Regioselective 1,3-Dipolar Cycloaddition of Nitriles with Nitrile Imines Generated from Tetrazoles

被引：5
|
作者：
Miura, Tomoya [1 ]
Hagiwara, Kohei [1 ]
Nakamuro, Takayuki [1 ,3 ]
Nagata, Yuuya [2 ]
Oku, Naoki [1 ]
Murakami, Masahiro [1 ]
机构：
[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
[2] Hokkaido Univ, Inst Chem React Design & Discovery WPI ICReDD, Sapporo, Hokkaido 0010021, Japan
[3] Univ Tokyo, Dept Chem, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan
来源：
CHEMISTRY LETTERS | 2021年 / 50卷 / 01期
关键词：
Cycloaddition; Nitrile imines; Tetrazoles; COPPER-CATALYZED SYNTHESIS; 1.3-DIPOLARE CYCLOADDITIONEN; THERMAL-DECOMPOSITION; 1,2,4-TRIAZOLES; REACTIVITY; ISOCYANIDES; PYRAZOLINES; ACCESS;
D O I：
10.1246/cl.200634
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A synthesis of 3,5-disubstituted-1,2,4-triazoles from nitriles and 5-aryltetrazoles is reported. When 5-aryltetrazoles are triflylated in the presence of nitriles, the resulting 5-aryl-2-triflyltetrazoles thermally generate N-triflyl-nitrile imines through a sequence of ring-chain tautomerization and denitrogenation. The N-triflyl-nitrile imines immediately undergo 1,3dipolar cycloaddition with nitriles in a regioselective manner, forming the corresponding 1,2,4-triazoles.
引用
收藏
页码：131 / 135
页数：5
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