Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Tuesday 19th September 2017 from 8.00am to 4.00pm (BST).

During this time our website performance may be temporarily affected. If you have any questions please use the feedback button available under our menu button. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 23, 2017
Previous Article Next Article

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

Author affiliations

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.

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 21 Apr 2017, accepted on 18 May 2017 and first published on 18 May 2017


Article type: Paper
DOI: 10.1039/C7OB00980A
Citation: Org. Biomol. Chem., 2017,15, 5016-5024
  •   Request permissions

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

    Y. Liu, H. Hu, J. Zhou, W. Wang, Y. He and C. Wang, Org. Biomol. Chem., 2017, 15, 5016
    DOI: 10.1039/C7OB00980A

Search articles by author

Spotlight

Advertisements