Direct Formation of 2-Substituted 2H-Indazoles by a Pd-Catalyzed Reaction between 2-Halobenzyl Halides and Arylhydrazines

被引：19

作者：

Aljaar, Nayyef ^{[1
]}

Al-Noaimi, Mousa ^{[1
]}

Conrad, Juergen ^{[2
]}

Beifuss, Uwe ^{[2
]}

机构：

[1] Hashemite Univ, Fac Sci, Dept Chem, Zarqa 13133, Jordan

[2] Univ Hohenheim, Inst Chem, Bioorgan Chem, D-70599 Stuttgart, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 02期

关键词：

EFFICIENT SYNTHESIS; INTRAMOLECULAR AMINATION; FACILE; 1-ARYL-1H-INDAZOLES; 2-ARYL-2H-INDAZOLES; CONDENSATION; CYCLIZATION; DISCOVERY; INDAZOLES; DESIGN;

D O I：

10.1021/acs.joc.0c01923

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct and operationally simple method for the regioselective synthesis of 2-aryl-substituted 2H-indazoles is reported. The Pd-catalyzed reaction between easily available 2-bromobenzyl bromides and arylhydrazines employing Cs2CO3 as the base and t-Bu3PHBF4 as the ligand in DMSO at 120 degrees C in a sealed tube delivers the 2-substituted-2H-indazoles in a single synthetic step with yields up to 79%. The new method is based on a regioselective intermolecular N-benzylation followed by intramolecular N-arylation and oxidation.

引用

页码：1408 / 1418

页数：11

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