Chemistry of Heterocyclic Compounds

, Volume 27, Issue 8, pp 903–907 | Cite as

2-Carbethoxy-4H-3,1-benzoxazin-4-one. 1. Synthesis and reaction mechanism of formation

  • I. V. Ukrainets
  • P. A. Bezuglyi
  • V. I. Treskach
  • S. V. Slobodzyan


The possibility was examined of using various condensing agents in the intramolecular cyclization reaction of ethyl ester of 2-carbomalonanilic acid into 2-carboethoxymethyl-4H-3,1-benzoxazin-4-one. It was found that the optimal reagent is dicyclohexylcarbodiimide. By using NMR spectroscopy and deutero-exchange it was shown that the cyclization proceeds with the participation of the hydroxyl group of the carboxyl and a proton of the amide function.


Spectroscopy Ester Ethyl Hydroxyl Organic Chemistry 
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Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • I. V. Ukrainets
    • 1
  • P. A. Bezuglyi
    • 1
  • V. I. Treskach
    • 1
  • S. V. Slobodzyan
    • 1
  1. 1.Khar'kov Pharmaceutical InstituteKhar'kov

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