Tandem synthesis of 3-halo-5-substituted isoxazoles from 1-copper(I) alkynes and dihaloformaldoximes

Wenwen Chen; Bo Wang; Nan Liu; Dayun Huang; Xinyan Wang; Yuefei Hu

doi:10.1021/ol503008t

Tandem synthesis of 3-halo-5-substituted isoxazoles from 1-copper(I) alkynes and dihaloformaldoximes

Org Lett. 2014 Dec 5;16(23):6140-3. doi: 10.1021/ol503008t. Epub 2014 Nov 14.

Authors

Wenwen Chen¹, Bo Wang¹, Nan Liu¹, Dayun Huang¹, Xinyan Wang¹, Yuefei Hu¹

Affiliation

¹ Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.

PMID: 25397915
DOI: 10.1021/ol503008t

Abstract

A tandem synthesis of 3-halo-5-substituted isoxazoles has been developed from 1-copper(I) alkynes and dihaloformaldoximes under base-free conditions. Thus, 1,3-dipolar cycloaddition and all its drawbacks can now be avoided completely.

Publication types

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

MeSH terms

Alkynes / chemistry*
Catalysis
Copper / chemistry*
Cyclization
Hydrocarbons, Brominated / chemical synthesis*
Hydrocarbons, Brominated / chemistry*
Isoxazoles / chemical synthesis*
Isoxazoles / chemistry
Molecular Structure
Oximes / chemistry*

Substances

Alkynes
Hydrocarbons, Brominated
Isoxazoles
Oximes
formaldoxime
Copper