Synthesis of indolines and tetrahydroquinolines fromortho-(alk-2-enyl)anilines |
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| Authors: | R R Gataullin T V Kazhanova L T Il'yasova A A Fatykhov L V Spirikhin I B Abdrakhmanov |
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| Institution: | (1) Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054 Ufa, Russian Federation;(2) Bashkir State Agricultural University, 34 ul. 50-letiya Oktyabrya, 450003 Ufa, Russian Federation |
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| Abstract: | Intramolecular cyclization ofo-alkenylanilines was studied. Heating ofo-(cyclopent-2-en-1-yl) arylammonium chlorides at 200–220 °C yields cyclopentab]indolines as the main reaction products. Cyclization of 4-methyl-2-(pent-3-en-2-yl)aniline under the same conditions gave
a mixture of indolines and tetrahydroquinolines. An alk-1-enylarylamine containing a vinylic double bond does not form cyclization
products on the nitrogen atom.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 975–978, May, 1999. |
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| Keywords: | 2-methyl-6-(cyclopent-2-en-1-yl)aniline 2 4-dimethyl-6-(cyclopent-2-en-1-yl)aniline intramolecular cyclization cyclopenta[b]indolines 2 4 6-trimethyl-1 2 3 4-tetrahydroquinolines 3 5-dimethyl-2-ethylindoline 1 2 3 3a 4 8b-hexahydrocyclopenta[b]indoles |
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