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Studies on ketene and its derivatives. Part 119 . Reactions of haloketenes with 2‐arylideneaminopyridines
Author(s) -
Katagiri Nobuya,
Kato Tetsuzo,
Niwa Ryuji
Publication year - 1984
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.5570210227
Subject(s) - chemistry , ketene , propanoic acid , ring (chemistry) , medicinal chemistry , stereochemistry , organic chemistry
Reactions of haloketenes with 2‐arylideneaminopyridines were examined. Reaction of dichloroketene with 2‐benzylideneaminopyridines gave 2,2‐dichloro‐3‐phenyl‐3‐(2‐pyridylamino)propanoic acids and 3‐chloro‐2‐phenylpyrido[1,2‐ a ]pyrimidin‐4(4 H )‐ones. Similar reaction of dichloroketene with 2‐(2‐furfurylideneamino)‐pyridines gave 3‐chloro‐2‐(2‐furyl)pyrido[1,2‐ a ]pyrimidin‐4‐(4 H )‐ones. Chloroketene and chlorophenylketene also reacted with 2‐arylideneaminopyridines to give pyrido[1,2‐ a ]pyrimidin‐4(4 H )‐ones. Ring transformations of pyrido[1,2‐ a ]pyrimidin‐4‐(4 H )‐ones were carried out to give 1,8‐naphthyridin‐4(1 H )‐ones and imidazo[1,2‐ a ]‐pyridines.