Chemistry of thienopyridines. XXXII. Direct introduction of C??substituents gamma to the heteronitrogen atom in the thieno [2, 3??b] pyridine system

LH Klemm, DR Muchiri, JN Louris

文献索引：Klemm, L. H.; Muchiri, Daniel R.; Louris, John N. Journal of Heterocyclic Chemistry, 1984 , vol. 21, p. 1135 - 1140

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被引用次数: 9

摘要

Abstract Treatment of the N-oxide 1a of thieno [2, 3-b] pyridine (1) with either (a) acetic anhydride and ethyl cyanoacetate or (b) benzoyl chloride and an enamine of cyclohexanone (Hamana reactions) serves to introduce a C-substituent at the 4-position of 1. In case (a) one obtains a yellow, isolable vinylogous N-ylide 5 (23% yield), which undergoes facile transformation into ethyl 2-(4-thieno [2, 3-b] pyridyl) cyanoacetate (1e)(88–93%). Acetic ...