Tetrahedron

Synthesis of benzo [d]-1, 2-thiazole-1, 1-dioxide derivatives via directed lithiation of 2, 2-dimethyl-N-(phenylsulfonyl)-propanamides

P Stanetty, B Krumpak, T Emerschitz, K Mereiter

Index: Stanetty, Peter; Krumpak, Barbara; Emerschitz, Thomas; Mereiter, Kurt Tetrahedron, 1997 , vol. 53, # 10 p. 3615 - 3626

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Citation Number: 8

Abstract

A novel synthesis of 7-substituted benzo [d]-1, 2-thiazole-1, 1-dioxides 4 is presented including directed lithiation of 2, 2-dimethyl-N-(phenylsulfonyl)-propanamides 1–3, aryne- mediated cyclization and subsequent quenching of aryllithium intermediates with various electrophiles. A proposed mechanism is rationalized by some control experiments.