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Reaction of the pyrazinium ion having aryl and cyano groups with hydride reagents or hydroxide ion
Author(s) -
Hirano Hadeki,
Tada Masaru
Publication year - 1981
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.5570180511
Subject(s) - chemistry , reagent , sodium borohydride , hydroxide , hydride , derivative (finance) , sodium hydroxide , ion , inorganic chemistry , sodium hydride , aryl , sodium , medicinal chemistry , organic chemistry , metal , catalysis , alkyl , financial economics , economics
Reduction of 3‐cyano‐5‐(3,4‐dimethoxyphenyl)‐1‐methylpyrazinium ion by the hydride reagents such as sodium borohydride or Hantzsch ester gave the 1,6‐dihydropyrazine derivative, and the 1,4,5,6‐tetra‐hydropyrazine derivative on further reduction. Addition of hydroxide ion to the pyrazinium ion gave mainly a 6‐hydroxy‐pseudobase, accompanied by the minor formation of a 2‐hydroxy‐pseudobase. Photoreaction of the pseudobase mixture gave a product from the major pseudobase but thermal transformation gave another product from the minor pseudobase.