Chemoselective Aza-[4+3]-annulation of N-Perfluoroalkyl-1,2,3-triazoles with 1,3-Dienes: Access to N-Perfluoroalkyl-Substituted Azepines

被引：41
作者：
Motornov, Vladimir [1 ,2 ]
Beier, Petr [1 ]
机构：
[1] Czech Acad Sci, Inst Organ Chem & Biochem, Flemingovo Nam 2, Prague 16610 6, Czech Republic
[2] DI Mendeleev Univ Chem Technol Russia, Higher Chem Coll, Miusskaya Sq 9, Moscow 125047, Russia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 24期
关键词：
RHODIUM-CATALYZED TRANSANNULATION; 1,2,3-TRIAZOLES; REARRANGEMENT; GENERATION; ANNULATION; FLUORINE; ALKYNES; AZIDES;
D O I：
10.1021/acs.joc.8b02472
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Rhodium-catalyzed transannulation of N-perfluoroalkylated 1,2,3-triazoles with 1,3-dienes under microwave heating proceeded chemoselectively via the formal aza-[4+3]-pathway, affording N-perfluoroalkyl-substituted 2,5-dihydroazepines. A unique regioselectivity profile was observed in annulation with 1-substituted 1,3-diene, affording unusual 5,6-disubstituted examples. Transannulation of triazoles with 2-trimethylsilyloxybutadiene provided N-perfluoroalkyl-substituted azepinone derivatives.
引用
收藏
页码：15195 / 15201
页数：7
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