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Reaction of pyrazine‐2,3‐dicarbonitrile and 1,3‐dimethyllumazine with the phthalimidoalkyl radical
Author(s) -
Tada Masaru,
Totoki Shintaro
Publication year - 1988
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.5570250505
Subject(s) - chemistry , pyrazine , pteridine , hydrazine (antidepressant) , free radical reaction , medicinal chemistry , derivative (finance) , organic chemistry , radical , chromatography , financial economics , economics , enzyme
A phthalimidoalkyl radical reacts with pyrazine‐2,3‐dicarbonitrile ( 1 ) to give mono‐ and diphthalimido‐alkylpyrazine‐2,3‐dicarbonitriles 4 and 5 . A similar reaction with 1,3‐dimethyllumazine ( 2 ) gave only monophthalimidoalkyl‐1,3‐dimethyllumazines 6 or 7 . Hydrazine degradation of 7‐(3′‐phthalimido)propyl‐1,3‐dimethyllumazine ( 6c ) gave a 7‐(3′‐amino)propyl derivative 8 but 7‐phthalimidomethyl‐1,3‐dimethyllumazine ( 6a ) gave only 1,3‐dimethyllumazine ( 2 ). Thus the phthalimidomethyl group can be used as a protection group of the pteridine nucleus.