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Effect of substituents on isomerization of N-acyl-3-iodo-5-R-1,2,3,3a,4,8b-hexahydrocyclopenta[b]-indoles into 3,4,4a,8c-tetrahydro-2aH-2-oxa-8b-azoniapentaleno[1,6-ab]indenes

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Abstract

Halocyclization of ortho-(2-cyclopenten-1-yl)aniline derivatives provided 3-halosubstituted cyclopenta[b]indoles. Some transformations of the latter were studied.

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References

  1. Gudmundsson, K.S., Sebahar, P.R., D’Aurora Richardson, L., Catalano, J.G., Boggs, S.D., Spaltenstein, A., Sethna, P.B., Brown, K.W., Harvey, R., and Romines, K.R., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 3489. DOI: 10.1016/j.bmcl.2009.05.003.

    Article  CAS  Google Scholar 

  2. Smith, V.A., and Dil’man, A.D., Osnovy sovremennogo ogranicheskogo sinteza (Principles of the Contemporary Organic Synthesis), Moscow: Binom. Laboratiriya Znanii, 2009.

    Google Scholar 

  3. Ishmuratov, G.Yu., Yakovleva, M.P., Ishmuratova, N.M., Tolstikov, A.G., and Tolstikov, G.A., Monoterpenoidy v khimii opticheski aktivnykh feromonov nasekomykh (Monoterpenoids in Chemistry of Optically Active Feromones of Insects), Moscow: Nauka, 2012.

    Google Scholar 

  4. Terent’ev, A.O., Borisov, D.A., Krylov, I.B., and Nikishin, G.I., Synth. Commun., 2007, vol. 37, p. 3151. DOI: 10.1080/00397910701545171.

    Article  Google Scholar 

  5. Zlokazov, M.V., Lozanova, A.V., and Veselovsky, V.V., Mendeleev Commun., 2003, no. 6, p. 242. DOI:10.1070/MC2003v013n 06ABEH001835.

    Google Scholar 

  6. Zlokazov, M.V., Lozanova, A.V., and Veselovsky, V.V., Russ. Chem. Bull. Int. Ed., 2004, p. 547. DOI: 10.1023/B:RUCB.0000035634.33295.0c.

    Google Scholar 

  7. Lozanova, A.V., Ugurchieva, T.M., Zlokazov, M.V., Stepanov, A.V., and Veselovsky, V.V., Mendeleev Commun., 2006, no. 1, p. 15. DOI: 10.1070/MC2006v016n01ABEH002235.

    Google Scholar 

  8. Lozanova, A.V., Ugurchieva, T.M., and Veselovsky, V.V., Russ. Chem. Bull. Int. Ed., 2007, vol. 56, no. 1, p. 130. DOI: 10.1007/s11172-007-0021-4.

    Article  CAS  Google Scholar 

  9. Lozanova, A.V., Stepanov, A.V., and Veselovsky, V.V., Russ. Chem. Bull. Int. Ed., 2010, vol. 59, no. 6, p. 1237. DOI: 10.1007/s11172-010-0227-8.

    Article  CAS  Google Scholar 

  10. Makuc, D., Fabris, J., Časar, Z., and Plavec, J., Molecules, 2013, vol. 18, no. 11, p. 13283. DOI:10.3390/molecules181113283.

    Article  CAS  Google Scholar 

  11. Galkin, E.G., Erastov, A.S., Vyrypaev, E.M., and Furley, I.I., Chem. Heterocycl. Compd., 2013, vol. 49, no. 8, p. 1207. DOI: 10.1007/s10593-013-1364-4.

    Article  CAS  Google Scholar 

  12. Skladchikov, D.A., Buranbaeva, R.S., Fatykhov A.A., Ivanov S.P., and Gataullin R.R., Russ. J. Org. Chem., 2012, vol. 48, no. 12, p. 1550. DOI: 10.1134/S1070428012120093.

    Article  CAS  Google Scholar 

  13. Jong, S.D., Nosal, D.G., and Wardrop, D.J., Tetrahedron, 2012, vol. 68, no. 22, p. 4067. DOI: 10.1016/j.tet.2012.03.036.

    Article  Google Scholar 

  14. Gataullin, R.R., Afon’kin, I.S., Fatykhov, A.A., Spirikhin, L.V., and Abdrakhmanov, I.B., Mendeleev Commun., 2001, no. 5, p. 201. DOI: 10.1070/MC2001v011n05ABEH001490.

    Google Scholar 

  15. Gataullin, R.R., Minnigulov, F.F., Fatykhov, A.A., Spirikhin, L.V., and Abdrakhmanov, I.B., Russ. J. Org. Chem., 2001, vol. 37, no. 9, p. 1289. DOI: 10.1023/A:1013183605455.

    Article  CAS  Google Scholar 

  16. Li, M., Shen, C., J. Org. Chem., 2004, vol. 69, no. 23, p. 7906. DOI: 10.1021/jo0488006.

    Article  Google Scholar 

  17. Gataullin, R.R., Minnigulov, F.F., Kazhanova, T.V., Khakimova, T.V., Fatykhov, A.A., Spirikhin, L.V., and Abdrakhmanov, I.B., Russ. Chem. Bull. Int. Ed, 2001, vol. 50, no. 3, p. 456. DOI: 10.1023/A:1011309223588.

    Article  CAS  Google Scholar 

  18. Gataullin, R.R., Minnigulov, F.F., Khakimova, T.V., Fatykhov, A.A., Spirikhin, L.V., and Abdrakhmanov, I.B., Russ. Chem. Bull. Int. Ed. 2002, vol. 51, no. 7, p. 1329. DOI: 10.1023/A:1020925202293.

    Article  CAS  Google Scholar 

  19. Gataullin, R.R., Kazhanova, T.V., Minnigulov, F.F., Khakimova, T.V., Fatykhov, A.A., Spirikhin, L.V., and Abdrakhmanov, I.B., Russ. J. Org. Chem., 2002, vol. 38, no. 1, p. 31. DOI: 10.1023/A:1015342406252.

    Article  CAS  Google Scholar 

  20. Gataullin, R.R., Minnigulov, F.F., Spirikhin, L.V., and Abdrakhmanov, I.B., Russ. J. Org. Chem., 2004, vol. 40, no. 7, p. 986. DOI: 10.1023/B:RUJO.0000045190.75301.70.

    Article  CAS  Google Scholar 

  21. Gataullin, R.R., Ishbardina, R.R., Sotnikov, A.M., and Abdrakhmanov, I.B., Russ. J. Appl. Chem., 2005, vol. 78, no. 3, p. 438. DOI: 10.1007/s11167-005-0312-1.

    Article  CAS  Google Scholar 

  22. Gataullin, R.R., Ishberdina, R.R., Shitikova, O.V., Minnigulov, F.F., Spirikhin, L.V., and Abdrakhmanov, I.B., Chem. Heterocycl. Compd., 2006, vol. 42, no. 8, p. 1025. DOI: 10.1007/s10593-006-0199-7.

    Article  CAS  Google Scholar 

  23. Gataullin, R.R., Kazhanova, T.V., Minnigulov, F.F., Fatykhov, A.A., Spirikhin, L.V., and Abdrakhmanov, I.B., Russ. Chem. Bull. Int. Ed., 2000, vol. 49, no. 10, p. 1767. DOI: 10.1007/BF02496351.

    Article  CAS  Google Scholar 

  24. Gataullin, R.R., Likhacheva, N.A., Suponitskii, K.Yu., and Abdrakhmanov I.B., Russ. J. Org. Chem., 2007, vol. 43, no. 9, p. 1310. DOI: 10.1134/S1070428007090096.

    Article  CAS  Google Scholar 

  25. Likhacheva, N.A., Abdrakhmanov, I.B., and Gataullin, R.R., Russ. J. Gen. Chem., 2007, vol. 77, no. 4, p. 654. DOI:10.1134/S1070363207040275.

    Article  CAS  Google Scholar 

  26. Likhacheva, N.A., Korlyukov, A.A., and Gataullin, R.R., Russ. J. Org. Chem., 2009, vol. 45, no. 3, p. 394. DOI:10.1134/S1070428009030075.

    Article  CAS  Google Scholar 

  27. Skladchikov, D.A., Suponitskii, K.Yu., Abdrakhmanov, I.B., and Gataullin, R.R., Russ. J. Org. Chem., 2012, vol. 48, no. 7, p. 957. DOI: 10.1134/S1070428012070123.

    Article  CAS  Google Scholar 

  28. Skladchikov, D.A., Fatykhov, A.A., and Gataullin, R.R., Russ. J. Org. Chem., 2014, vol. 50, no. 1, p. 48. DOI:10.1134/S1070428014010096.

    Article  CAS  Google Scholar 

  29. Gataullin, R.R., Afon’kin, I.S., Fatykhov, A.A., Spirikhin, L.V., and Abdrakhmanov, I.B., Russ. Chem. Bull. Int. Ed., 2000, vol. 49, no. 1, p. 122. DOI:10.1007/BF02499076.

    Article  CAS  Google Scholar 

  30. HyperChem 8.0. www.hyper.com .

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Correspondence to R. R. Gataullin.

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Original Russian Text © M.A. Bagamanova, R.R. Gataullin, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 3, pp. 447–453.

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Bagamanova, M.A., Gataullin, R.R. Effect of substituents on isomerization of N-acyl-3-iodo-5-R-1,2,3,3a,4,8b-hexahydrocyclopenta[b]-indoles into 3,4,4a,8c-tetrahydro-2aH-2-oxa-8b-azoniapentaleno[1,6-ab]indenes. Russ J Gen Chem 85, 611–617 (2015). https://doi.org/10.1134/S1070363215030147

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