Novel bicycloannulation via tandem vinylation and intramolecular Diels-Alder reaction of five-membered heterocycles: a new approach to construction of psoralen and …

…, M Yodo, S Ohsuki, K Kanematsu

Index: Hayakawa, Kenji; Yodo, Mitsuaki; Ohsuki, Satoru; Kanematsu, Ken Journal of the American Chemical Society, 1984 , vol. 106, # 22 p. 6735 - 6740

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Citation Number: 95

Abstract

Abstract: trans-4-(Phenylsulfinyl)-3-buten-2-one (1) was found to undergo a new versatile addition-elimination reaction with five-membered compounds such as furans, pyrroles, imidazole, pyrazole, and 6-(dimethylamino) fulvene to give an excellent yield of the corresponding trans-4-aryl-3-buten-2-ones (3). The thermal reaction of the propargyl ethers 7a, b prepared from 3a, b gave a single intramolecular Diels-Alder adduct, 8a, b, in 59% ...