ChemInform Abstract: Vinylindenes and Some Heteroanalogues in the Diels-Alder Reaction. Part 9. 3-Vinylbenzofuran and 1,4-Naphthoquinone.
Abstract
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ChemInform Abstract
Several methods are discussed for the preparation of 3-vinylbenzofuran (VIII); the key step of the most convenient synthesis involves the condensation of the enamine (III) with cyanoacetic acid (IV) and subsequent decarboxylation to give the cyanide (V). Reaction of (VIII) with the naphthoquinone (IX) leads to the adduct (X), which undergoes ring opening to the anthraquinone (XI), but shows no rearrangement to a “linear” quinone as is observed for the thio analogue (XII) (not all yields given).
