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Mechanochemical synthesis of halogenated heterocyclic compounds

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Chemistry of Heterocyclic Compounds Aims and scope

Data on the mechanochemical synthesis of halogenated heterocyclic compounds was summarized and analyzed. Special consideration was paid to the reaction mechanism and the problem of selectivity.

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References

  1. Benedetto Tiz, D.; Bagnoli, L.; Rosati, O.; Marini, F.; Sancineto, L.; Santi, C. Molecules 2022, 27, 1643.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Mei, H.; Han, J.; White, S.; Graham, D. J.; Izawa, K.; Sato, T.; Fustero, S.; Meanwell, N. A.; Soloshonok, V. A. Chem.–Eur. J. 2020, 26, 11349.

  3. Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Aceña, J. L.; Soloshonok, V. F.; Izawa, K.; Liu, H. Chem. Rev. 2016, 116, 422.

    Article  CAS  PubMed  Google Scholar 

  4. Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.

    Article  CAS  PubMed  Google Scholar 

  5. Zaikin, P. A.; Borodkin, G. I. In Late-Stage Fluorination of Bioactive Molecules and Biologically-Relevant Substrates; Postigo, A., Ed.; Elsevier: Amsterdam, 2019, p. 105.

  6. Lowe, P. T.; O'Hagan, D. Chem. Soc. Rev. 2023, 52, 248.

    Article  CAS  PubMed  Google Scholar 

  7. Mykhailiuk, P. K. Chem. Rev. 2021, 121, 1670.

    Article  CAS  PubMed  Google Scholar 

  8. Jeschke, P. Eur. J. Org. Chem. 2022, e202101513.

  9. Li, F.; Wang, M.; Liu, S.; Zhao, Q. Chem. Sci. 2022, 13, 2184.

    Article  CAS  PubMed  Google Scholar 

  10. Bremer, M.; Kirsch, P.; Klasen-Memmer, M.; Tarumi, K. Angew. Chem., Int. Ed. 2013, 52, 8880.

  11. Squeo, B. M.; Gregoriou, V. G.; Avgeropoulos, A.; Baysec, S.; Allardd, S.; Scherf, U.; Chochos, C. L. Prog. Polym. Sci. 2017, 71, 26.

    Article  CAS  Google Scholar 

  12. Mashkovskii, M. D. Lekarstvennye sredstva (Drugs) [in Russian]; Moscow: Novaya volna, 2002, 14th ed., Vol. 1, 2.

  13. Cros, A.; Alfaro-Espinoza, G.; De Maria, A.; Wirth, N. T.; Nikel, P. I. Curr. Opin. Biotechnol. 2022, 74, 180.

    Article  CAS  PubMed  Google Scholar 

  14. Preshlock, S.; Tredwell, M.; Gouverneur, V. Chem. Rev. 2016, 116, 719.

    Article  CAS  PubMed  Google Scholar 

  15. Iskra, J. In Halogenated Heterocycles. Synthesis, Application and Environment; Iskra, J., Ed.; Springer-Verlag: Berlin, Heidelberg, 2012, p. 269.

  16. Borodkin, G. I.; Shubin, V. G. Russ. J. Org. Chem. 2021, 57, 1369.

    Article  CAS  Google Scholar 

  17. Borodkin, G. I.; Shubin, V. G. Chem. Heterocycl. Compd. 2022, 58, 84.

    Article  CAS  Google Scholar 

  18. Manley J. B. In Scalable Green Chemistry: Case Studies from the Pharmaceutical Industry; Koenig, S. G., Ed.; Jenny Stanford Publishing: New York, 2013, p. 1.

  19. Erythropel, H. C.; Zimmerman, J. B.; de Winter, T. M.; Petitjean, L.; Melnikov, F.; Lam, C. H.; Lounsbury, A. W.; Mellor, K. E.; Janković, N. Z.; Tu, Q.; Pincus, L. N.; Falinski, M. M.; Shi, W.; Coish, P.; Plata, D. L.; Anastas, P. T. Green Chem. 2018, 20, 1929.

    Google Scholar 

  20. Sheldon, R. A. Pure Appl. Chem. 2000, 72, 1233.

    Article  CAS  Google Scholar 

  21. Gomollón-Bel, F. Chem. Int. 2019, 41, 12.

    Article  Google Scholar 

  22. Howard, J. L.; Cao, Q.; Browne, D. L. Chem. Sci. 2018, 9, 3080.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Štrukil, V. Synlett 2018, 1281.

  24. Obst, M.; König, B. Eur. J. Org. Chem. 2018, 4213.

  25. Pérez-Venegas, M.; Juaristi, E. ACS Sustainable Chem. Eng. 2020, 8, 8881.

    Article  Google Scholar 

  26. Takacs, L. Chem. Soc. Rev. 2013, 42, 7649.

    Article  CAS  PubMed  Google Scholar 

  27. Hwang, S.; Grätz, S.; Borchardt, L. Chem. Commun. 2022, 58, 1661.

    Article  CAS  Google Scholar 

  28. Wang, G.-W. Chem. Soc. Rev. 2013, 42, 7668.

    Article  CAS  PubMed  Google Scholar 

  29. El-Sayed, T. H.; Aboelnaga, A.; El-Atawy, M. A.; Hagar, M. Molecules 2018, 23, 1348.

    Article  PubMed  PubMed Central  Google Scholar 

  30. Margetić, D.; Štrukil, V. In Organic Synthesis – A Nascent Relook; Nandeshwarappa, B. P., Ed.; IntechOpen: London, 2020, p. 27.

    Google Scholar 

  31. Leonardi, M.: Villacampa M.; Menéndez, J. C. Chem. Sci. 2018, 9, 2042.

  32. Borodkin, G. I.; Shubin, V. G. Russ. Chem. Rev. 2010, 79, 259.

    Article  CAS  Google Scholar 

  33. McPake, C. B.; Sandford, G. Org. Process Res. Dev. 2012, 16, 844.

    Article  CAS  Google Scholar 

  34. Tang, R.-J.; Milcent, T.; Crousse, B. J. Org. Chem. 2018, 83, 930.

    Article  CAS  PubMed  Google Scholar 

  35. Yuan, Y.; Yao, A.; Zheng, Y.; Gao, M.; Zhou, Z.; Qiao, J.; Hu, J.; Ye, B.; Zhao, J.; Wen, H.; Lei, A. iScience 2019, 12, 293.

    Article  CAS  PubMed  Google Scholar 

  36. Wang, Y.; Wang, H.; Jiang, Y.; Zhang, C.; Shao, J.; Xu, D. Green Chem. 2017, 19, 1674.

    Article  CAS  Google Scholar 

  37. Zaikin, P. A.; Dyan, O. T.; Elanov, I. R.; Borodkin, G. I. Molecules 2021, 26, 5756.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  38. Howard, J. L.; Nicholson, W.; Sagatov, Y.; Browne, D. L. Beilstein J. Org. Chem. 2017, 13, 1950.

    Google Scholar 

  39. Krištofíková, D.; Mečiarová, M.; Rakovský, E.; Šebesta, R. ACS Sustainable Chem. Eng. 2020, 38, 14417.

    Article  Google Scholar 

  40. Riley, W.; Jones, A. C.; Singh, K.; Browne, D. L.; Stuart, A. M. Chem. Commun. 2021, 57, 7406.

    Article  CAS  Google Scholar 

  41. Neogi, I.; Das, P. J.; Grynszpan, F. Synlett 2018, 1043.

  42. Nagarajaiah, H.; Mishra, A. K.; Moorthy, J. N. Org. Biomol. Chem. 2016, 14, 4129.

    Article  CAS  PubMed  Google Scholar 

  43. Bera, S. K.; Mal, P. J. Org. Chem. 2021, 86, 14144.

    Article  CAS  PubMed  Google Scholar 

  44. Indukuri, D. R.; Potuganti, G. R.; Alla, M. Synlett 2019, 1573.

  45. Das, D.; Bhosle, A. A.; Chatterjee, A.; Banerjee, M. Beilstein J. Org. Chem. 2022, 18, 999.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  46. Mishra, A. K.; Nagarajaiah, H., Moorthy, J. N. Eur. J. Org. Chem. 2015, 2733.

  47. Martins, I. C. B.; Carta, M.; Haferkamp, S.; Feiler, T.; Delogu, F.; Colacino, E.; Emmerling, F. ACS Sustainable Chem. Eng. 2021, 37, 12591.

    Article  Google Scholar 

  48. Bal, A.; Dinda, T. K.; Mal, P. Asian J. Org. Chem. 2022, 11, e202200046.

    CAS  Google Scholar 

  49. Wong, J.; Yeung, Y.-Y. RSC Adv. 2021, 11, 13564.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  50. Hernáґndez, J. G.; Bolm, C. Chem. Commun. 2015, 51, 12582.

    Article  Google Scholar 

  51. Sereda, G.; Sarkar, A. M.; Hussain, A.; Zefirov, N. Synthesis 2020, 1140.

  52. Mantovani, A. C.; Hernandez, J. G.; Bolm, C. Eur. J. Org. Chem. 2018, 2458.

  53. Halder, A.; Maiti, D.; Sarkar, S. D. Chem.–Asian J. 2020, 15, 577.

  54. Egorov, I. N.; Santra, S.; Kopchuk, D. S.; Kovalev, I. S.; Zyryanov, G. V.; Majee, A.; Ranu, B. C.; Rusinov, V. L.; Chupakhin, O. N. Green Chem. 2020, 22, 302.

    Article  CAS  Google Scholar 

  55. Williams, M. T. J.; Morrill, L. C.; Browne, D. L. ChemSusChem 2022, 15, e202102157.

    Article  CAS  PubMed  Google Scholar 

  56. Zhao, S.; Li, Y.; Liu, C.; Zhao. Y. Tetrahedron Lett. 2018, 59, 317.

    Article  CAS  Google Scholar 

  57. Zaikin, P. A.; Dyan, O. T.; Evtushok, D. V.; Usoltsev, A. N.; Borodkin, G. I.; Karpova, E. V.; Shubin, V. G. Eur. J. Org. Chem. 2017, 2469.

  58. Martinez, V.; Stolar, T.; Karadeniz, B.; Brekalo, I.; Užarević, K. Nature Rev. Chem. 2023, 7, 51.

    Article  CAS  Google Scholar 

  59. Liu, X.; Li, Y.; Zeng, L.; Li, X.; Chen, N.; Bai, S.; He, H.; Wang, Q.; Zhang, C. Adv. Mater. 2022, 34, 2108327.

    Article  CAS  Google Scholar 

  60. Gawande, M. B.; Bonifácio, V. D. B.; Luque, R.; Branco, P. S.; Varma, R. S. ChemSusChem 2014, 7, 24.

    Article  CAS  PubMed  Google Scholar 

  61. Friščić, T.; Mottillo, C.; Titi, H. M. Angew. Chem., Int. Ed. 2020, 59, 1018.

  62. Stauch, T.; Dreuw, A. Acc. Chem. Res. 2017, 50, 1041.

    Article  CAS  PubMed  Google Scholar 

  63. Lapshin, O. V.; Boldyreva, E. V.; Boldyrev, V. V. Russ. J. Inorg. Chem. 2021, 66, 433.

    Article  CAS  Google Scholar 

  64. Kulla, H.; Haferkamp, S.; Akhmetova, I.; Röllig, M.; Maierhofer, C.; Rademann, K.; Emmerling, F. Angew. Chem., Int. Ed. 2018, 57, 5930.

  65. Friščić, T.; Halasz, I.; Beldon, P. J.; Belenguer, A. M.; Adams, F.; Kimber, S. A. J.; Honkimäki, V.; Dinnebier, R. E. Nature Chem. 2013, 5, 66.

    Article  Google Scholar 

  66. Lapshin, O. V.; Boldyrev, V. V.; Boldyreva, E. V. Russ. J. Phys. Chem. A 2021, 95, 2310.

    Article  CAS  Google Scholar 

  67. Pladevall, B. S.; de Aguirre, A.; Maseras, F. ChemSusChem 2021, 14, 2763.

    Article  CAS  PubMed  Google Scholar 

  68. Wollenhaupt, M.; Krupicka, M.; Marx, D. ChemPhysChem 2015, 16, 1565.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave, Novosibirsk, 630090, Russia

    Gennady I. Borodkin

  2. Novosibirsk State University, 1 Pirogova St, Novosibirsk, 630090, Russia

    Gennady I. Borodkin

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Correspondence to Gennady I. Borodkin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(8), 525–533

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Borodkin, G.I. Mechanochemical synthesis of halogenated heterocyclic compounds. Chem Heterocycl Comp 59, 525–533 (2023). https://doi.org/10.1007/s10593-023-03227-6

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