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Derivation of fluorine‐containing pyridine dicarboxylates IV . N ‐substituted dihydropyridine derivatives
Author(s) -
Chupp John P.
Publication year - 1990
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.5570270634
Subject(s) - chemistry , acylation , deprotonation , pyridine , alkylation , sequence (biology) , fluorine , organic chemistry , medicinal chemistry , stereochemistry , combinatorial chemistry , ion , catalysis , biochemistry
The bio‐activity observed for certain Hantzsch derived fluorine‐containing dihydropyridinecarboxylates 6, 11 and 12 and pyridinecarboxylates 10 prompted the preparation of a number of related N ‐substituted dihydropyridines for the first time. One method involved a mixed Hantzsch sequence to give 2 from which unexpected side products 3–5 were also isolated and identified. A second preparative method relied on lithiobase deprotonation of 6, 11 and 12 followed by alkylation or acylation to give products 7–9 and 13–15 . Structure determination and stereo‐assignments are discussed in terms of their spectral properties, and reaction mode.