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Multicomponent synthesis of 1,5,6,7-tetrahydro-4H-indol-4-one derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

The data on multicomponent methods of tetrahydro-4H-indol-4-one synthesis published over the past ten years are summarized in this review. Three main synthetic approaches in the construction of such molecules are considered. Among them are: condensation of cyclohexane-1,3-diones with α-halogenoketones and primary amines, three-component reaction of cyclic enaminoketones, arylglyoxals, and methylene active compounds, and condensation of cyclic enaminoketones and arylglyoxals in the presence of nucleophilic reagents (often solvents). The latter domino reaction runs under microwave irradiation and leads to the functionalization of position 7 of the indole ring system. The material is systematized according to the structure of the starting compounds.

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References

  1. Sharma, V.; Kumar, P.; Pathak, D. J. Heterocycl. Chem. 2010, 47, 491.

    Article  CAS  Google Scholar 

  2. Horsten, T.; Dehaen, W. Molecules 2021, 26, 4596.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Vojacek, S.; Schulig, L.; Wössner, N.; Geist, N.; Langel, W.; Jung, M.; Schade, D.; Link, A. ChemMedChem 2019, 14, 853.

    Article  CAS  PubMed  Google Scholar 

  4. Kamel, A.; Obach, R. S.; Tseng, E.; Sawant, A. Xenobiotica 2010, 40, 400.

    Article  CAS  PubMed  Google Scholar 

  5. Sun, L.; Tran, N.; Liang, C.; Hubbard, S.; Tang, F.; Lipson, K.; Schreck, R.; Zhou, Y.; McMahon, G.; Tang, G. J. Med. Chem. 2000, 43, 2655.

    Article  CAS  PubMed  Google Scholar 

  6. Mohammadi Ziarani, G.; Moradi, R.; Ahmadi, T.; Lashgari, N. RSC Adv. 2018, 8, 12069.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Stetter, H.; Siehnhold, E. Chem. Ber. 1955, 88, 271.

    Article  CAS  Google Scholar 

  8. Gonzalez-Chavez, R.; Martinez, R.; Torre-Bouscoulet, M. E.; Gallo, M.; Gonzalez-Chavez, M. M. Chem. Pharm. Bull. 2014, 62, 16.

    Article  CAS  Google Scholar 

  9. Dominguez-Villa, F. X.; Duran-Iturbide, N. A.; Avila-Zarraga, J. G. Bioorg. Chem. 2021, 106, 104497.

    Article  CAS  PubMed  Google Scholar 

  10. Sulur, M.; Sharma, P.; Ramakrishnan, R.; Naidu, R.; Merifield, E.; Gill, D. M.; Clarke, A. M.; Thomson, C.; Butters, M.; Bachu, S.; Benison, C. H.; Dokka, N.; Fong, E. R.; Hose, D. R. J.; Howell, G. P.; Mobberley, S. E.; Morton, S. C.; Mullen, A. K.; Rapai, J.; Tejas, B. Org. Process Res. Dev. 2012, 16, 1746.

    Article  CAS  Google Scholar 

  11. Li, R.-K.; Wang, Q.-L.; Liu, Y.; Li, D.-W.; Huang, N.-Y.; Liu, M.-G. Chin. Chem. Lett. 2015, 27, 345.

    Article  Google Scholar 

  12. Abdel-Mohsen, S.; El-Emary, T. ARKIVOC 2016, (iv), 184.

  13. Dinne, N. K. R.; Mekala, R.; Reddy, S. P.; Siva, S. G. Y.; Bannoath, Ch. K. Synth. Commun. 2018, 48, 1649.

    Article  CAS  Google Scholar 

  14. Dhananjaya, G.; Dhanunjaya Rao, A. V.; Hossain, K. A.; Venkateswara Rao, A.; Pal, M. Tetrahedron Lett. 2020, 61, 151972.

    Article  CAS  Google Scholar 

  15. Lambat, T. L.; Abdala, A. A.; Mahmood, S.; Ledade, P. V.; Chaudhary, R. G.; Banerjee, S. RSC Adv. 2019, 9, 39735.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Ansari, K.; Nazeef, M.; Ali, S.; Waseem, M. A.; Shah, W. A.; Ansari, S.; Siddiqui, I. R.; Singh, J. J. Heterocycl. Chem. 2021, 58, 622.

    Article  CAS  Google Scholar 

  17. Reddy, G. N.; Likhar, P. R. Res. Chem. Intermed. 2016, 42, 6873.

    Article  CAS  Google Scholar 

  18. Modugu, N. R.; Pittala, R. K. Cogent Chem. 2017, 3, 1318693.

    Article  Google Scholar 

  19. Wang, H.-Y.; Shi, D.-Q. ACS Comb. Sci. 2013, 15, 261.

    Article  CAS  PubMed  Google Scholar 

  20. Kolos, N. N.; Marchenko, E. I.; Chechina, N. V.; Buravov, A. V.; Omelchenko, I. V. Chem. Heterocycl. Compd. 2021, 57, 1181.

    Article  CAS  Google Scholar 

  21. Chechina, N. V; Kolos, N. N.; Omelchenko, I. V. Chem. Heterocycl. Compd. 2019, 55, 1190.

    Article  CAS  Google Scholar 

  22. Dommaraju, Y.; Borthakur, S.; Rajesh, N.; Prajapati, D. RSC Adv. 2015, 5, 24327.

    Article  CAS  Google Scholar 

  23. Maity, S.; Pathak, S.; Pramanik, A. Eur. J. Org. Chem. 2014, 4651.

  24. Bayat, M.; Nasri, S.; Notash, B. Tetrahedron 2017, 73, 1522.

    Article  CAS  Google Scholar 

  25. Andin, A. A. Chem. Heterocycl. Compd. 2021, 57, 26.

    Article  CAS  Google Scholar 

  26. Amaye, I. J.; Haywood, R. D.; Mandzo, E. M.; Wirick, J. J.; Jackson-Ayotunde, P. L. Tetrahedron 2021, 83, 131984.

    Article  CAS  Google Scholar 

  27. Wang, S.-S.; Zhu, Q.-W.; Liu, S. Res. Chem. Intermed. 2015, 41, 2879.

    Article  CAS  Google Scholar 

  28. Javahershenas, R.; Khalafy, J. Heterocycl. Commun. 2018, 24, 37.

    Article  CAS  Google Scholar 

  29. Javahershenas, R.; Khalafy, J. J. Mex. Chem. Soc. 2018, 62, 1.

    CAS  Google Scholar 

  30. Wang, L.; Shi, L.-X.; Liu, L.; Li, Z.-X.; Xu, T.; Hao, W.-J.; Li, G.; Tu, S.-J.; Jiang, B. J. Org. Chem. 2017, 82, 3605.

    Article  CAS  PubMed  Google Scholar 

  31. Shi, Q.-Q.; Fu, L.-P.; Shi, Y.; Ding, H.-Q.; Luo, J.-H.; Jiang, B.; Tu, S.-J. Tetrahedron Lett. 2013, 54, 3176.

    Article  CAS  Google Scholar 

  32. Li, Y.; Li, Q.-Y.; Xu, H.-W.; Fan, W.; Jiang, B.; Wang, S.-L.; Tu, S.-J. Tetrahedron 2013, 69, 2941.

    Article  CAS  Google Scholar 

  33. Fu, L.-P.; Shi, Q.-Q.; Shi, Y.; Jiang, B.; Tu, S.-J. ACS Comb. Sci. 2013, 15, 135.

    Article  PubMed  Google Scholar 

  34. Maity, S.; Pathak, S.; Pramanik, A. Eur. J. Org. Chem. 2013, 2479.

  35. Tu, X.-C.; Fan, W.; Jiang, B.; Wang, S.-L.; Tu, S.-J. Tetrahedron 2013, 69, 6100.

    Article  CAS  Google Scholar 

  36. Pramanik, S.; Maity, S.; Ghosh, P.; Mukhopadhyay, C. Tetrahedron Lett. 2019, 60, 435.

    Article  CAS  Google Scholar 

  37. Jiang, B.; Li, Q-Y.; Tu, M.-S.; Wang, S.-L.; Tu, S.-J.; Li, G. J. Org. Chem. 2012, 77, 7497.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  38. Jiang, B.; Li, Q.-Y.; Zhang, H.; Tu, S.-J.; Pindi, S.; Li, G. Org. Lett. 2012, 14, 700.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  39. Shinde, V. V.; Lee, S. M.; Oh, J. S.; Lim, K. T.; Jeong, Y. T. Synth. Commun. 2016, 46, 1145.

    Article  CAS  Google Scholar 

  40. Li, Ch.; Liang, X.; Zhang, F.; Qi, Ch. Catal. Commun. 2015, 62, 6.

    Article  CAS  Google Scholar 

  41. Fang, J.; Yan, C.-G. J. Heterocycl. Chem. 2016, 53, 800.

    Article  CAS  Google Scholar 

  42. Reddy, M. N.; Kumar, P. P. Tetrahedron Lett. 2017, 58, 4790.

    Article  Google Scholar 

  43. Rahimi, F.; Bayat, M.; Hosseini, F. S.; Kozakiewicz, A. Heliyon 2019, 5, e01456.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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Authors and Affiliations

  1. Kharkiv Karazin National University, 4 Svobody Sq., Kharkiv, 61022, Ukraine

    Kateryna I. Marchenko & Nadiia N. Kolos

Authors
  1. Kateryna I. Marchenko
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  2. Nadiia N. Kolos
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Correspondence to Nadiia N. Kolos.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(11/12), 717–722

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Marchenko, K.I., Kolos, N.N. Multicomponent synthesis of 1,5,6,7-tetrahydro-4H-indol-4-one derivatives. Chem Heterocycl Comp 59, 717–722 (2023). https://doi.org/10.1007/s10593-024-03260-z

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