PIDA-mediated C-N coupling cyclization for the synthesis of 3-aryl-1H-indazoles

被引：0

作者：

Li, Na ^{[1
]}

Mo, Xiao-tian ^{[1
]}

Li, Zheng-yan ^{[1
]}

Zheng, Xing ^{[1
]}

Jiang, Lin ^{[1
]}

机构：

[1] Yunnan Minzu Univ, Sch Chem & Environm, Yunnan Key Lab Chiral Funct Subst Res & Applicat, Kunming 650504, Peoples R China

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2024年 / 60卷 / 9-10期

基金：

中国国家自然科学基金;

关键词：

hypervalent iodine reagent; indazole; vinylhydrazone; C-N coupling cyclization; oxidative aromatization; INDAZOLES; 1H-INDAZOLES; MILD;

D O I：

10.1007/s10593-024-03366-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of 6,7-dihydro-2H-indazoles by iodobenzene diacetate mediated intramolecular C-N coupling cyclization of acylhydrazones derived from (E)-2-methylidenecyclohex-3-enones was reported for the first time. Oxidative aromatization of these dihydroindazole intermediates with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone followed by in situ deprotection of the indazole nitrogen produced a series of 3-aryl-1H-indazoles in moderate to high yields. The cyclization method has the advantages of mild reaction conditions, broad substrate scope, and operational simplicity, which provides a novel synthetic route toward indazole derivatives and enriches the application of hypervalent iodine reagents in the synthesis of N-heterocyclic compounds.

引用

页码：480 / 490

页数：11