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Reissert compound studies. LXVII . The pyrido[3,4‐ b ]pyrazine reissert compound
Author(s) -
Duarte Frederick F.,
Popp Frank D.
Publication year - 1994
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.5570310422
Subject(s) - chemistry , pyrazine , alkylation , trimethylsilyl cyanide , trimethylsilyl , medicinal chemistry , benzene , halide , chloroformate , organic chemistry , catalysis
The pyrido[3,4‐ b ]pyrazine systems investigated were found to form Reissert compounds in the presence of an acyl halide (or chloroformate) and trimethylsilyl cyanide. Only the mono Reissert compounds were isolated. In the case of 2,3‐diphenylpyrido[3,4‐ b ]pyrazine ( 7 ), its reaction with benzene sulfonyl chloride and trimethylsilyl cyanide gave 5‐cyano‐2,3‐diphenylpyrido[3,4‐ b ]pyrazine ( 16 ). Alkylation of the Reissert compound 11 and analog 12 either directly gave the alkylated hetercyclic base or the alkylated Reissert analog compound.