Synthesis of 5-substituted 1H-tetrazoles by the copper-catalyzed [3+2] cycloaddition of nitriles and trimethylsilyl azide

被引:51
|
作者
Jin, Tienan [1 ]
Kitahara, Fukuzou [1 ]
Kamijo, Shin [2 ]
Yamamoto, Yoshinori [1 ]
机构
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan
[2] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
copper; cycloaddition; homogeneous catalysis; nitriles; tetrazoles;
D O I
10.1002/asia.200800085
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The copper-catalyzed [3+2] cycloaddition between various nitriles and trimethylsilyl azide in DMF/MeOH produced the corresponding 5-substituted 1H-tetrazoles in good to high yields. It was proposed that the reaction proceeds through the formation in situ of a copper azide species and subsequent [3+2] cycloaddition with the nitriles. Furthermore, we found that a copper and triethylamine combined catalyst also promoted the cycloaddition of nitriles and trimethylsilyl azide to afford the 5-substituted 1H-tetrazoles at relatively low reaction temperatures. The copper azide species would be formed by reaction of the copper catalyst with Et3N center dot HN3 generated in situ.
引用
收藏
页码:1575 / 1580
页数:6
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