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Regioselective conversion of 3‐cyano‐6‐hydroxy‐2‐pyridones into 3‐cyano‐6‐amino‐2‐pyridones
Author(s) -
Katritzky Alan R.,
Rachwal Stanislaw,
Smith Terrance P.
Publication year - 1995
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.5570320356
Subject(s) - chemistry , tautomer , regioselectivity , ammonia , pyridine , liquid ammonia , medicinal chemistry , organic chemistry , catalysis
The reaction of a tautomeric mixture of 1‐butyl‐1,2‐dihydro‐6‐hydroxy‐4‐methyl‐2‐oxopyridine‐3‐carbonitrile and its 2‐hydroxy‐6‐oxo analog with phosphorus oxychloride gave 1‐butyl‐6‐chloro‐1,2‐dihydro‐4‐methyl‐2‐oxopyridine‐3‐carbonitrile (68%) and 1‐butyl‐2‐chloro‐1,6‐dihydro‐4‐methyl‐6‐pyridine‐3‐car‐bonitrile (3%). Both chloropyridones were converted to their corresponding aminopyridones by reaction with liquid ammonia. Strong support for the molecular structure of 6‐amino‐1‐butyl‐1,2‐dihydro‐4‐methyl‐2‐oxopyridine‐3‐carbonitrile was obtained on the basis of nmr techniques.