Application of primary halogenated hydrocarbons for the synthesis of 3-aryl and 3-alkyl indolizines. Issue 23 (1st June 2017)

• Record Type: Journal Article
• Authors: Liu, Yan; Hu, Huayou; Zhou, Junyu; Wang, Wenhui; He, Youliang; Wang, Chao
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 23(2017)
• Page Start: 5016
• Page End: 5024
• Publication Date: 2017-06-01
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob00980a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A transition-metal-free synthetic route to 3-aryl and 3-alkyl indolizines from electron-deficient alkenes, pyridines and primary halogenated hydrocarbons is reported for the first time using a tandem reaction. Abstract : 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.