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

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 dih...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 34; no. 3; pp. 931 - 935
Main Authors Suarez, M, Ochoa, E, Pita, B, Espinosa, R, Gonzalez, L, Martin, N, Quinteiro, M, Seoane, C, Soto, JL
Format Journal Article
LanguageEnglish
Published ODESSA HETERO CORPORATION 01.05.1997
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANTAGONISTS
1,4-DIHYDROPYRIDINES
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Summary: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 olefinic carbons (C5 and C6) are in agreement with the experimental push-pull effect observed in the C-13 nmr.
ISSN:0022-152X
DOI:10.1002/jhet.5570340334