Synthesis of 3-Alkoxymethylcoumarin from 3-Cyanochromene via a Novel Intermediate 2-Phenylimino-3-alkoxymethylchromene

…, MY Chiang, LY Chen, PY Chen, YF Lo…

Index: Tsai, Jui-Chi; Li, Sie-Rong; Chiang, Michael Y.; Chen, Lian-Yeu; Chen, Po-Yuan; Lo, Yi-Fang; Wang, Chen-Hao; Lin, Chun-Nan; Wang, Eng-Chi Journal of Organic Chemistry, 2009 , vol. 74, # 22 p. 8798 - 8801

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Citation Number: 2

Abstract

In this paper a concise, efficient, and environmentally benign method for the synthesis of 3- alkoxymethylcoumarin is described. From the reaction of 3-cyanochromene with an alkoxide and arylamine in THF,(Z)-2-phenylimino-3-alkoxymethylchromene was obtained as a novel intermediate via an isomerization of the double bond, a 1, 2-addition of alkoxide, a Michael- type addition of aniline, an another isomerization of double bond and an elimination of ...