Specific features of the reactions of quinazoline and its 4-hydroxy and 4-chloro substituted derivatives with C-nucleophiles

被引：16
作者：
Azev, Yuri A. [1 ,2 ]
Shorshnev, Sergey V. [3 ]
Golomolzin, Boris V. [1 ]
机构：
[1] Ural Sci Res Inst Technol Med Preparat, Ekaterinburg 620219, Russia
[2] Ural State Tech Univ, Dept Chem, Ekaterinburg 620002, Russia
[3] Chembridge Corp, Moscow 119435, Russia
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 24期
关键词：
Quinazoline; Nucleophiles; Transformations;
D O I：
10.1016/j.tetlet.2009.03.199
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reactions of quinazoline 1 with indole, pyrogallol and 1-phenyl-3-methylpyrazol-5-one in the presence of acid led to C-4 adducts 2, 3 and 5. Adduct 4 is formed by heating I with 1,3-dimethylbarbituric acid without acid catalysis. 1-Phenyl-3-methylpyrazol-5-one reacts with 1 without acid catalysis to form dipyrazolylmethane 6. 4-Chloroquinazoline 8 reacts with 1-phenyl-3-methylpyrazol-5-one to form 4-(1-phenyl-3-methyl-5-oxopyrazol-4-yl) quinazoline 9 and dipyrazolylmethane 6. Heating 8 with 2-methylindole leads to the formation of 4-(2-methylindol-3-yl) quinazoline 10 and tris(2-methylindol-3-yl)methane 11. (C) 2009 Elsevier Ltd. All rights reserved.
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页码：2899 / 2903
页数：5
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