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Paper | Regular issue | Vol 43, No. 1, 1996, pp.63-70
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7216
Eschenmoser Reaction: An Unexpected Route to Tetrahydrothieno[2,3-b]pyridin-3-ones and Azepan-3-ones

Patrice Marchand, Christian Bellec, Marie-Claude Fargeau-Bellassoued, Cécile Nezry, and Gérard Lhommet*

*Université Pierre et Marie Curie, Laboratoire de Chimie des Hétérocycles, associe au CNRS, 4, Place Jussieu, 75252 Paris Cedex 05, France


Eschenmoser condensation of various commercial secondary α-bromo esters (2) with six and seven membered thiolactams (1) surprisingly gives tetrahydrothieno[2,3-b]pyidin-3-ones and azepan-3-ones and azepan-3-ones (4), while ethyl bromoacetate yields, after sulfur extrusion, the expected cyclic β-enamino esters (3).