HETEROCYCLIC IONS FROM N-OXIDES OF N-(4-NITROBENZYLIDENE)-2-CYCLOPROPYLANILINE AND N-(4-NITROBENZYLIDENE)-2-CYCLOPROPYLMETHYLANILINE: FORMATION, ISOMERIZATION, AND CONVERSIONS

Authors

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

Keywords:

o-(2-hydroxyalkyl)anilines, heterocyclic ions, N-oxides of N-(4-nitrobenzylidene)-2-cyclopropylanilines, 2,1-benzoxazinium salts, 2,1-benzoxazepinium salts, isomerization

Abstract

The N-oxide of N-(4-nitrobenzylidene)-2-cyclopropylaniline is converted by the action of strong acids into the corresponding 2,1-benzoxazinium derivative. Under identical conditions the N-oxide of N-(4-nitrobenzylidene)-2-cyclopropylmethylaniline forms the corresponding 2,1-benzoxazinium and 2,1-benzoxazepinium salts in a ratio of 1 : 2. The 2,1-benzoxazepinium ions are thermodynamically less stable and are isomerized with time into 2,1-benzoxazinium ions. Treatment of 2,1-benzoxazinium salts with hydrobromic acid solution and subsequent neutralization leads to o-(2-hydroxyalkyl)anilines and p-nitrobenzaldehyde. The effect of the nature of the ortho substituent on the direction of the conversions of the corresponding arylcyclopropanes is discussed.

How to Cite
Trofimova, E. V.; Fedotov, A. N.; Gazzaeva, R. A.; Mochalov, S. S.; Shabarov, Yu. S.; Zefirov, N. S. Chem. Heterocycl. Compd. 2003, 39, 205. [Khim. Geterotsikl. Soedin. 2003, 234.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1023720525095

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Published

2003-02-25

Issue

No. 2 (2003)

Section

Original Papers