Application of primary halogenated hydrocarbons for the synthesis of 3-aryl and 3-alkyl indolizines

作者：Liu, Yan; Hu, Huayou^*; Zhou, Junyu; Wang, Wenhui; He, Youliang; Wang, Chao^*

来源：Organic and Biomolecular Chemistry, 2017, 15(23): 5016-5024.

DOI：10.1039/c7ob00980a

• ELECTRON-DEFICIENT ALKENES
• 5-HT3 RECEPTOR ANTAGONISTS
• POTENT INHIBITORS
• 1,3-DIPOLAR CYCLOADDITION
• OXIDATIVE ANNULATION
• QUINOLIZIDINE ALKALOIDS
• DERIVATIVES
• OXIDANT
• FLUORESCENT
• ANALOGS

Indolizine is an important heterocyclic compound with several interesting properties that make it suitable for numerous applications in many fields, such as biology, medicine and materials. However, the synthesis of 3-alkyl indolizines from bulky primary halogenated alkanes has not yet been reported. Herein, a transition-metal-free synthetic route to 3-aryl and 3-alkyl indolizines from electron-deficient alkenes, pyridines and primary halogenated hydrocarbons has been reported for the first time using a tandem reaction. The key step of this method is the oxidative dehydrogenative aromatization of a tetrahydroindolizine intermediate with 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) as the oxidant. The advantages of this protocol are its use of easily available and low-cost starting materials, the transition-metal-free conditions and its ready scalability.

• 出版日期2017-6-21
• 单位西南科技大学; 淮阴师范学院; 南京大学