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Stabilized azomethine ylides derived from indeno[1,2-b]quinoxalinones in [3+2] cycloaddition reactions with electrophilic alkenes

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Chemistry of Heterocyclic Compounds Aims and scope

We provide a general and systematic review of all currently published data on the use of stabilized azomethine ylides derived from 11H-indeno[1,2-b]quinoxalin-11-one and 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one in the synthesis of spiropyrrolidines and spiropyrrolizidines. The reaction conditions, as well as the regio- and stereoselectivity of the [3+2] cycloaddition process are discussed. Data on the biological activity of the obtained products are presented. There are 62 literature references.

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References

  1. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A.; Pearson, W. H., Eds.; Wiley: New York, 2002, Vol. 59, p 169.

    Google Scholar 

  2. Tsuge, O.; Kanemasa, S. Adv. Heterocycl. Chem. 1989, 45, 231.

    Article  CAS  Google Scholar 

  3. Arumugam, N.; Suresh Kumar, R.; Almansour, A. I.; Perumal, S. Curr. Org. Chem. 2013, 17, 1929.

    Article  CAS  Google Scholar 

  4. Singh, M. S.; Chowdhury, S.; Koley, S. Tetrahedron 2016, 72, 1603.

    Article  CAS  Google Scholar 

  5. Döndas, H. A.; Retamosa, M. G.; Sansano, J. M. Synthesis 2017, 49, 2819.

    Article  Google Scholar 

  6. Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484.

    Article  CAS  Google Scholar 

  7. Nájera, C.; Sansano, J. M. J. Organomet. Chem. 2014, 771, 78.

    Google Scholar 

  8. Adrio, J.; Carretero, J. C. Chem. Commun. 2014, 50, 12434.

    Article  CAS  Google Scholar 

  9. Nájera, C.; Sansano, J. M. Curr. Top. Med. Chem. 2014, 14, 1271.

    Article  Google Scholar 

  10. Hashimoto, T.; Maruoka, K. Chem. Rev. 2015, 115, 5366.

    Article  CAS  Google Scholar 

  11. Tseng, C.-H.; Chen, Y.-R.; Tzeng, C.-C.; Liu, W.; Chou, C.-K.; Chiu, C.-C.; Chen, Y.-L. Eur. J. Med. Chem. 2016, 108, 258.

    Article  CAS  Google Scholar 

  12. Zhang, C.; Li, S.; Ji, L.; Liu, S.; Li, Z.; Li, S.; Meng, X. Bioorg. Med. Chem. Lett. 2015, 25, 4693.

    Article  CAS  Google Scholar 

  13. Schepetkin, I. A.; Kirpotina, L. N.; Khlebnikov, A. I.; Hanks, T. S.; Kochetkova, I.; Pascual, D. W.; Jutila, M. A.; Quinn, M. T. Mol. Pharmacol. 2012, 81, 832.

    Article  CAS  Google Scholar 

  14. Khan, M. S.; Munawar, M. A.; Ashraf, M.; Alam, U.; Ata, A.; Asiri, A. M.; Kousar, S.; Khan, M. A. Bioorg. Med. Chem. 2014, 22, 1195.

    Article  CAS  Google Scholar 

  15. Zhang, C.; Li, S.; Ji, L.; Liu, S.; Li, Z.; Li, S.; Meng, X. Bioorg. Med. Chem. Lett. 2015, 25, 4693.

    Article  CAS  Google Scholar 

  16. Ruhemann, S. J. Chem. Soc. 1910, 97, 1438.

    Article  CAS  Google Scholar 

  17. Israel, M.; Jones, L. C.; Modest, E. J. J. Heterocycl. Chem. 1972, 9, 255.

    Article  CAS  Google Scholar 

  18. Azizian, J.; Karimi, A. R.; Dastkhan, R.; Mohammadi, A. A.; Mohammadizadeh, M. R. J. Chem. Res. 2004, 347.

  19. Barkov, A. Y.; Zimnitskiy, N. S.; Korotaev, V. Y.; Kutyashev, I. B.; Moshkin, V. S.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2017, 53, 451. [Khim. Geterotsikl. Soedin. 2017, 53, 451.]

  20. Hamzehloueian, M.; Sarrafi, Y.; Aghaei, Z. RSC Adv. 2015, 5, 76368.

    Article  CAS  Google Scholar 

  21. Shahrestani, N.; Salahi, F.; Tavakoli, N.; Jadidi, K.; Hamzehloueian, M.; Notash, B. Tetrahedron: Asymmetry 2015, 26, 1117.

    Article  CAS  Google Scholar 

  22. Filatov, A. S.; Knyazev, N. A.; Ryazantsev, M. N.; Suslonov, V. V.; Larina, A. G.; Molchanov, A. P.; Kostikov. R. R.; Boitsov, V. M.; Stepakov, A. V. Org. Chem. Front. 2018, 5, 595.

    Article  CAS  Google Scholar 

  23. Sobhi, C.; Nacereddine, A. K.; Djerourou, A.; Ríos-Gutiérrez, M; Domingo, L. R. J. Phys. Org. Chem. 2017, 30, 3637.

    Article  Google Scholar 

  24. Kuznetsov, M. L. Russ. Chem. Rev. 2006, 75, 935. [Usp. Khim. 2006, 75, 1045.]

    Article  CAS  Google Scholar 

  25. Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765.

    Article  CAS  Google Scholar 

  26. Shevelev, S. A.; Starosotnikov, A. M. Chem. Heterocycl. Compd. 2013, 49, 92. [Khim. Geterotsikl. Soedin. 2013, 102.]

  27. The Cambridge Crystallographic Data Centre (CCDC) https://www.ccdc.cam.ac.uk

  28. Mani, K. S.; Kaminsky W.; Rajendran, S. P. New J. Chem. 2018, 42, 301.

    Article  Google Scholar 

  29. Barkov, A. Y.; Zimnitskiy, N. S.; Kutyashev, I. B.; Korotaev, V. Y.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2017, 53, 1315. [Khim. Geterotsikl. Soedin. 2017, 53, 1315.]

  30. Moemeni, M.; Arvinnezhad, A.; Samadi, S.; Tajbakhsh, M.; Jadidi, K.; Khavasi, H. R. J. Heterocycl. Chem. 2012, 49, 190.

    Article  CAS  Google Scholar 

  31. Velikorodov, A. V.; Stepkina, N. N. Russ. J. Org. Chem. 2016, 52, 1788. [Zh. Org. Khim. 2016, 52, 1797.]

  32. Mohammadizadeh, M. R.; Firoozi, N. Bull. Korean Chem. Soc. 2009, 30, 1877.

    Article  CAS  Google Scholar 

  33. Nishtala, V. B.; Nanuboli, J. B.; Basavoju, S. Res. Chem. Intermed. 2017, 43, 1365.

    Article  CAS  Google Scholar 

  34. Kathivaran, S.; Raghunathan, R. J. Heterocycl. Chem. 2014, 51, 906.

    Article  Google Scholar 

  35. Babu, A. R. S.; Gavaskar, D.; Raghunathan, R. Tetrahedron Lett. 2012, 53, 6676.

    Article  Google Scholar 

  36. Babu, A. R. S.; Gavaskar, D.; Raghunathan, R. J. Organomet. Chem. 2013, 745-746, 409.

    Article  Google Scholar 

  37. Gavaskar, D.; Babu, A. R. S.; Raghunathan, R.; Dharani, M.; Balasubramanian, S. J. Organomet. Chem. 2014, 768, 128.

    Article  CAS  Google Scholar 

  38. Gavaskar, D.; Babu, A. R. S.; Raghunathan, R.; Dharani, M.; Balasubramanian, S. Steroids 2016, 109, 1.

    Article  CAS  Google Scholar 

  39. Liu, F.-H.; Song, Y.-B.; Zhai, L.-J.; Li, M. J. Heterocycl. Chem. 2015, 52, 322.

    Article  CAS  Google Scholar 

  40. Babu, A. R. S.; Raghunathan, R. Synth. Commun. 2009, 39, 347.

    Article  Google Scholar 

  41. Babu, A. R. S.; Raghunathan, R. Synth. Commun. 2008, 38, 1433.

    Article  CAS  Google Scholar 

  42. Babu, A. R. S.; Raghunathan, R. Tetrahedron Lett. 2006, 47, 9221.

    Article  CAS  Google Scholar 

  43. Gayathri, D.; Aravindan, P. G.; Velmurugan, D.; Ravikumar, K.; Babu, A. R. S. Acta Crystallogr., Sect. E: Crystallogr. Commun. 2005, 61, 3124.

    Article  Google Scholar 

  44. Malathi, K.; Kanchithalaivan, S.; Kumar, R. R.; Almansour, A. I.; Kumar, R. S.; Arumugam, N. Tetrahedron Lett. 2015, 56, 6132.

    Article  CAS  Google Scholar 

  45. Rajesh, S. M.; Bala, B. D.; Perumal, S. Tetrahedron Lett. 2012, 53, 5367.

    Article  Google Scholar 

  46. Rani, M. A.; Kumar, S. V.; Malathi, K.; Muthu, M.; Almansour, A. I.; Kumar, R. S.; Kumar, R. R. ACS Comb. Sci. 2017, 19, 308.

    Article  Google Scholar 

  47. Zimnitskiy, N. S.; Korotaev, V. Yu.; Barkov, A. Yu.; Kutyashev, I. B.; Sosnovskikh, V. Ya. In: From the synthesis of polyethylene to stereodivergence: the developments in chemistry over 100 years [in Russian]. Proceedings of international scientific conference; Perm, 2018, p. 120.

  48. Karsalary, A. A.; Mohammadizadeh, M. R.; Hasaninejad, A. R.; Mohammadi, A. A.; Karimi, A. R. J. Iran. Chem. Soc. 2010, 7, 45.

    Article  CAS  Google Scholar 

  49. Azizian, J.; Karimi, A. R.; Mohammadi, A. A.; Mohammadizadeh, M. R. Synthesis 2004, 2263.

    Article  Google Scholar 

  50. Kathiravan, S.; Raghunathan, R.; Suresh, G.; Siva, G. V. Med. Chem. Res. 2012, 21, 3170.

    Article  CAS  Google Scholar 

  51. Ramesh, E.; Kathiresan, M.; Raghunathan, R. Tetrahedron Lett. 2007, 48, 1835.

    Article  CAS  Google Scholar 

  52. Pattanaik, P.; Nayak, S.; Mishra, D. R.; Panda, P.; Raiguru, B. P.; Mishra, N. P.; Mohapatra, S.; Mallampudi, N. A.; Purohit, C. S. Tetrahedron Lett. 2018, 59, 2688.

    Article  CAS  Google Scholar 

  53. Li, M.; Gong, F.-M.; Wen, L.-R.; Li, Z.-R. Eur. J. Org. Chem. 2011, 3482.

    Article  CAS  Google Scholar 

  54. Velikorodov, A. V.; Stepkina, N. N.; Shustova, E. A.; Ionova, V. A. Russ. J. Org. Chem. 2015, 51, 674. [Zh. Org. Khim. 2015, 51, 693.]

  55. Barkov, A. Y.; Zimnitskiy, N. S.; Kutyashev, I. B.; Korotaev, V. Y.; Sosnovskikh, V. Yа. Chem. Heterocycl. Compd. 2018, 54, 43. [Khim. Geterotsikl. Soedin. 2017, 53, 43.]

  56. Akondi, A. M.; Mekala, S.; Kantam, M. L.; Trivedi, R.; Chowhan, L. R.; Das, A. New J. Chem. 2017, 41, 873.

    Article  CAS  Google Scholar 

  57. Reddy, M. S.; Chowhan, L. R.; Kumar, N. S.; Ramesh, P.; Mukkamala, S. B. Tetrahedron Lett. 2018, 59, 1366.

    Article  CAS  Google Scholar 

  58. Rao, J. N. S.; Raghunathan, R. Tetrahedron Lett. 2015, 56, 2276.

    Article  Google Scholar 

  59. Barkov, A. Y.; Zimnitskiy, N. S.; Korotaev, V. Y.; Kutyashev, I. B.; Moshkin, V. S.; Sosnovskikh, V. Ya. J. Fluorine Chem. 2017, 204, 37.

    Article  CAS  Google Scholar 

  60. Barkov, A. Y.; Zimnitskiy, N. S.; Korotaev, V. Y.; Kutyashev, I. B.; Moshkin, V. S.; Sosnovskikh, V. Ya. Tetrahedron 2016, 72, 6825.

    Article  CAS  Google Scholar 

  61. Lakshmi, N. V.; Thirumurugan, P.; Jayakumar, C.; Perumal, P. T. Synlett 2010, 955.

  62. Rao, J. N. S.; Raghunathan, R. Tetrahedron Lett. 2015, 56, 1539.

    Article  CAS  Google Scholar 

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This work was performed with financial support from the Ministry of Education and Science of the Russian Federation (contract 02.A03.21.0006) and the Russian Foundation for Basic Research (project No. 18-33-00635).

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Authors and Affiliations

  1. Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg, 620000, Russia

    Vladislav Yu. Korotaev, Nikolay S. Zimnitskiy, Alexey Yu. Barkov, Igor B. Kutyashev & Vyacheslav Ya. Sosnovskikh

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  1. Vladislav Yu. Korotaev
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  2. Nikolay S. Zimnitskiy
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  3. Alexey Yu. Barkov
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  4. Igor B. Kutyashev
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  5. Vyacheslav Ya. Sosnovskikh
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Correspondence to Vladislav Yu. Korotaev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(10), 905–922

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Korotaev, V.Y., Zimnitskiy, N.S., Barkov, A.Y. et al. Stabilized azomethine ylides derived from indeno[1,2-b]quinoxalinones in [3+2] cycloaddition reactions with electrophilic alkenes. Chem Heterocycl Comp 54, 905–922 (2018). https://doi.org/10.1007/s10593-018-2369-9

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