Tetrahedron

Dihydrothiophenes as precursors to fused quinolines, quinolones and coumarins via o-quinodimethane intermediates

LA White, RC Storr

Index: White, Lindsay A.; Storr, Richard C. Tetrahedron, 1996 , vol. 52, # 9 p. 3117 - 3134

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Citation Number: 27

Abstract

3-Methoxycarbonyl-4-keto-2, 5-dihydrothiophene is a convenient starting point for synthesis of a range of 3, 4-and 2, 3-quinoline and quinolone and coumarin fused dihydrothiophene dioxides. With the exception of the 2, 3-quinoline derivatives these all lose sulfur dioxide on thermolysis to give the corresponding o-quinodimethanes which can be intercepted in Diels- Alder reactions.