A new coumarin synthesis and its utilization for the synthesis of polycyclic coumarin compounds with anticarcinogenic properties

RG Harvey, C Cortez, TP Ananthanarayan…

Index: Harvey; Cortez; Ananthanarayan; Schmolka Journal of Organic Chemistry, 1988 ,  vol. 53,  # 17  p. 3936 - 3943

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Citation Number: 84

Abstract

A novel synthesis of coumarins based on the ortho-directed metalation of methoxymethyl phenolic ethers with alkyllithium reagents is described. The method entails reaction of the ortho-lithiated intermediates with dimethylformamide to yield the corresponding ortho- aldehydes. Reaction of the latter with lithio-N, N-dimethylacetamide affords the addition products which on heating in refluxing acetic acid undergo smooth conversion directly to ...