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Preparation of New Nitrogen-Bridged Heterocycles. 35. Smooth Synthesis of 10a H -Pyrido[1,2- d ][1,4]thiazepine Derivatives

1993; Oxford University Press; Volume: 66; Issue: 11 Linguagem: Inglês

10.1246/bcsj.66.3475

1348-0634

Akikazu Kakehi, Suketaka Ito, Jun-ichi Hakui,

Chemical Synthesis and Analysis

Abstract Various 1-pyridinio(thiocarbonyl)methylides and 2-isoquinolinio(thiocarbonyl)methylides react smoothly with dimethyl acetylenedicarboxylate at room temperature or at the reflux temperature in chloroform to give new heterocycles, dimethyl 10aH-pyrido[1,2-d][1,4]thiazepine-1,2-dicarboxylate derivatives, in moderate yields. Similarly, the reactions of some 3-(1-pyridinio)thiophene-2-thiolates with the same reagent afforded the corresponding dimethyl 6aH-pyrido[1,2-d]thieno[2′,3′-b][1,4]thiazepine-5,6-dicarboxylates. The structures of these 1,4-thiazepine derivatives were mainly assigned based on physical and spectral inspections, and were finally confirmed by X-ray analyses of three compounds.