Premium
Reaction of 5‐(3,4‐dimethoxyphenyl)pyrazine‐2,3‐dicarbonitrile with alcohol in the presence of base
Author(s) -
Tsuzuki Koichi,
Tada Masaru
Publication year - 1985
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.5570220546
Subject(s) - chemistry , pyrazine , methanol , solvent polarity , substitution (logic) , selectivity , base (topology) , medicinal chemistry , alcohol , solvent , substitution reaction , organic chemistry , catalysis , mathematical analysis , mathematics , computer science , programming language
5‐(3,4‐Dimethoxyphenyl)pyrazine‐2,3‐dicarbonitrile reacts with methanol to give addition products, 3‐methoxyiminopyrazine‐2‐carbonitrile and 2‐methoxyiminopyrazine‐3‐carbonitrile derivatives, and/or substitution products, 3‐methoxypyrazine‐2‐carbonitrile and 2‐methoxypyrazine‐3‐carbonitrile derivatives. The selectivity between the addition and substitution depends on solvent polarity, base, and reaction time. The experimental results are accounted for by the equilibrium between the starting dinitrile and the addition products, methoxyiminopyrazine.