Heterocyclization of N-(chlorosulfonyl)imidoyl chlorides with anilines, a new method of synthesis of 1,2,4-benzothiadiazine 1,1-dioxides

被引:0
作者
Alexander A. Shalimov
Tetyana I. Chudakova
Yurii G. Vlasenko
Anatoly D. Sinitsa
Petro P. Onys’ko
机构
[1] National Academy of Sciences of Ukraine,Institute of Organic Chemistry
来源
Chemistry of Heterocyclic Compounds | 2016年 / 52卷
关键词
anilines; 1,2,4-benzothiadiazine 1,1-dioxides; imidoyl chlorides; sulfonyl chlorides; heterocyclization;
D O I
暂无
中图分类号
学科分类号
摘要
N-(Chlorosulfonyl)imidoyl chlorides react regioselectively with anilines, 2-aminomethylnaphthaline, or 1,2,3,4-tetrahydroquinoline leading to derivatives of 1,2,4-benzothiadiazine 1,1-dioxide. Heterocyclization occurs at the sterically less hindered C-6 atom in the case of 3-methoxy- and 3,4-dimethoxyaniline, while the reaction with 3-methylaniline leads to a mixture of cyclization products at the C-2 and C-6 atoms of aniline.
引用
收藏
页码:267 / 274
页数:7
相关论文
共 89 条
[1]  
Tedesco R(2006)undefined J. Med. Chem. 49 971-undefined
[2]  
Shaw AN(2009)undefined Bioorg. Med. Chem. Lett. 19 6404-undefined
[3]  
Bambal R(1973)undefined Farmaco 28 149-undefined
[4]  
Chai D(2005)undefined Aust. J. Chem. 58 332-undefined
[5]  
Concha NO(2008)undefined Aust. J. Chem. 61 785-undefined
[6]  
Darcy MG(2007)undefined J. Aust. J. Chem. 60 113-undefined
[7]  
Dhanak D(2005)undefined J. Aust. J. Chem. 58 891-undefined
[8]  
Fitch DM(2013)undefined Aust. J. Chem. 66 1323-undefined
[9]  
Gates A(1988)undefined J. Prakt. Chem. 330 900-undefined
[10]  
Gerhardt WG(1970)undefined Chem. Ind. 1 27-undefined