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Synthesis of 3,5‐disubstituted 1‐amino‐1,3,5‐triazine‐2,4,6‐triones (or 1‐aminocyanurates) by cyclic transformation of 1,3,4‐oxadiazol‐2(3 H )‐one derivatives
Author(s) -
Chau François,
Malanda JeanClaude,
Milcent René
Publication year - 1997
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.5570340536
Subject(s) - chemistry , sodium hydride , aryl , hydrolysis , 1,3,5 triazine , dimethylformamide , anhydrous , triazine , medicinal chemistry , derivative (finance) , sodium azide , organic chemistry , alkyl , financial economics , economics , solvent
The 5‐aryl(or methyl)‐3‐phenylcarbamoyl‐1,3,4‐oxadiazol‐2(3 H )‐ones 2 , in the presence of sodium hydride in anhydrous dimethylformamide, were transformed into 1‐benzamido(or acetamido)‐3,5‐diphenyl‐1,3,5‐triazine‐2,4,6‐trione derivatives 7 in poor yields. However, compounds 7 were obtained in better yields when the sodium salts of 5‐aryl(or methyl)‐1,3,4‐oxadiazol‐2(3 H )‐ones 1 were treated with two equivalents of aryl(or ethyl)isocyanates. Acidic hydrolysis of 1‐acetamido‐3,5‐diphenyl‐1,3,5‐triazine‐2,4,6‐trione ( 7i ) provided the corresponding free N ‐amino derivative 9 . Nitrous deamination of 9 gave the known 3,5‐diphenyl‐1,3,5‐triazine‐2,4,6‐trione ( 11 ). This cyclic transformation is the first one to be reported providing 1,3,5‐triazine‐2,4,6‐trione derivatives.