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A short and general synthesis of 1,3‐dihydro‐6‐heteroaryl‐5‐perfluoroalkyl‐2 H ‐imidazo[4,5‐ b ]pyridin‐2‐ones
Author(s) -
Kuo GeeHong,
Bacon Edward R.,
Singh Baldev,
Eissenstat Michael A.,
Lesher George Y.
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.5570300107
Subject(s) - chemistry , hydrolysis , medicinal chemistry , stereochemistry , azide , organic chemistry
Trifluoro or pentafluoroacylation of heteroaryl‐enamines 2a,b gave the corresponding perfluoroacylated heteroaryl‐enamines 3a‐c . Heating the latter compounds with diethyl iminomalonate gave 2‐amino‐3‐pyridinecarboxylates 4a‐c . Hydrolysis to the free acids 5a‐c , and reaction with diphenylphosphoryl azide afforded the desired 1,3‐dihydro‐6‐heteroaryl‐5‐perfluoroalkyl‐2 H ‐imidazo[4,5‐ b ]pyridin‐2‐ones 6a‐c .