FURAN RING-OPENING REACTIONS OF 5-HYDROXY-2, 3-DIHYDROBENZO [B] FURANS

Abstract:

A furan ring opening of benzo [b] furans (1a-c) under acetylation and methylation conditions was carried out. The reaction of these heterocycles with acetic anhydride-pyridine mixture afforded the corresponding 1, 4-disubstituted buta-1, 3-dienes (3a-c). Compound (3c) reacts with dimethyl sulfate under basic conditions to give 1-methoxy-4-(3, 6-dimethoxy-2-nitrophenyl)-buta-1, 3-diene (5) in 95% yield. Some evidences on the participation of carbanion intermediates and a possible reaction course for the furan ring opening of heterocycles (1a-c) are presented.

Año de publicación:

1993

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