Synthesis of 3-substituted indazoles and benzoisoxazoles via Pd-catalyzed cyclization reactions: application to the synthesis of nigellicine

被引:88
作者
Inamoto, Kiyofumi [1 ]
Katsuno, Mika
Yoshino, Takashi
Arai, Yukari
Hiroya, Kou
Sakamoto, Takao
机构
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, 21st Century COE Program, Comprehens Res & Educ Ctr Planning Drug Dev & Cli, Sendai, Miyagi 9808578, Japan
关键词
palladium; animation; hydrazone; indazole; benzoisoxazole; nigellicine;
D O I
10.1016/j.tet.2007.01.010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Syntheses of 3-substituted indazoles and benzoisoxazoles were efficiently accomplished with the aid of Pd-catalyzed intramolecular carbon-nitrogen and carbon-oxygen bond formations. The catalyst system described herein allows the cyclization to proceed under very mild conditions and thus could be applied to a wide range of substrates with acid- or base-sensitive functional groups. A total synthesis for the indazole ring-containing natural product nigellicine is also described. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2695 / 2711
页数:17
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