Microwave-assisted synthesis of 1-aryl-1H-indazoles via one-pot two-step Cu-catalyzed intramolecular N-arylation of arylhydrazones

被引：83
|
作者：
Pabba, C [1 ]
Wang, HJ [1 ]
Mulligan, SR [1 ]
Chen, ZJ [1 ]
Stark, TM [1 ]
Gregg, BT [1 ]
机构：
[1] Albany Mol Res Inc, Dept Med Chem, Albany, NY 12212 USA
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 44期
关键词：
1H-indazole; hydrazone; copper; cyclization; arylation; microwave irradiation;
D O I：
10.1016/j.tetlet.2005.08.143
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient one-pot two-step microwave procedure was developed for the synthesis of 1-aryl-1H-indazoles. Microwave heating of 2-halobenzaldehydes or 2-haloacetophenones with phenylhydrazines at 160 degrees C for 10 min quantitatively yielded the arylhydrazones, which were further cyclized to give 1-aryl-1H-indazoles via CuI/diamine-catalyzed N-arylation under microwave heating (160 degrees C, 10min). Good to excellent yields were observed for 2-iodo, 2-bromo, and 2-chloro benzaldehydes or acetophenones. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7553 / 7557
页数：5
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