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Reaction of 5‐(3,4‐dimethoxyphenyl)pyrazine‐2,3‐dicarbonitrile with alkyl radicals
Author(s) -
Tada Masaru,
Momose Hiroshi
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.5570220544
Subject(s) - pyrazine , chemistry , alkyl , radical , medicinal chemistry , ring (chemistry) , photochemistry , stereochemistry , organic chemistry
The reaction of 5‐(3,4‐dimethoxyphenyl)pyrazine‐2,3‐dicarbonitrile (Ib) with alkyl radicals gives addition products at the C(6)‐position of the pyrazine ring as the intermediates which collapse into substitution products, 6‐alkyl‐5‐(3,4‐dimethoxyphenylpyrazine‐2,3‐dicarbonitrile (II), under oxidative conditions. Under non‐oxidative conditions the intermediate is converted into dihydropyrazine derivatives, 6‐alkyl‐(3,4‐dimethoxy‐phenyl)‐5,6‐dihydropyrazine‐2,3‐dicarbonitrile (III), and 3,6‐disubstituted pyrazine derivatives, 3,6‐dialkyl‐5‐(3,4‐dimethoxyphenyl)pyrazine‐2‐carbonitrile (IV) and 3‐acyl‐6‐alkyl‐5‐(3,4‐dimethoxyphenyl)pyrazine‐2‐carbonitrile (V).