Abstract
Intramolecular cyclization ofo-alkenylanilines was studied. Heating ofo-(cyclopent-2-en-1-yl) arylammonium chlorides at 200–220 °C yields cyclopenta[b]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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
B. Robinson,Chem. Rev., 1969,69, 227.
I. B. Abdrakhmanov, A. G. Mustafin, V. M. Sharafutdinov, A. S. Taichinova, and G. A. Tolstikov,Izv. Akad. Nauk SSSR, Ser. Khim., 1985, 839 [Bull. Acad. Sci. USSR, Div. Chem. Sic., 1985,34, 760 (Engl. Transl.)].
A. G. Mustafin, R. R. Gatallin, I. B. Abdrakhmanov, L. M. Khalilov, and G. A. Tolstikov,Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 2811 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990,39, 2551 (Engl. Transl.)].
O. L. Chapman and G. L. Eian,J. Am. Chem. Soc., 1968,90, 5329.
A. B. Shapiro, A. A. Medzhidov, and E. G. Rosantsev,Zh. Org. Khim., 1966,2, 1873 [J. Org. Chem. (USSR), 1966,2 (Engl. Transl.)].
A. G. Mustafin, I. N. Khalilov, I. B. Abdrakhmanov, and G. A. Tolstikov,Khim. Prir. Soedin., 1989,6, 816 [Chem. Nat. Compd., 1989,6 (Engl. Transl.)].
A. G. Mustafin, I. N. Khalilov, V. M. Sharafutdinov, D. I. D'yachenko, I. B. Abdrakhmanov, and G. A. Tolstikov,Izv. Akad. Nauk, Ser. Khim., 1997, 630 [Russ. Chem. Bull., 1997,46, 608 (Engl. Transl.)].
I. B. Abdrakhmanov, V. M. Sharafutdinov, and G. A. Tolstikov,Izv. Akad. Nauk SSSR, Ser. Khim., 1982, 2160 [Bull. Acad. Sci. USSR, Div. Chem. Sic., 1982,31 (Engl. Transl.)].
I. B. Abdrakhmanov, V. M. Sharafutdinov, G. A. Tolstikov, U. M. Dzhemilev, E. V. Tal'finskii, and I. A. Sagitdinov,Zh. Prikl. Khim., 1982, 2121.
L. A. Kazitsyna and N. B. Kupletskaya, inPrimenenie UF-, IK-, YaMR- i mass-spektroskopii v organicheskoi khimii [Application of UV, IR, NMR, and Mass Spectroscopy in Organic Chemistry], Izd. MGU, Moscow, 1979, 77 (in Russian).
A. J. Gordon and R. A. Ford,The Chemist's Companion. A Handbook of Practical Data, Techniques, and References, Wiley Interscience, New York-London, 1972.
B. I. Ionin, B. A. Ershov, and A. I. Kol'tsov,YaMR-spektroskopiya v organischeskoi khimii [NMR Spectroscopy in Organic Chemistry], Khimiya, Leningrad, 1983, 142 pp. (in russian).
J. E. Hyre and A. R. Bader,J. Am. Chem. Soc., 1958,80, 437.
A. R. Bader, R. J. Bridgwater, and P. R. Freeman,J. Am. Chem. Soc., 1961,83, 3319.
M. Schmid, H.-J. Hansen, and H. Schmid,Helv. Chim. Acta, 1971,54, 937.
L. M. Jackman and S. Sternhell, inApplication of Nuclear Magnetic Resonance in Orgnaic Chemistry, Pergamon Press, Oxford, 1969, 236.
J. B. Stothers and C. T. Tan,Can. J. Chem., 1974,52, 303.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 975–978, May, 1999.
Rights and permissions
About this article
Cite this article
Gataullin, R.R., Kazhanova, T.V., Il'yasova, L.T. et al. Synthesis of indolines and tetrahydroquinolines fromortho-(alk-2-enyl)anilines. Russ Chem Bull 48, 967–970 (1999). https://doi.org/10.1007/BF02494646
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02494646