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New synthesis of 9-methanesulfonyl-1,2,3,9a-tetrahydro- and 1,2,3,4-tetrahydrocarbazoles from N-methanesulfonyl-2-(cyclohex-1-enyl)aniline

Rail Rafkatovich Gataullin 1
Rail Rafkatovich Gataullin
, 
Alexander Mikhailovich Sotnikov 1
Alexander Mikhailovich Sotnikov
, 
Ildus Barievich Abdrakhmanov 1
Ildus Barievich Abdrakhmanov
, 
Genrikh Alexandrovich Tolstikov 1
Genrikh Alexandrovich Tolstikov
10.1070/MC2003v013n05ABEH001699
Published 2003-11-04
Communication , Volume 13, Issue 5, 235-236
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Gataullin R. R. et al. New synthesis of 9-methanesulfonyl-1,2,3,9a-tetrahydro- and 1,2,3,4-tetrahydrocarbazoles from N-methanesulfonyl-2-(cyclohex-1-enyl)aniline // Mendeleev Communications. 2003. Vol. 13. No. 5. pp. 235-236.
GOST all authors (up to 50) Copy
Gataullin R. R., Sotnikov A. M., Abdrakhmanov I. B., Tolstikov G. A. New synthesis of 9-methanesulfonyl-1,2,3,9a-tetrahydro- and 1,2,3,4-tetrahydrocarbazoles from N-methanesulfonyl-2-(cyclohex-1-enyl)aniline // Mendeleev Communications. 2003. Vol. 13. No. 5. pp. 235-236.
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TY - JOUR
DO - 10.1070/MC2003v013n05ABEH001699
UR - https://mendcomm.colab.ws/publications/10.1070/MC2003v013n05ABEH001699
TI - New synthesis of 9-methanesulfonyl-1,2,3,9a-tetrahydro- and 1,2,3,4-tetrahydrocarbazoles from N-methanesulfonyl-2-(cyclohex-1-enyl)aniline
T2 - Mendeleev Communications
AU - Gataullin, Rail Rafkatovich
AU - Sotnikov, Alexander Mikhailovich
AU - Abdrakhmanov, Ildus Barievich
AU - Tolstikov, Genrikh Alexandrovich
PY - 2003
DA - 2003/11/04
PB - Mendeleev Communications
SP - 235-236
IS - 5
VL - 13
ER -
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@article{2003_Gataullin,
author = {Rail Rafkatovich Gataullin and Alexander Mikhailovich Sotnikov and Ildus Barievich Abdrakhmanov and Genrikh Alexandrovich Tolstikov},
title = {New synthesis of 9-methanesulfonyl-1,2,3,9a-tetrahydro- and 1,2,3,4-tetrahydrocarbazoles from N-methanesulfonyl-2-(cyclohex-1-enyl)aniline},
journal = {Mendeleev Communications},
year = {2003},
volume = {13},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2003v013n05ABEH001699},
number = {5},
pages = {235--236},
doi = {10.1070/MC2003v013n05ABEH001699}
}
MLA
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Gataullin, Rail Rafkatovich, et al. “New synthesis of 9-methanesulfonyl-1,2,3,9a-tetrahydro- and 1,2,3,4-tetrahydrocarbazoles from N-methanesulfonyl-2-(cyclohex-1-enyl)aniline.” Mendeleev Communications, vol. 13, no. 5, Nov. 2003, pp. 235-236. https://mendcomm.colab.ws/publications/10.1070/MC2003v013n05ABEH001699.

Abstract

The reaction of N-methanesulfonyl-2-(cyclohex-1-en-1-yl)aniline with Br2 in the presence of NaHCO3 in MeCN results in N-methanesulfonyl-2-(6-bromocyclohex-1-en-1-yl)aniline, which was cyclised to 9-methanesulfonyl-1,2,3,4-tetrahydrocarbazole, and the effect of NH3 leads to 9-methanesulfonyl-1,2,3,9a-tetrahydrocarbazole. The reaction of the latter with molecular bromine in the presence of pyridine results in 1-(9-methanesulfonyl-1,2,3,4-tetrahydro-4-carbazolyl)pyridinium bromide in a good yield.

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