NEW PATHWAY TO THE SYNTHESIS OF SUBSTITUTED 4H-3,1-BENZOXAZINES

Authors

  • С. С. Мочалов M. V. Lomonosov Moscow State University, 119234 Moscow
  • Р. А. Газзаева M. V. Lomonosov Moscow State University, 119234 Moscow
  • А. Н. Федотов M. V. Lomonosov Moscow State University, 119234 Moscow
  • Ю. С. Шабаров M. V. Lomonosov Moscow State University, 119234 Moscow
  • Н. С. Зефиров M. V. Lomonosov Moscow State University, 119234 Moscow

Keywords:

N-acylamino-2-alkenylbenzenes, N-acyl-2-cyclopropylanilines, 4H-3,1-benzoxazines, 4H-3,1-benzoxazinium ions, rearrangement

Abstract

he intramolecular rearrangement of N-acyl-2-cyclopropylanilines by the action of protic acids gives substituted 4H-3,1-benzoxazines. The reaction proceeds in high yield through the formation of benzoxazine precursors, namely, the corresponding 3,1-benzoxazinium ions, which are stable in acid solution. N-Acylamino-2-alkenylbenzenes, in which the double bond of the alkyl chain is conjugated with the benzene ring, are capable of undergoing a similar rearrangement.

How to Cite
Mochalov, S. S.; Gazzaeva, R. A.; Fedotov, A. N.; Shabarov, Yu. S.; Zefirov, N. S. Chem. Heterocycl. Compd. 2003, 39, 794. [Khim. Geterotsikl. Soedin. 2003, 922.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1025611632368

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Published

2003-06-25

Issue

No. 6 (2003)

Section

Original Papers