One-step preparation of 3-alkoxypyrazine-2-carbonitriles from pyrazine-2,3-dicarbonitriles and related reactions

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.