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.
Similar content being viewed by others
References
J. A. Murphy, K. A. Scot, R. S. Sinclan, and N. Lewis, Tetrahedron Lett., 38, 7295 (1997).
J. A. Murphy, F. Rasheed, S. Gastraldi, T. Ravishander, and N. Lewis, J. Chem. Soc., Perkin Trans. 1, 1549 (1997).
R. R. Gataullin, F. F. Minnigulov, A. A. Fatykhov, L. V. Spirikhin, and I. B. Abdrakhmanov, Zh. Org. Khim., 37, 1357 (2001).
R. R. Gataullin, R. R. Ishberdina, O. V. Shitikova, F. F. Minnigulov, L. V. Spirikhin, and I. B. Abdrakhmanov, Khim. Geterotsikl. Soedin., 1184 (2006). [Chem. Heterocycl. Comp., 42, 1025 (2006)].
E. Pretsch, T. Clerk, J. Seible, and W. Simon, Tables of Spectral Data for Structure Determination of Organic Compounds, Springer Verlag, Berlin, Heidelberg, New York, Tokyo, 730 (1983).
SMART and SAINT, Release 5.0, Area Detector Control and Integration Software, Bruker AXS, Analytical X-ray Instruments, Madison, Wisconsin, USA (1998).
G. M. Sheldrick, SADABS: A Program for Exploiting the Redundancy of Area-Detector X-ray Data, Univ. of Göttingen, Göttingen, Germany (1999).
G.M. Sheldrick, SHELXTL-97. Program for Solution and Refinement of Crystal Structure, Bruker AXS Inc., Madison, WI-53719, USA (1997).
Author information
Authors and Affiliations
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1306–1313, September, 2006.
Rights and permissions
About this article
Cite this article
Gataullin, R.R., Ishberdina, R.R., Antipin, A.V. et al. Reaction of the N-mesylates of 1,3a,4,8b-tetrahydrocyclopenta[b]indoles and 3,4,4a,9a-tetrahydrocarbazoles with dimethyldioxirane and bromine. Chem Heterocycl Compd 42, 1130–1136 (2006). https://doi.org/10.1007/s10593-006-0216-x
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10593-006-0216-x