Abstract
A simple, general route to the 1,2-dihydronaphtho[2,1-b]furans and 2,3-dihydrobenzofurans substituted at C-2 by an acyl or aryl group, starting from phenolic Mannich bases and pyridinium ylides, has been developed. The mechanism of the reaction is believed to involve the formation of the o-quinone methide intermediate, Michael-type addition of the ylide to the o-quinone methide, followed by intramolecular nucleophilic substitution.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Benzofurans / chemical synthesis*
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Benzofurans / chemistry
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Furans / chemical synthesis*
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Furans / chemistry
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Molecular Structure
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Naphthalenes / chemical synthesis*
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Naphthalenes / chemistry
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Pyridinium Compounds / chemistry*
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Quinones / chemistry*
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Stereoisomerism
Substances
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1,2-dihydronaphtho(2,1-b)furan
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Benzofurans
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Furans
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Naphthalenes
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Pyridinium Compounds
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Quinones
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coumaran