Furan derivatives. II. The cyclization of 3-(benzofuran-3-yl)propionic acid derivatives.
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概要
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A compound, 6-methoxy-2a,3,4,5-tetrahydro-2<I>H</I>-naphtho[1,8-<I>bc</I>]furan-5-one (XX), was prepared in a 72% yield by heating 3-(5-methoxy-2,3-dihydrobenzofuran-3-yl)propionic acid (XIX) with polyphosphoric acid. However, when 3-(5-methoxybenzofuran-3-yl)propionic acid (IX) or 3-(2-benzoyl-5-methoxybenzofuran-3-yl)propionic acid (XIII) were treated with polyphosphoric acid, the product was 7-methoxy-2,3-dihydro-1<I>H</I>-cyclopenta[<I>b</I>]benzofuran-3-one (XI) rather than the corresponding naphtho[1,8-<I>bc</I>]furan derivatives, Also, neither naphtho[1,8-<I>bc</I>]furan nor cyclopenta[<I>b</I>]benzofuran derivatives were obtained from 3-(2-benzyl-5-methoxybenzofuran-3-yl)propionic acid (XIV) or 3-(2-ethyl-5-methoxybenzofuran-3-yl)propionic acid (XVII).
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