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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| Authors: | R R Gataullin F F Minnigulov T V Khakimova A A Fatykhov L V Spirikhin I B Abdrakhmanov |
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| Institution: | (1) Ufa Research Center of the Russian Academy of Sciences, Institute of Organic Chemistry, 71 prosp. Oktyabrya, 450054 Ufa, Russian Federation;(2) Bashkir State Agricultural University, 34 ul. 50-letya Oktyabrya, 450003 Ufa, Russian Federation |
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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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| Keywords: | cyclohexenylanilines iodocyclization hexahydrocarbazoles 3-iodo-2 4-propano-1 2 3 4-tetrahydroquinolines |
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