Abstract
When reacting with I2, 2-(cyclopent-2-enyl)anilines undergo cyclization into 3-iodo-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indoles in high yields. The minor reaction products were 3,5- or 3,7-diiodoindolines. Ammonolysis of 3-iodo-5-methyl-1,2,3,3a,4,8b-hexahydro-cyclopenta[b]indole or itsN-chloroacetyl derivative results in 3-amino-5-methyl-1,2,3,3a,48b-hexahydro- and 5-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles.
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References
A. B. Smith, J. Kingery-Wood, T. L. Leenay, E. G. Nolen, and T. Sunazuka,J. Am. Chem. Soc., 1992,114, 1438.
S. Jyh-Horng, C. Yua-Kuang, and V. H. Yen-Long,Tetrahedron Lett., 1991,32, No. 8, 1045;Ref. Zh. Khim. (Abstract Journal Chemistry), 1992, 16E124.
W. H. Perkin and J. S. G. Plant,J. Chem. Soc., 1923, 3242 [Chem. Abstrs., 1924,18, 6872].
R. R. Gataullin, T. V. Kazhanova, L. T. Il'yasova, A. A. Fatykhov, L. V. Spirikhin, and I. B. Abdrakhmanov,Izv. Akad. Nauk, Ser. Khim., 1999, 975 [Russ. Chem. Bull., 1999.48, 967 (Engl. Transt.)].
I. B. Abdrakhmanov, A. G. Mustafin, I. N. Khalilov, and G. A. Tolstikov,Izv. Akad. Nauk SSSR, Ser. Khim., 1983, 2172 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1983,32, 1965 (Engl. Transl.)].
O. L. Chapman and G. L. Eian,J. Am. Chem. Soc., 1968.90, 5329.
M. Watanabe, H. Okada, T. Teshima, M. Noguchi, and A. Kakehi,Tetrahedron, 1996,52, No. 8, 2827.
K. D. Raner and A. D. Ward,Aust. J. Chem., 1991,44, 1749.
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.)].
J. E. Baldwin,J. Chem. Soc., Chem. Commun., 1976, 734.
Weygand-Hilgetag,Organisch-chemische Experimentierkunst, herausgegeben von P. H. C. Hilgetag, 3.Neubearbeitete Auflage, Johann Ambrosius Barth Verlag, Leipzig, 1964.
C. S. Dexter, I. Elliot, and R. F. W. Jackson, Book of Abstracts,16th Int. Symp. on Synthesis in Organic Chemistry, 19–22 July, Cambridge, 1999, p. 11.
R. R. Gataullin, I. S. Afon'kin, A. A. Fatykhov, and I. B. Abdrakhmanov,Izv. Akad. Nauk, Ser. Khim., 2000, 118 [Russ. Chem. Bull., Int. Ed., 2000,49, 122 (Engl. Transl.)].
B. I. Ionin, B. A. Ershov, and A. I. Kol'tsov,Ya MR-spektro-skopiya v organicheskoi khimii [NMR Spectroscopy in Organic Chemistry]. Khimiya, Leningrad, 1983, 142 pp. (in Russian).
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Published inIzvestiya Akademii Nauk. Seriya Khimischeskaya, No. 10, pp. 1789–1793, October, 2000.
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Gataullin, R.R., Kazhanova, T.V., Minnigulov, F.F. et al. Synthesis of 3-substituted cyclopenta[b]indoles. Russ Chem Bull 49, 1767–1770 (2000). https://doi.org/10.1007/BF02496351
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DOI: https://doi.org/10.1007/BF02496351