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- Title
New Synthetic Approach to Naphtho[1,2 -b]furan and 4′-Oxo-Substituted Spiro[cyclopropane-1,1′(4′ H)-naphthalene] Derivatives.
- Authors
Arrault, Axelle; Mérour, Jean-Yves; Léger, Jean-Michel; Jarry, Christian; Guillaumet, Gérald
- Abstract
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).
- Publication
Helvetica Chimica Acta, 2001, Vol 84, Issue 8, p2198
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/1522-2675(20010815)84:8<2198::AID-HLCA2198>3.0.CO;2-J