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Chemo- and regioselective oxidation of substituted 2,3,4,9-tetrahydro-1H-carbazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Chemo- and regioselective oxidation of substituted 2,3,4,9-tetrahydro-1H-carbazoles was used to obtain 2,3,4,9-tetrahydro-1H-carbazol-1-ones or 3,4,5,6-tetrahydro-1H-1-benzazonine-2,7-diones depending on the nature of the selected oxidant. In the case of benzo-fused tetrahydrocarbazoles, the main direction of the process was complete aromatization of the polycyclic system. Besides the influence of the substrate type, we also explored the role of various oxidants, solvents, and the concentration of reactants in this oxidation process.

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References

  1. Mahboobi, S.; Kuhr, S.; Meindl, W. Arch. Pharm. 1994, 327, 611.

    Article  CAS  Google Scholar 

  2. Su, L.; Li, J.; Zhou, Z.; Huang, D.; Zhang, Y.; Pei, H.; Guo, W.; Wu, H.; Wang, X.; Liu, M.; Yang, C.-G.; Chen, Y. Eur. J. Med. Chem. 2019, 162, 203.

    Article  CAS  Google Scholar 

  3. Bublitz, L.; Kjellerup, L.; Cohrt, K. O'H.; Gordon, S.; Mortensen, A. L.; Clausen, J. D.; Pallin, T. D.; Hansen, J. B.; Fuglsang, A. T.; Dalby-Brown, W.; Winther, A.-M. L. PLoS One 2018, 13, e0188620.

  4. Kulkarni, M. R.; Mane, M. S.; Ghosh, U.; Sharma, R.; Lad, N. P.; Srivastava, A.; Kulkarni-Almeida, A.; Kharkar, P. S.; Khedkar, V. M.; Pandit, S. S. Eur. J. Med. Chem. 2017, 134, 366.

    Article  CAS  Google Scholar 

  5. Chen, J.; Lou, J.; Liu, T.; Wu, R.; Dong, X.; He, Q.; Yang, B.; Hu, Y. Arch. Pharm. 2009, 342, 165.

    Article  CAS  Google Scholar 

  6. Zhang, J.-Q.; Li, S.-M.; Ma, X.; Zhong, G.; Chen, R.; Li, X.-S.; Zhu, G.-F.; Zhou, B.; Guo, B.; Wu H.-S.; Tang, L. Eur. J. Med. Chem. 2018, 150, 102.

    Article  CAS  Google Scholar 

  7. Joseph, D.; Martarello, L.; Kirsch, G. J. Chem. Res. (S) 1995, 9, 350.

    Google Scholar 

  8. Thangavel, S. K.; Mohamed Subarkhan, M. K.; Rengan, R.; Wang, H.; Malecki, J. Dalton Trans. 2020, 49, 11385.

    Article  Google Scholar 

  9. Chen, W.; Zhao, S.; Wang, Y.; Zhou, Y.; Ye, W.; Li, X.; Peng, W. CN Patent CN110950873(A).

  10. Kotha, S.; Aswar, V. R.; Singhal, G. Tetrahedron 2017, 73, 6436.

    Article  CAS  Google Scholar 

  11. Yoshida, K.; Goto, J.; Ban, Y. Chem. Pharm. Bull. 1987, 35, 4700.

    Article  CAS  Google Scholar 

  12. Llopis, N.; Gibsert, P.; Baeza, A. Adv. Synth. Catal. 2021, 363, 3245.

    Article  CAS  Google Scholar 

  13. Majetich, G.; Hull, K.; Casares, A. M.; Khetani, V. J. Org. Chem. 1991, 56, 3958.

    Article  CAS  Google Scholar 

  14. Gracia, J.; Casamitjana, N.; Bonjoch, J.; Bosch, J. J. Org. Chem. 1994, 59, 3939.

    Article  CAS  Google Scholar 

  15. Lavoie, E. J.; Parhi, A.; Sagong, H. Y. WO Patent 2019005841A1.

  16. Sakai, S.-I.; Kubo, A.; Katsuura, K.; Mochinaga, K.; Ezak, M. Chem. Pharm. Bull. 1972, 20, 76.

    Article  CAS  Google Scholar 

  17. Tang, F.; Banwell, M. G.; Willis, A. C. J. Org. Chem. 2016, 81, 2950.

    Article  CAS  Google Scholar 

  18. Crosby, U. R.; Corson, B. B. Org. Synth. 1950, 30, 90.

    Article  Google Scholar 

  19. Marçala, L. L.; Garden, S. J. J. Braz. Chem. Soc. 2019, 30, 19.

    Google Scholar 

  20. Owellen, R. J. J. Org. Chem. 1974, 39, 69.

    Article  CAS  Google Scholar 

  21. Młochowski, J.; Wójtowicz-Młochowska, H. Molecules 2015, 20, 10205.

    Article  Google Scholar 

  22. Singleton, D. A.; Hang, C. J. Org. Chem. 2000, 65, 7554.

    Article  CAS  Google Scholar 

  23. He, X.; Zhuo, X.-T.; Gao, Y.; Bai, R.; Ye, X.-Y.; Xie, T. R. Soc. Open Sci. 2020, 7, 200038.

    Article  CAS  Google Scholar 

  24. Allen, F. L.; Suschitzky, H. J. Chem. Soc. 1953, 3845.

  25. Lieb, H.; Schöniger, W. Anleitung zur Darstellung organischer Präparate mit kleinen Substanzmengen; Springer-Verlag: Vienna, 1961, S. 111.

    Book  Google Scholar 

  26. Krüll, J.; Hubert, A.; Nebel, N.; Prante, O.; Heinrich, M. R. Chem.–Eur. J. 2017, 23, 16174.

    Article  Google Scholar 

  27. Collar, W. M.; Plant, S. G. J. Chem. Soc. 1926, 129, 808.

    Article  Google Scholar 

  28. Angnes, R. A.; Potnis, C.; Liang, S.; Correia, C. R. D.; Hammond, G. B. J. Org. Chem. 2020, 85, 4153.

    Article  CAS  Google Scholar 

  29. Stadlbauer, W.; Dang, H. V.; Berger, B. S. J. Heterocycl. Chem. 2010, 47, 807.

    Article  CAS  Google Scholar 

  30. Ghiyasabadi, Z.; Bahadorikhalili, S.; Saeedi, M.; Karimi- Niyazagheh, M.; Mirfazli, S. S. J. Heterocycl. Chem. 2019, 57, 606.

  31. Mari, G.; Crescentini, L. D.; Favi, G.; Santeusanio, S.; Mantellini, F. Eur. J. Org. Chem. 2020, 33, 5411.

    Article  Google Scholar 

  32. Willis, M. C.; Brace, G. N.; Holmes, I. P. Angew. Chem., Int. Ed. 2005, 44, 403.

    Article  CAS  Google Scholar 

  33. Huisgen, R. Liebigs Ann. 1948, 559, 101.

    Article  CAS  Google Scholar 

  34. Bellezza, D.; Zaragozá, R. J.; José Aurell, M.; Ballesteros, R.; Ballesteros-Garrido, R. Org. Biomol. Chem. 2021, 19, 677.

    Article  CAS  Google Scholar 

  35. Campaigne, E.; Lake, R. D. J. Org. Chem. 1959, 24, 478.

    Article  CAS  Google Scholar 

  36. Liu. G.; Lancefield, C.; Lorion, M.; Slawin, A.; Westwood, N. Synthesis 2014, 2808.

  37. Desikachari, S.; Prasad, K. J. R. Heterocycles 1986, 24, 711.

    Article  Google Scholar 

  38. Shi, H.; Guo, T.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Tetrahedron 2014, 70, 2753

    Article  CAS  Google Scholar 

  39. Edkins, R. M.; Hayden, E.; Steed, J. W.; Fucke, K. Chem. Commun. 2015, 51, 5314.

    Article  CAS  Google Scholar 

  40. Qu, Z.; Chen, X.; Zhong, S.; Deng, G.-J.; Huang, H. Org. Lett. 2021, 23, 5349.

    Article  CAS  Google Scholar 

  41. Shagalov, L. B.; Eraksina, V. N.; Turchin, K. N.; Suvorov, N. N. Chem. Heterocycl. Compd. 1970, 6, 878.

    Article  Google Scholar 

  42. Guerra, W. D.; Rossi, R. A.; Pierini, A. B.; Barolo, S. M. J. Org. Chem. 2015, 80, 928.

    Article  CAS  Google Scholar 

  43. Rivett, D. E.; Wilshire, J. F. K. Aust. J. Chem. 1971, 24, 2717.

    Article  CAS  Google Scholar 

  44. Mateo, C. A.; Urrutia, A.; Rodriguez, J. G.; Fonseca, I.; Cano, F. H. J. Org. Chem. 1996, 61, 810.

    Article  CAS  Google Scholar 

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Correspondence to Alexander I. Savelyev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(8/9), 403–411

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Mikhalyonok, S.G., Savelyev, A.I., Kuz’menok, N.M. et al. Chemo- and regioselective oxidation of substituted 2,3,4,9-tetrahydro-1H-carbazoles. Chem Heterocycl Comp 58, 403–411 (2022). https://doi.org/10.1007/s10593-022-03106-6

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