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Synthesis of 3-Alkylbenzoxazolones from N-Alkyl-N-arylhydroxylamines by Contiguous O-Trichloroacetylation, Trichloroacetoxy ortho-Shift, and Cyclization Sequence

Ram N. Ram* and Vineet Kumar Soni

*Department of Chemistry, Indian Institute of Technology, Delhi, Hauz Khas, New Delhi 110016, India, Email: rnramchemistry.iitd.ac.in

R. N. Ram. V. K. Soni, J. Org. Chem., 2013, 78, 11935-11947.

DOI: 10.1021/jo401985h (free Supporting Information)


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Abstract

Benzoxazolone pharmacophore is present in many compounds having a wide spectrum of biological activities. Treatment of N-alkyl-N-arylhydroxylamines with trichloroacetyl chloride and triethylamine afforded 3-alkylbenzoxazolones generally in good yields at ambient temperatures. The present method is mild, wide in scope, economical, and regioselective. Many sensitive groups are tolerated.

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Key Words

benzoxazolones


ID: J42-Y2013