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Synthesis of 1-iodo-1,2,3,4,4a,9a-hexahydrocarbazoles and their isomerization into 3-iodo-2,4-propano-1,2,3,4-tetrahydroquinolines

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Abstract

The reactions of 2-(cyclohex-2-enyl)-4,5-difluoroaniline or N-methyl-2-(cyclohex-2-enyl)aniline with I2 in CCl4 in the presence of NaHCO3 give 1-iodo-1,2,3,4,4a,9a-hexahydrocarbazoles, which isomerize in MeCN into the corresponding 3-iodo-2,4-propano-1,2,3,4-tetrahydroquinolines in quantitative yields.

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Authors and Affiliations

  1. Ufa Research Center of the Russian Academy of Sciences, Institute of Organic Chemistry, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    R. R. Gataullin, T. V. Khakimova, A. A. Fatykhov, L. V. Spirikhin & I. B. Abdrakhmanov

  2. Bashkir State Agricultural University, 34 ul. 50-letya Oktyabrya, 450003, Ufa, Russian Federation

    F. F. Minnigulov

Authors
  1. R. R. Gataullin
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  2. F. F. Minnigulov
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  3. T. V. Khakimova
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  4. A. A. Fatykhov
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  5. L. V. Spirikhin
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  6. I. B. Abdrakhmanov
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Gataullin, R.R., Minnigulov, F.F., Khakimova, T.V. et al. Synthesis of 1-iodo-1,2,3,4,4a,9a-hexahydrocarbazoles and their isomerization into 3-iodo-2,4-propano-1,2,3,4-tetrahydroquinolines. Russian Chemical Bulletin 51, 1329–1331 (2002). https://doi.org/10.1023/A:1020925202293

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