Journal of the American Chemical Society

Reactions of Naphthoquinones with Malonic Ester and its Analogs. IV. A Synthesis of 2, 3-Disubstituted-4, 5-phthaloylfurans

EF Pratt, RG Rice

Index: Pratt; Rice Journal of the American Chemical Society, 1957 , vol. 79, p. 5489

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Citation Number: 16

Abstract

A 78% yield of 2-phenyl-3-cyano-4, 5-phthaloylfuran(X) is obtained readily upon warming benzoylacetonitrile and 2, 3-dichloro-1, 4-naphthoquinone (I) with pyridine in ethanol. With tributylarnine in place of the pyridine analogous phthaloylfurans (XI and XII) are obtained from acetyl-or benzoylacetone and the dichloroquinone in about 15% yield. The same three (X, XI and XI) and two additional furans (XIII and XIV) are obtained, in 35% average yield, ...