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Paper | Regular issue | Vol 36, No. 12, 1993, pp.2811-2818
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6525
Reaction of Trifluoroacetic Anhydride with N-(2-Hydroxybenzyl)-α-amino Acids: An Entry in the New [1,3]Oxazolo[2,3-b][1,3]benzoxazine Ring System

Bernard Chantegrel, Christian Deshayes,* and René Faure

*Laboratoire de Chimie Organique,Bâtiment 403, Institut National des Sciences Appliquées, Batiment 403, 20 Avenue Albert Einstein, 69621 Villeurbanne Cedex, France

Abstract

The diastereospecific double ring closure of N-(2-hydroxybenzyl)-α-amino acids with trifluoroacetic anhydride leads to the formation of 10a-trifluoromethyl-2,3,4,10a-tetrahydro[1,3]oxazolo[2,3-b][1,3]benzoxazin-2(5H)-ones. The chemical structures are supported by ir, 1H-nmr and 13 C-nmr spectra and X-ray analysis.