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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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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