Assembly of Substituted 3‑Aminoindazoles from 2‑Bromobenzonitrile via a CuBr-Catalyzed Coupling/Condensation Cascade Process

CuBr-catalyzed coupling reaction of 2-halobenzonitriles with hydrazine carboxylic esters and CuBr/4-hydroxy-l-proline-catalyzed coupling reaction of 2-bromobenzonitriles with N′-arylbenzohydrazides proceed smoothly at 60–90 °C to provide substituted 3-aminoindazoles through a cascade coupling/conden...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-04, Vol.78 (7), p.3400-3404
Main Authors: Xu, Lanting, Peng, Yinsheng, Pan, Qiangbiao, Jiang, Yongwen, Ma, Dawei
Format: Article
Language:English
Subjects:
Bromides - chemistry
Catalysis
Copper - chemistry
Indazoles - chemical synthesis
Indazoles - chemistry
Molecular Structure
Nitriles - chemistry
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Summary:CuBr-catalyzed coupling reaction of 2-halobenzonitriles with hydrazine carboxylic esters and CuBr/4-hydroxy-l-proline-catalyzed coupling reaction of 2-bromobenzonitriles with N′-arylbenzohydrazides proceed smoothly at 60–90 °C to provide substituted 3-aminoindazoles through a cascade coupling/condensation (or coupling/deacylation/condensation) process. A wide range of 3-aminoindazoles with substituents at both the 1-position and the phenyl ring part can be prepared from the corresponding coupling partners.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo400071h