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Synlett 1996; 1996(11): 1129-1130
DOI: 10.1055/s-1996-5675
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Di-tert-Butyl Pyrocarbonate Mediated Cyclodehydration of N-Acyl Amino Acids into Functionalized Oxazoles and Acylanthranils#

Debendra K. Mohapatra, Apurba Datta*
  • *Organic III, Indian Institute of Chemical Technology, Hyderabad - 500 007, India
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Publication Date:
31 December 2000 (online)

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Di-tert-butyl pyrocarbonate, on reaction with N-acyl amino acids, was found to serve the dual purpose of i) initial carboxylic acid activation-tandem cyclization through the amide carbonyl, and ii) trapping of the enol moiety thus formed, leading to a mild and efficient one-pot synthesis of 5-tert-butoxycarbonyloxy substituted oxazoles. N-Acyl anthranilic acids under similar reaction conditions afforded acylanthranils in high yields.

di-tert-butylpyrocarbonate - cyclodehydration - oxazole - acylanthranil