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The syntheses of pteridin‐2‐one derivatives from diaminomaleonitrile (DAMN)
Author(s) -
Tsuzuki Koichi,
Tada Masaru
Publication year - 1986
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.5570230508
Subject(s) - chemistry , pyrazine , glyoxal , pteridine , sodium hydride , nucleophilic substitution , nucleophile , methylamine , medicinal chemistry , stereochemistry , organic chemistry , enzyme , catalysis
1,3‐Dimethyl‐4‐iminopteridin‐2‐one, 1,3‐dimethylpteridine‐2,4‐dione, 1‐methylpteridine‐2,4‐dione, 4‐alkoxy‐1‐methylpteridin‐2‐one, and 4‐alkylamino‐1‐methylpteridin‐2‐one were synthesized from diaminomaleonitrile (DAMN) through pyrazine‐2,3‐dicarbonitrile. The synthetic procedures consist of the condensation of DAMN with glyoxal, the nucleophilic substitution of pyrazine‐2,3‐dicarbonitrile with methylamine, the reaction of 3‐methylaminopyrazine‐2‐carbonitrile with electrophiles such as methyl isocyanate and methyl chloroformate in the presence of sodium hydride, and the transformation of 3‐(methoxycarbonylmethyl)aminopyrazine‐2‐carbonitrile into the pteridine derivatives.