<i>N</i>-ACYLAMINOPHENYLCYCLOPROPANES IN REACTION WITH NITROUS ACID GENERATED <i>in situ</i>

Authors

  • С. С. Мочалов Moscow M. V. Lomonosov State University
  • Р. А. Газзаева North-Ossetiian K. L. Khetagurov State University
  • А. З. Каджаева Moscow M. V. Lomonosov State University
  • А. Н. Федотов Moscow M. V. Lomonosov State University
  • Е. В. Трофимова Moscow M. V. Lomonosov State University

DOI:

https://doi.org/10.1007/1352

Keywords:

N-acylaminophenylcyclopropanes, 3, 1-benzoxazines, Δ2-isoxazolines, heterocyclization

Abstract

The reaction of N-acylaminophenylcyclopropanes with HNO2 proceeds regioselectively with introduction of an N=O fragment into the three-membered ring and formation of the corresponding Δ2-isoxazolines. For ortho-substituted N-acylaminophenylcyclopropanes side processes were observed, caused by the intramolecular participation of the N-acyl group in conversions of the carbenium ions formed on opening the cyclopropane ring under the action of the nitrosating reagent, and by direct insertion of the modified ortho substituent into the three-membered ring.

Authors: S. S. Mochalov, R. A. Gazzaeva, A. Z. Kadzhaeva, A. N. Fedotov, and E. V. Trofimova.

English translation in Chemistry of Heterocyclic Compounds, 2011, 47 (11), pp 1415-1429

http://link.springer.com/article/10.1007/s10593-012-0929-y

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Published

2013-12-12

Issue

No. 11 (2011)

Section

Original Papers