Synthesis and structural characterization of substituted thieno[2,3-b]pyridines from o-chloroformyl-1,4-dihydropyridines
1997
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 13C nmr.
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