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Derivation of fluorine‐containing pyridine dicarboxylates. II . Elaboration at the 4‐position
Author(s) -
Chupp John P.,
Molyneaux John M.
Publication year - 1989
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.5570260325
Subject(s) - chemistry , pyridine , aldehyde , ring (chemistry) , enamine , alkyl , fluorine , derivative (finance) , sulfur , medicinal chemistry , stereochemistry , carbonyl group , organic chemistry , catalysis , financial economics , economics
In response to the bio‐activity found in fluorine‐containing 4‐alkyl‐3, 5‐pyridinedicarboxylates, a series of novel 4‐substituted derivatives, not directly available by Hantzsch sequences, were prepared. Starting 4‐alkylpyridines, 1 , were converted via enamine 2 to materials 3–8 . Derivatives 9–16 in turn were derived from aldehyde 3 , while acid derivatives 28–36 were prepared from 14 . Addition of oxygen, sulfur, and carbenoids effected conversion of 4‐allylpyridine 16 to epoxy and cyclopropyl derivative 16–22 . A number of neighboring group effects were noted, including those forming the fused‐ring systems 23‐27 .