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New syntheses and spectral properties of pteridine‐related heterocycles from 2,5‐diamino‐3,6‐dicyanopyrazine
Author(s) -
Shirai Kazuko,
Fukunishi Koushi,
Yanagisawa Atsushi,
Takahashi Hiroshi,
Matsuoka Masaru
Publication year - 2000
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.5570370521
Subject(s) - chemistry , pteridine , isocyanate , alkyl , pyrazine , sodium hydride , adduct , iodide , organic chemistry , medicinal chemistry , amine gas treating , morpholine , ethyl iodide , polyurethane , enzyme
The reaction of 2,5‐diamino‐3,6‐dicyanopyrazine ( 1 ) as a new pyrazine raw material with alkyl isocyanate in the presence of sodium hydride gave novel heptahydroirnidazo[4,5‐ g ]pteridine‐2,6,8‐trione ( 2 ), but with tertiary butyl isocyanate gave trihydroimidazo[4,5‐ b ]pyrazine‐2‐ones ( 3 ). Similar reaction of 1 with alkyl thioisocyanate followed by alkyl iodide gave tetrahydropyrimido[4,5‐ g ]pteridines ( 4 ). The reac tion of 1 with alkylamine gave the amine‐adduct of the cyano groups which was further reacted with arylaldehyde to give the pyrimido[4,5‐ g ]pteridine ( 10 ). The products prepared are all of interest as potential pesticides and fluorescent chromophores.