Premium
Synthesis of methylpyridine derivatives. XXXV . Reaction of acetylpyridine with phosphoryl chloride to give alkynylpyridine
Author(s) -
Kato Tetsuzo,
Sato Masayuki,
Wagai Akihiro
Publication year - 1981
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.5570180333
Subject(s) - chemistry , phosphoryl chloride , pyrimidine , chloride , medicinal chemistry , 2 pyridone , stereochemistry , organic chemistry
Reaction of 3‐acetyl‐4,6‐dimethyl‐2‐(1 H )pyridone ( 9a ) with phosphoryl chloride gives 2‐chloro‐3‐ethynyl‐4,6‐dimethylpyridine ( 10a ). 3‐Acetyl‐4‐hydroxy‐6‐methyl‐2(1 H )pyridone (14a) and 3‐acetyl‐2,6‐dimethyl‐4‐(1 H )‐pyridone (21) undergoes similar reaction to give the corresponding ethynyl (16 and 23) and chlorovinyl (15 and 22) pyridines, respectively. The chlorination of 3‐acetylpyridine and pyrimidine derivatives is further described.