The synthesis of 5-amino-4-arylazo-3-methyl-1H-pyrazoles and 5-aryl-3-methylpyrazole[3,4-e][1,2,3,4]tetrazines

被引：16
|
作者：
Yang, Bo [1 ]
Lu, Yuan [1 ]
Chen, Chao-Jun [1 ]
Cui, Jian-Ping [1 ]
Cai, Meng-Shen [2 ]
机构：
[1] Inner Mongolia Med Coll, Dept Pharmaceut Sci, Hohhot 010059, Peoples R China
[2] Peking Univ, Sch Pharmaceut Sci, Beijing 10083, Peoples R China
来源：
DYES AND PIGMENTS | 2009年 / 83卷 / 02期
关键词：
5-Amino-4-arylazo-3-methyl-1H-pyrazole; Pyrazolo-tetrazine dyes; AlCl3-catalyst; Diazocoupling reaction; Green chemistry; Intermolecular cyclization; ORGANIC-REACTIONS; WATER; DERIVATIVES;
D O I：
10.1016/j.dyepig.2008.12.011
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
AlCl3-catalyzed coupling of 3-amino-5-methyl-1H-pyrazole in water with different aryldiazonium compounds yielded 5-amino-4-arylazo-3-methyl-1H-pyrazole derivatives in high yield; subsequent diazotization and cyclization realised the 5-aryl-3-methylpyrazole[3,4-e],2,3,4]tetrazine derivatives. The structure of these novel, hetarylazo dyes was confirmed by UV-vis, FT-IR, and H-1 NMR spectroscopic techniques and elemental analysis. Optimal preparation conditions for 5-amino-4-phenylazo-3-methyl-1H-pyrazole were determined with respect to the effects of the AlCl3-catalyst, pH and temperature: the reaction mechanism of formation of the 5-aryl-3-methylpyrazole[3,4-e][1,2,3,4]tetrazines is discussed and the colours of the aminopyrazoles and pyrazolo-tetrazine dyes in a range of solvents are also discussed. (C) 2008 Published by Elsevier Ltd.
引用
收藏
页码：144 / 147
页数：4
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