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Synthesis and structural characterization of substituted thieno[2,3-b]pyridines from o-chloroformyl-1,4-dihydropyridines
✍ Scribed by Margarita Suárez; Estael Ochoa; Beatriz Pita; Remberto Espinosa; Leandro González; Nazario Martín; Margarita Quinteiro; Carlos Seoane; Jose L. Soto
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1997
- Tongue
- English
- Weight
- 331 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
Novel 4,7‐dihydrothieno[2,3‐b]pyridines 10a‐d have been prepared in a one step procedure from the readily available o‐chloroformyl substituted 1,4‐dihydropyridines 9a‐d and ethyl mercaptoacetate in good yields. Semiempirical calculations reveal a favoured geometry with a boat conformation in the dihydropyridine system and a planar thieno ring. The calculated charge density values for the olefmic carbons (C5 and C6) are in agreement with the experimental push‐pull effect observed in the ^13^C nmr.
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