R. R. Gataullin, A. M. Sotnikov, I. B. Abdrakhmanov, G. A. Tolstikov, “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 Commun., 13:5 (2003), 235

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.

This publication is cited in the following 10 articles:

Rail R. Gataullin, “Halolactonization of N-Acyl-N-(2-cyclohex-1-en-1-yl-6-methylphenyl)glycines: Towards Production of 4,1-Benzoxazoheterocycles”, Synthesis, 55:13 (2023), 2053
R. R. Gataullin, “Synthesis of Atropisomeric Benzoxazocines Based on Etherification Products of N-[2-(Cycloalk-1-en-1-yl)phenyl]sulfonamides with Ethylene Chlorohydrin”, Russ J Org Chem, 59:12 (2023), 2157
Galal H. Elgemeie, Rasha A. Azzam, Wafaa A. Zaghary, Ashraf A. Aly, Nadia H. Metwally, Mona O. Sarhan, Elshimaa M. Abdelhafez, Rasha E. Elsayed, N-Sulfonated-N-Heterocycles, 2022, 345
R. R. Gataullin, “Formation of Benzo[e]cycloalk[g][1,4]oxazocinones by Reaction of N-Mesyl- or N-Tosyl-N-2-[(1-cycloalken-1-yl)phenyl]glycines with Molecular Bromine”, Russ J Gen Chem, 91:8 (2021), 1484
R. N. Khusnitdinov, R. M. Sultanov, R. R. Gataullin, “Functiaonalization of 2-(1-Cyclohexen-1-yl)aniline Derivatives”, Russ J Gen Chem, 89:4 (2019), 653
N. A. Likhacheva, E. K. Aminova, “Progress in the Synthesis of Partially Hydrogenated Carbazoles”, BCJ, 25:3 (2018), 67
R. R. Gataullin, “Synthesis of compounds containing a cycloalka[b]indole fragment”, Russ J Org Chem, 45:3 (2009), 321
R. R. Gataullin, R. R. Ishberdina, A. M. Sotnikov, I. B. Abdrakhmanov, “Synthesis of 6-Methyl-4-(1-methyl-2-buten-1-yl)-2-(2-cyclohexen-1-yl)- and 6-Methyl-4-(1-methyl-2-buten-1-yl)-2-(1-cyclohexen-1-yl)anilines”, Russ J Appl Chem, 78:3 (2005), 438
R. R. Gataullin, A. M. Sotnikov, L. V. Spirikhin, I. B. Abdrakhmanov, “Reactions of N-and C-Alkenylanilines: VII. Synthesis of Indole Heterocycles from Products of Reaction between N-Mesyl-2-(1-alken-1-yl)anilines and Halogens”, Russ J Org Chem, 41:5 (2005), 715
Rail R. Gataullin, Alexander M. Sotnikov, Ildus B. Abdrakhmanov, Genrikh A. Tolstikov, “New Synthesis of 9‐Methanesulfonyl‐1,2,3,9a‐tetrahydro‐ and 1,2,3,4‐tetrahydrocarbazoles from N‐Methanesulfonyl‐2‐(cyclohex‐1‐enyl)aniline.”, ChemInform, 35:9 (2004)