4H-3,1-BENZOXAZINES FROM BENZYL CYCLOPROPANES. FIRST EXAMPLE OF ACID CATALYZED REARRANGEMENT IN <i>ortho</i>-SUBSTITUTED BENZYLCYCLOPROPANES

Authors

  • Е. В. Трофимова Moscow M. V. Lomonosov State University, Moscow 119992
  • Б. П. Арчегов Moscow M. V. Lomonosov State University, Moscow 119992
  • А. Н. Федотов Moscow M. V. Lomonosov State University, Moscow 119992
  • Р. А. Газзаева Moscow M. V. Lomonosov State University, Moscow 119992
  • С. С. Мочалов Moscow M. V. Lomonosov State University, Moscow 119992
  • Н. С. Зефиров Moscow M. V. Lomonosov State University, Moscow 119992

DOI:

https://doi.org/10.1007/6587

Keywords:

4-alkyl-4H-3, 1-benzoxazines, 6-allyl-7-amino-1, 4-benzodioxane, 2-aminobenzylcyclopropanes, 2-N-acylaminoallylbenzenes, 2-N-acylaminobenzylcyclopropanes, 6-butyroyl-7-nitro-1, 1-(2-N-p-methoxybenzoylamino)-4, 5-ethylenedioxyphenylbutan-1-ol, 2-nitrobenzylcyclopropanes, rearrangements

Abstract

The synthesis of 2-N-acylamino-substituted benzylcyclopropanes has been carried out. It was established that under the action of acids 2-N-acylamino-substituted benzylcyclopropanes are rearranged into the corresponding 4H-3,1-benzoxazines and not into the expected 3,1-benzoxazepines. It was shown that a similar type of rearrangement is also characteristic for 2-N-acylamino-substituted allylbenzenes.

How to Cite
Trofimova, E. V.; Archegov, B. P.; Fedotov, A. N.; Gazzaeva, R. A.;  Mochalov, S. S.; Zefirov, N. S.Chem. Heterocycl. Compd. 2009, 45, 1095. [Khim. Geterotsikl. Soedin. 2009, 1368.]

For this article in the English edition see DOI 10.1007/s10593-009-0400-x

 

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Published

2022-02-14

Issue

No. 9 (2009)

Section

Original Papers