Work

Synthesis of Dihydrobenzisoxazoles by the [3 + 2] Cycloaddition of Arynes and Oxaziridines

Year: 2010

Type: article

Abstract: Dihydrobenzisoxazoles are readily prepared in good yields by the [3 + 2] cycloaddition of oxaziridines and arynes. The reaction involves an unusual cleavage of the C-O bond of the oxaziridine and tolerates a variety of substituents on the oxaziridine and the o-(trimethylsilyl)aryl triflate to form aryl-, heteroaryl-, alkyl-, and naphthyl-substituted dihydrobenzisoxazoles. The resulting halogen-substituted dihydrobenzisoxazoles are readily elaborated to more complex products using palladium-catalyzed crossing-coupling processes.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo101656c

Authors: Arif Kivrak, Richard C. Larock

Institutions: Iowa State University, Middle East Technical University

Language: English

Topic: Cyclization and Aryne Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: Center of Excellence in Chemical Methodologies and Library Development, Pilot-Scale Heterocyclic and Carbocyclic Libraries for High Throughout Screening, Synthesis of Medicinally Important Heterocycles