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One‐step preparation of 3‐alkoxypyrazine‐2‐carbonitriles from pyrazine‐2,3‐dicarbonitriles and related reactions
Author(s) -
Kojima Takakazu,
Nagasaki Fumihiko,
Ohtsuka Yozo
Publication year - 1980
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.5570170308
Subject(s) - chemistry , pyrazine , substitution (logic) , substitution reaction , medicinal chemistry , organic chemistry , computer science , programming language
A series of 5,6‐disubstituted 3‐alkoxypyrazine‐2‐carbonitriles ( 2a‐i ) were prepared from 5,6‐disubstituted pyrazine‐2,3‐dicarbonitriles ( 1a‐d ) by direct substitution with alcohols. Treatment of 1 with amines gave either pyrrolopyrazines ( 3a,b ) or substitution products ( 4,5 ). In a low temperature range, 1 afforded imidates and related compounds ( 6–11 ). The preference among these reactions depended on the 5,6‐substituents and on the reaction conditions.