An efficient, facile, and general synthesis of 1H-indazoles by 1,3-dipolar cycloaddition of arynes with diazomethane derivatives

被引:154
作者
Jin, Tienan [1 ]
Yamamoto, Yoshinori [1 ]
机构
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
关键词
1,3-dipolar cycloaddition; arynes; diazo compounds; heterocycles; indazoles;
D O I
10.1002/anie.200700101
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Take your pick: Both N-unsubstituted and 1-aryl 1H-indazoles are available in good to high yields through the [3+2] cycloaddition of benzynes derived from o-silylaryl triflates with diazomethane derivatives (see scheme). In the presence of KF/[18]crown-6, the N-unsubstituted 1H-indazole is formed, whereas the 1-arylated product is obtained regioselectively with CsF and an excess of the triflate. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3323 / 3325
页数:3
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