Tetrahedron letters

A one-pot synthesis of thiophene and pyrrole derivatives from readily accessible 3, 5-dihydro-1, 2-dioxines

CE Hewton, MC Kimber, DK Taylor

Index: Hewton, Cassie E; Kimber, Marc C; Taylor, Dennis K Tetrahedron Letters, 2002 , vol. 43, # 17 p. 3199 - 3201

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Citation Number: 36

Abstract

A one-pot synthesis of 2, 5-disubstituted thiophene, 1, 2, 5-tri-and 2, 5-disubstituted pyrrole derivatives from readily available 3, 5-dihydro-1, 2-dioxines is described. The reaction proceeds by an initial Kornblum–de la Mare rearrangement of the 3, 5-dihydro-1, 2-dioxine to its isomeric 1, 4-diketone followed by condensation of the in situ 1, 4-diketone with sulfur, ammonia or a primary amine.