Synthesis of Substituted 1H-Indazoles from Arynes and Hydrazones

被引：83

作者：

Li, Pan ^{[1
]}

Wu, Chunrui ^{[1
]}

Zhao, Jingjing ^{[1
]}

Rogness, Donald C. ^{[2
]}

Shi, Feng ^{[1
]}

机构：

[1] Henan Univ, Key Lab Nat Med & Immunoengn Henan Prov, Kaifeng 475004, Henan, Peoples R China

[2] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 07期

基金：

中国国家自然科学基金;

关键词：

1,3-DIPOLAR CYCLOADDITION; DIAZO-COMPOUNDS; 3-SUBSTITUTED INDAZOLES; TOSYLHYDRAZONE SALTS; EFFICIENT SYNTHESIS; CARBONYL-COMPOUNDS; GENERAL-SYNTHESIS; NITRILE IMINES; INSERTION; DERIVATIVES;

D O I：

10.1021/jo202598e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1H-indazole skeleton can be constructed by a [3 + 2] annulation approach from arynes and hydrazones. Under different reaction conditions, both N-tosylhydrazones and N-aryl/alkylhydrazones can be used to afford a variety of indazoles. The former reaction affords 3-substituted indazoles either via in situ generated diazo compounds or through an annulation/elimination process. The latter reaction leads to 1,3-disubstituted indazoles likely through an annulation/oxidation process. The reactions operate under mild conditions and can accommodate aryl, vinyl, and less satisfactorily, alkyl groups.

引用

页码：3149 / 3158

页数：10

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