the reaction proceeds through two successive steps: the nucleophilic attack by an amine upon a carbonyl carbon atom of the ethoxycarbonyl group, with a cleavage of a carbon-carbon bond to give III and V, and the amidation of III <I>in situ</I>, giving II. The rate of the second step is much faster than that of the first step. The formation of II occurs in the compounds with a β-amino α,β-unsaturated carbonyl group.

• 公益社団法人 日本化学会の論文

著者

• Tai Akira

  Research Center of Tekkosha Co., Ltd.

• Yokoyama Yasukazu

  Research Center of Tekkosha Co., Ltd.

関連論文

• The Reaction of β-Amino α,β-Unsaturated Esters with Amines
• The Reactions of β-Amino α,β-Unsaturated Esters with Amines. II. Syntheses of Some New Derivatives of Quinazolines

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