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Reaction of N,N ‐dimethylazidochloromethyleniminium chloride (azidophosgeniminium chloride) with 1,3‐dimethyl‐4‐aminouracils. A new “one pot” synthesis of 3‐aryl‐(and 3‐alkyl)‐4,6‐dimethyl‐5,7‐dioxo‐1,2,3‐triazolo[4,5‐ d ]pyrimidines (8‐azatheophyllines) via a diazo group transfer process
Author(s) -
Kokel Bruno,
Boussouira Nadia
Publication year - 1987
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.5570240601
Subject(s) - chemistry , alkyl , diazo , aryl , yield (engineering) , chloride , medicinal chemistry , organic chemistry , materials science , metallurgy
N,N ‐Dimethylazidochloromethyleniminium chloride (azidophosgeniminium chloride) ( 1 ) reacts by diazo group transfer with 1,3‐dimethyl‐4‐aryl‐(and alkyl)aminouracils 4 to give, under mild “one pot” reaction conditions, a very good yield of 3‐aryl‐(and 3‐alkyl)‐4,6‐dimethyl‐5,7‐dioxo‐1,2,3‐triazolo[4,5‐ d ]pyrimidines (8‐azatheophyllines) 8 . That reaction proceeds, very likely, through formation of non‐isolated 4‐imino‐5‐diazouracils 6 .