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New Synthetic Approach to Naphtho[1,2 ‐b ]furan and 4′‐Oxo‐Substituted Spiro[cyclopropane‐1,1′(4′ H )‐naphthalene] Derivatives
Author(s) -
Arrault Axelle,
Mérour JeanYves,
Léger JeanMichel,
Jarry Christian,
Guillaumet Gérald
Publication year - 2001
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20010815)84:8<2198::aid-hlca2198>3.0.co;2-j
Subject(s) - chemistry , cyclopropane , furan , naphthalene , ring (chemistry) , reactivity (psychology) , stereochemistry , medicinal chemistry , carboxylate , organic chemistry , medicine , alternative medicine , pathology
A one‐step synthesis of ethyl 2,3‐dihydronaphtho[1,2‐ b ]furan‐2‐carboxylate and/or ethyl 4′‐oxospiro[cyclopropane‐1,1′(4′ H )‐naphthalene]‐2′‐carboxylate derivatives 2 and 3 , respectively, from substituted naphthalen‐1‐ols and ethyl 2,3‐dibromopropanoate is described ( Scheme 1 ). Compounds 2 were easily aromatized ( Scheme 2 ). In the same way, 3,4‐dibromobutan‐2‐one afforded the corresponding 1‐(2,3‐dihydronaphtho[1,2‐ b ]furan‐2‐yl)ethanone and/or spiro derivatives 8 and 9 , respectively ( Scheme 6 ). A mechanism for the formation of the dihydronaphtho[1,2‐ b ]furan ring and of the spiro compounds 3 is proposed ( Schemes 3 and 4 ). The structures of spiro compounds 3a and 3f were established by X‐ray structural analysis. The reactivity of compound 3a was also briefly examined ( Scheme 9 ).