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

页码：144 / 147

页数：4

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