An improved synthesis of 1,2-benzisoxazoles: TBAF mediated 1,3-dipolar cycloaddition of nitrile oxides and benzyne

Christian Spiteri; Pallavi Sharma; Fengzhi Zhang; Simon J F Macdonald; Steve Keeling; John E Moses

doi:10.1039/b922489k

An improved synthesis of 1,2-benzisoxazoles: TBAF mediated 1,3-dipolar cycloaddition of nitrile oxides and benzyne

Chem Commun (Camb). 2010 Feb 28;46(8):1272-4. doi: 10.1039/b922489k. Epub 2010 Jan 11.

Authors

Christian Spiteri¹, Pallavi Sharma, Fengzhi Zhang, Simon J F Macdonald, Steve Keeling, John E Moses

Affiliation

¹ School of Chemistry, University of Nottingham, University Park, Nottingham, UK NG7 2RD.

PMID: 20449274
DOI: 10.1039/b922489k

Abstract

An efficient synthesis of a range of 1,2-benzisoxazoles using an improved 1,3-dipolar cycloaddition of nitrile oxides and benzyne is described. Key to the procedure is the in situ generation of the reactive nitrile oxide and benzyne reaction partners mediated by TBAF. Reactions are complete within 30 s, giving the target products in good to excellent yield.

Publication types

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

MeSH terms

Benzene Derivatives / chemical synthesis
Benzene Derivatives / chemistry*
Catalysis
Cyclization
Isoxazoles / chemical synthesis*
Isoxazoles / chemistry
Nitriles / chemical synthesis
Nitriles / chemistry*
Oxides / chemical synthesis
Oxides / chemistry

Substances

1,2-benzisoxazole
Benzene Derivatives
Isoxazoles
Nitriles
Oxides
benzyne