Proximity-assisted cycloaddition reactions of ω-azido cyanohydrin ethers: Synthesis of diversely functionalized bicyclic tetrazoles

被引：4
|
作者：
Hanessian, Stephen [1 ]
Deschenes-Simard, Benoit [1 ]
Simard, Daniel [1 ]
Chenel, Caroline [1 ]
Haak, Edgar [1 ]
Bulat, Vlad [1 ]
机构：
[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada
来源：
PURE AND APPLIED CHEMISTRY | 2010年 / 82卷 / 09期
基金：
加拿大自然科学与工程研究理事会;
关键词：
acetals; azides; cycloadditions; nitriles; tetrazoles; 1,3-DIPOLAR CYCLOADDITION; 5-SUBSTITUTED TETRAZOLES; CONFORMATIONAL MIMICRY; TRIMETHYLSILYL AZIDE; RHAMNO-FURANOSES; MALAYAMYCIN-A; CHEMISTRY; NITRILES; ACETALS; CONVERSION;
D O I：
10.1351/PAC-CON-09-08-08
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Aliphatic azidonitriles separated by three or four carbon atoms undergo facile cycloadditions in the presence of BF(3)center dot OEt(2) at room temperature or lower, to give bicyclic tetrazoles. 1-Azido-[2-aryl-1,3-dioxolanyl]-glycerols afford oxabicyclic tetrazoles with trimethylsilyl cyanide (TMSCN). Aspects of these facile proximity-induced 1,3-dipolar cycloadditions are discussed with mechanistic interpretations.
引用
收藏
页码：1761 / 1771
页数：11
相关论文
共 3 条
1