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Synthesis and structural characterization of substituted thieno[2,3‐ b ]pyridines from o ‐chloroformyl‐1,4‐dihydropyridines
Author(s) -
Suárez Margarita,
Ochoa Estael,
Pita Beatriz,
Espinosa Remberto,
González Leandro,
Martín Nazario,
Quinteiro Margarita,
Seoane Carlos,
Soto Jose L.
Publication year - 1997
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570340334
Subject(s) - chemistry , ring (chemistry) , characterization (materials science) , dihydropyridine , planar , computational chemistry , charge (physics) , stereochemistry , crystallography , organic chemistry , nanotechnology , computer graphics (images) , physics , materials science , quantum mechanics , computer science , calcium
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.