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Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles

Phongprapan Nimnual, Jumreang Tummatorn*, Charnsak Thongsornkleeb and Somsak Ruchirawat

*Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand, Email: jumreangcri.or.th

P. Nimnual, J. Tummatorn, C. Thongsornkleeb, S. Ruchirawat, J. Org. Chem., 2015, 80, 8657-8667.

DOI: 10.1021/acs.joc.5b01305 (free Supporting Information)


 

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Abstract

Nitrogen extrusion reactions of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, enable the synthesis of benzisoxazole, nitriles, benzoxazoles depending on the substrates.

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Key Words

benzoxazoles


ID: J42-Y2015