Synthesis of 4-arylcarbamoyl-5-(2-hydroxynaphthylazo)imidazoles and 1-substituted naphtho[2,1-e]imidazo[5,1-c][1,2,4]triazines

被引：0
|
作者：
E. V. Sadchikova
V. S. Mokrushin
机构：
[1] Ural State Technical University — UPI,
来源：
Russian Chemical Bulletin | 2006年 / 55卷
关键词：
5-diazoimidazoles; 5-imidazolyldiazonium salts; -azo coupling; reactivity; azo compounds; naphtho[2,1-; ]imidazo[5,1-; ][1,2,4]triazines;
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摘要：
The reactions of β-naphthol with 5-diazoimidazoles and imidazolyl-5-diazonium salts containing chemically different carboxamide groups in position 4 were studied. Heterocyclization of 4-arylcarbamoyl-5-(2-hydroxynaphthylazo)imidazoles formed in these reactions was investigated. The presence of the NH fragment in the amide group prevents this process, the reaction giving instead 3-substituted 3,7-dihydroimidazo[4,5-d][1,2,3]triazin-4-ones, which is due to reversibility of C-azo coupling. Methods for modification of 1-ethoxycarbonyl group in the naphtho[2,1-e]imidazo[5,1-c][1,2,4]triazine system were developed and used to prepare substituted carboxamides inaccessible by other routes.
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页码：1255 / 1261
页数：6
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