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

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...

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Bibliographic Details
Published inHeterocycles Vol. 36; no. 12; pp. 2819 - 2828
Main Authors VALDERRAMA, JA, GONZALEZ, MF, ARIAS, P, PESSOAMAHANA, H, TAPIA, R
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.12.1993
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACTIVATED QUINONES
REARRANGEMENT
ENAMINES
DIELS-ALDER ADDUCTS
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Summary: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.
ISSN:0385-5414
DOI:10.3987/com-93-6529