Facile, selective, and regiocontrolled synthesis of oxazolines and oxazoles mediated by ZnI2 and FeCl3

Gopal Chandru Senadi; Wan-Ping Hu; Jia-Shing Hsiao; Jaya Kishore Vandavasi; Chung-Yu Chen; Jeh-Jeng Wang

doi:10.1021/ol301980g

Facile, selective, and regiocontrolled synthesis of oxazolines and oxazoles mediated by ZnI2 and FeCl3

Org Lett. 2012 Sep 7;14(17):4478-81. doi: 10.1021/ol301980g. Epub 2012 Aug 9.

Authors

Gopal Chandru Senadi¹, Wan-Ping Hu, Jia-Shing Hsiao, Jaya Kishore Vandavasi, Chung-Yu Chen, Jeh-Jeng Wang

Affiliation

¹ Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung, Taiwan.

PMID: 22876973
DOI: 10.1021/ol301980g

Abstract

An expedient method for a direct approach to the selective and regiocontrolled synthesis of 2-oxazolines and 2-oxazoles mediated by ZnI(2) and FeCl(3) is described. A Lewis acid promoted cyclization of acetylenic amide with various functionalities was well tolerated to give 2-oxazolines and 2-oxazoles in good to excellent yields under mild reaction conditions.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Chlorides / chemistry
Cyclization
Ferric Compounds / chemistry
Iodides / chemistry
Lewis Acids / chemistry
Molecular Structure
Oxazoles / chemical synthesis*
Oxazoles / chemistry
Zinc Compounds / chemistry

Substances

Chlorides
Ferric Compounds
Iodides
Lewis Acids
Oxazoles
Zinc Compounds
zinc iodide
ferric chloride