REACTION OF THE N-MESYLATES OF 1,3a,4,8b-TETRAHYDROCYCLOPENTA[<i>b</i>]INDOLES AND 3,4,4a,9a-TETRAHYDROCARBAZOLES WITH DIMETHYLDIOXIRANE AND BROMINE

Authors

  • Р. Р. Гатауллин Institute of Organic Chemistry, Ufa Science Center of the Russian Academy of Sciences, Ufa 450054
  • Р. Р. Ишбердина Bashkir State Agrarian University, Department of General Chemistry, Ufa 450003
  • А. В. Антипин Institute of Organic Chemistry, Ufa Science Center of the Russian Academy of Sciences, Ufa 450054
  • К. Ю. Супоницкий N. A. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow 117813
  • Н. Н. Кабальнова Institute of Organic Chemistry, Ufa Science Center of the Russian Academy of Sciences, Ufa 450054
  • О. В. Шитикова Institute of Organic Chemistry, Ufa Science Center of the Russian Academy of Sciences, Ufa 450054
  • Л. В. Спирихин Institute of Organic Chemistry, Ufa Science Center of the Russian Academy of Sciences, Ufa 450054
  • М. Ю. Антипин N. A. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow 117813
  • И. Б. Абдрахманов Institute of Organic Chemistry, Ufa Science Center of the Russian Academy of Sciences, Ufa 450054

DOI:

https://doi.org/10.1007/7808

Keywords:

dimethyldioxirane, tetrahydrocarbazoles, tetrahydrocyclopenta[b]indoles, X-ray crystallographic analysis

Abstract

In reaction with dimethyldioxirane N-mesyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles and N-mesyl-3,3,4a,9a-tetrahydrocarbazoles mostly form the trans-epoxide. The reaction with molecular bromine leads to the product from halogenation in the aromatic ring, i.e., the corresponding N-mesyl-7-bromo-1,3a,4,8b-tetrahydrocyclopenta[b]indole or N-mesyl-6-bromo-3,4,4a,9a-tetrahydrocarbazole.

How to Cite
Gataullin, R. R.; Ishberdina, R. R.; Antipin, A. V.; Suponitskii, K. Yu.; Kabal'nova, N. N.; Shitikova, O. V.; Spirikhin, L. V.;  Antipin, M. Yu.; Abdrakhmanov, I. B.  Chem. Heterocycl. Compd. 2006, 42, 1130. [Khim. Geterotsikl. Soedin. 2006, 1306.]

For this article in the English edition see DOI 10.1007/s10593-006-0216-x


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Published

2023-05-18

Issue

No. 9 (2006)

Section

Original Papers