Premium
The substitution reaction of pyrazine‐2,3‐dicarbonitrile derivatives with ammonia, amines, water and alcohols
Author(s) -
Hirano Hideki,
Lee Rachel,
Tada Masaru
Publication year - 1982
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.5570190631
Subject(s) - chemistry , pyrazine , ammonia , medicinal chemistry , substitution reaction , base (topology) , derivative (finance) , organic chemistry , substitution (logic) , ring (chemistry) , reaction conditions , aryl , catalysis , alkyl , mathematical analysis , mathematics , computer science , financial economics , economics , programming language
5‐Arylpyrazine‐2,3‐dicarbonitriles 1 and 2 give 2‐alkylamino‐5‐arylpyrazine‐3‐carbonitriles 3 and 5 and 3‐alkylamiono‐5‐arylpyrazine‐2‐carbonitriles 4 and 6 by the substitution reaction with amines but give only 3‐aminopyrazine‐2‐carbonitrile derivative on the reaction with ammonia. The reaction of 5‐arylpyrazine‐2,3‐dicarbonitriles ( 1 and 2 ) with alcohols in the presence of a base gives 2‐alkoxypyrazine‐3‐carbonitrile derivatives 9 and 13 and 3‐alkoxypyrazine‐2‐carbonitrile derivatives 10 and 14 . The reaction of water gives two pyrazinonecarbonitrile derivatives 11 and 12 . In these reactions the aryl groups on the pyrazine ring are 3,4‐dimethoxyphenyl and benzo‐15‐crown‐5.