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The synthesis and chemistry of 2‐hydroxy‐4,6‐bis(trifluoromethyl)pyridine‐5‐carboxylates
Author(s) -
Goure William F.
Publication year - 1993
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.5570300114
Subject(s) - chemistry , trifluoromethyl , pyridine , electrophile , condensation , chloride , intramolecular force , medicinal chemistry , organic chemistry , catalysis , alkyl , physics , thermodynamics
The facile two step, one pot synthesis of heretofore unknown 2‐hydroxy‐4,6‐bis(trifluoromethyl)‐pyridine‐5‐carboxylates by condensation of 3‐amino‐4,4,4‐trifluoro‐2‐butenoate with 4,4,4‐trifluoroacetoacetyl chloride and subsequent intramolecular cyclization of the resultant enamineamide is described. Methodology for the introduction of electrophiles at the 3‐position and elaboration of substituents at the 2‐ and 5‐positions is also discussed.