One-pot synthesis of N-substituted benzannulated triazoles via stable arene diazonium salts

被引：7
|
作者：
McGrory, Rochelle [1 ]
Faggyas, Reka J. [1 ]
Sutherland, Andrew [1 ]
机构：
[1] Univ Glasgow, Sch Chem, Joseph Black Bldg, Glasgow G12 8QQ, Lanark, Scotland
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 27期
关键词：
CATALYZED DENITROGENATIVE ANNULATION; TERT-BUTYL NITRITE; ALPHA-AMINO-ACIDS; SELECTIVE SYNTHESIS; ALKYNE INSERTION; 1,2,3-BENZOTRIAZIN-4(3H)-ONES; 1,2,3-BENZOTRIAZINE-4-(3H)-ONES; 2-AMINOBENZAMIDES; BENZOTRIAZINONE; SULFONAMIDES;
D O I：
10.1039/d1ob00968k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamides via stable diazonium salts, prepared using a polymer-supported nitrite reagent and p-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton-cyclisation process was further demonstrated with the preparation of an alpha-amino acid containing 1,2,3-benzotriazin-4(3H)-one.
引用
收藏
页码：6127 / 6140
页数：14
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