Tetrahedron

A practical synthesis of flavones from methyl salicylate

D Nagarathnam, M Cushman

Index: Nagarathnam, Dhanapalan; Cushman, Mark Tetrahedron, 1991 , vol. 47, # 28 p. 5071 - 5076

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Citation Number: 33

Abstract

A facile synthetic method has been developed for the conversion of methyl salicylate (5) into flavones 1a-i in high yields. Compound 5 on treatment with t-butyldimethylsilyl chloride (6) gave the O-silyl protected ester 7. Condensation of this ester 7 with the lithium anion generated from acetophenones 3a-i yielded the 1.3-diarylpropane-1, 3-diones 8a-i, which on treatment with glacial acetic acid containing 0.5% H2SO4 for 3 h at 95-100° C provided ...

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