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Reactivity of 2-aminopyridine N-oxides

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Abstract

The main aspects of the reactivity of 2-aminopyridine N-oxides and similar heterocyclic systems are discussed. Literature data are systematized based on the types of transformations considered with a focus on the major advantages and disadvantages of each synthetic method. The possibility to synthesize previously inaccessible functionally substituted and bicyclic pyridine derivatives based on selective transformations of 2-aminopyridine N-oxides is demonstrated.

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References

  1. N. N. Makhova, L. I. Belen’kii, G. A. Gazieva, I. L. Dalinger, L. S. Konstantinova, V. V. Kuznetsov, A. N. Kravchenko, M. M. Krayushkin, O. A. Rakitin, A. M. Starosotnikov, L. L. Fershtat, S. A. Shevelev, V. Z. Shirinian, V. N. Yarovenko, Russ. Chem. Rev., 2020, 89, 55; DOI: https://doi.org/10.1070/RCR4914.

    Article  ADS  CAS  Google Scholar 

  2. S. G. Zlotin, A. M. Churakov, M. P. Egorov, L. L. Fershtat, M. S. Klenov, I. V. Kuchurov, N. N. Makhova, G. A. Smirnov, Yu. V. Tomilov, V. A. Tartakovsky, Mendeleev Commun., 2021, 31, 731; DOI: https://doi.org/10.1016/j.mencom.2021.11.001.

    Article  CAS  Google Scholar 

  3. A. A. Larin, L. L. Fershtat, Mendeleev Commun., 2022, 32, 703; DOI: https://doi.org/10.1016/j.mencom.2022.11.001.

    Article  CAS  Google Scholar 

  4. D. M. Bystrov, L. L. Fershtat, N. N. Makhova, Chem. Heterocycl. Compd., 2019, 55, 1143; DOI: https://doi.org/10.1007/s10593-019-02593-4.

    Article  CAS  Google Scholar 

  5. P. Koukal, J. Ulč, D. Nečas, M. Kotora, in Heterocyclic N-Oxides, Ed. O. V. Larionov, Springer-Verlag, Berlin, 2017, p. 29; DOI: https://doi.org/10.1007/978-3-319-60687-3.

  6. I. Habib, K. Singha, M. Hossain, ChemistrySelect, 2023, 8, e202204099; DOI: https://doi.org/10.1002/slct.202204099.

    Article  CAS  Google Scholar 

  7. D. F. Chen, Z. Y. Han, Y. P. He, J. Yu, L. Z. Gong, Angew. Chem., Int. Ed., 2012, 51, 12307; DOI: https://doi.org/10.1002/anie.201205062.

    Article  CAS  Google Scholar 

  8. T. J. Donohoe, K. M. Wheelhouse, P. J. Lindsay-Scott, P. A. Glossop, I. A. Nash, J. S. Parker, Angew. Chem., Int. Ed., 2008, 47, 2872; DOI: https://doi.org/10.1002/anie.200705425.

    Article  CAS  Google Scholar 

  9. J. Balzarini, M. Stevens, E. De Clercq, D. Schols, C. Pannecouque, J. Antimicrob. Chemother., 2005, 55, 135; DOI: https://doi.org/10.1093/jac/dkh530.

    Article  CAS  PubMed  Google Scholar 

  10. M. Stevens, C. Pannecouque, E. De Clercq, J. Balzarini, Biochem. Pharmacol., 2006, 71, 1122; DOI: https://doi.org/10.1016/j.bcp.2005.12.025.

    Article  CAS  PubMed  Google Scholar 

  11. R. Shevate, M. Karunakaran, M. Kumar, K. V. Peinemann, J. Membr. Sci., 2016, 501, 161; DOI: https://doi.org/10.1016/j.memsci.2015.11.038.

    Article  CAS  Google Scholar 

  12. A. S. Munn, S. Amabilino, T. W. Stevens, L. M. Daniels, G. J. Clarkson, F. Millange, M. J. Lennox, T. Düren, S. Bourelly, P. L. Llewellyn, R. I. Walton, Cryst. Growth Des., 2015, 15, 891; DOI: https://doi.org/10.1021/cg501690b.

    Article  CAS  Google Scholar 

  13. F. Pointillart, T. Cauchy, Y. Le Gal, S. Golhen, O. Cador, L. Ouahab, Chem. Commun., 2010, 46, 4947; DOI: https://doi.org/10.1039/C0CC00672F.

    Article  CAS  Google Scholar 

  14. A. Palani, S. Shapiro, H. Josien, T. Bara, J. W. Clader, W. J. Greenlee, K. Cox, J. M. Strizki, B. M. Baroudy, J. Med. Chem., 2002, 45, 3143; DOI: https://doi.org/10.1021/jm0200815.

    Article  CAS  PubMed  Google Scholar 

  15. W. Z. Antkowiak, W. P. Gessner, Tetrahedron Lett., 1979, 20, 1931; DOI: https://doi.org/10.1016/S0040-4039(01)86882-9.

    Article  Google Scholar 

  16. A. Herrmann, H. Hedman, J. Rosén, D. Jansson, B. Haraldsson, K. E. Hellenäs, J. Nat. Prod., 2012, 75, 1690; DOI: https://doi.org/10.1021/np300135k.

    Article  CAS  PubMed  Google Scholar 

  17. R. A. Hollins, L. H. Merwin, R. A. Nissan, W. S. Wilson, R. Gilardi, J. Heterocycl. Chem., 1996, 33, 895; DOI: https://doi.org/10.1002/jhet.5570330357.

    Article  CAS  Google Scholar 

  18. R. Tomar, A. Kumar, A. Dalal, D. Bhattacharya, P. Singh, S. Arulananda Babu, Asian J. Org. Chem., 2022, 11, e202200311; DOI: https://doi.org/10.1002/ajoc.202200311.

    Article  CAS  Google Scholar 

  19. X. Q. Hao, L. J. Chen, B. Ren, L. Y. Li, X. Y. Yang, J. F. Gong, J. L. Niu, M. P. Song, Org. Lett., 2014, 16, 1104; DOI: https://doi.org/10.1021/ol500166d.

    Article  CAS  PubMed  Google Scholar 

  20. M. Kumar, S. Verma, P. K. Mishra, A. K. Verma, J. Org. Chem., 2019, 84, 8067; DOI: https://doi.org/10.1021/acs.joc.9b00931.

    Article  CAS  PubMed  Google Scholar 

  21. M. Deb, J. Singh, S. Mallik, S. Hazra, A. J. Elias, New J. Chem., 2017, 41, 14528; DOI: https://doi.org/10.1039/C7NJ02388J.

    Article  CAS  Google Scholar 

  22. A. J. Rybarczyk-Pirek, M. Łukomska-Rogala, K. Wzgarda-Raj, S. Wojtulewski, M. Palusiak, Cryst. Growth Des., 2018, 18, 7373; DOI: https://doi.org/10.1021/acs.cgd.8b01057.

    Article  CAS  Google Scholar 

  23. R. Mei, H. Wang, S. Warratz, S. A. Macgregor, L. Ackermann, Chem. Eur. J., 2016, 22, 6759; DOI: https://doi.org/10.1002/chem.201601101.

    Article  CAS  PubMed  Google Scholar 

  24. L. B. Zhang, X. Q. Hao, S. K. Zhang, Z. J. Liu, X. X. Zheng, J. F. Gong, J. L. Niu, M. P. Song, Angew. Chem., Int. Ed., 2015, 54, 272; DOI: https://doi.org/10.1002/anie.201409751.

    Article  CAS  Google Scholar 

  25. S. K. Zhang, X. Y. Yang, X. M. Zhao, P. X. Li, J. L. Niu, M. P. Song, Organometallics, 2015, 34, 4331; DOI: https://doi.org/10.1021/acs.organomet.5b00581.

    Article  CAS  Google Scholar 

  26. J. M. McGrath, M. D. Pluth, J. Org. Chem., 2014, 79, 11797; DOI: https://doi.org/10.1021/jo402500a.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. A. J. Duraiswamy, M. A. Lee, B. Madan, S. H. Ang, E. S. W. Tan, W. W. V. Cheong, Z. Ke, V. Pendharkar, L. J. Ding, Y. S. Chew, V. Manoharan, K. Sangthongpitag, J. Alam, A. Poulsen, S. Y. Ho, D. M. Virshup, T. H. Keller, J. Med. Chem., 2015, 58, 5889; DOI: https://doi.org/10.1021/acs.jmedchem.5b00507.

    Article  CAS  PubMed  Google Scholar 

  28. F. Pointillart, B. Le Guennic, S. Golhen, O. Cador, O. Maury, L. Ouahab, Chem. Commun., 2013, 49, 615; DOI: https://doi.org/10.1039/C2CC37635K.

    Article  CAS  Google Scholar 

  29. A. R. Katritzky, J. Chem. Soc., 1957, 191; DOI: https://doi.org/10.1039/JR9570000191.

  30. A. Ohsawa, H. Arai, H. Igeta, Chem. Pharm. Bull., 1980, 28, 3570; DOI: https://doi.org/10.1248/cpb.28.3570.

    Article  Google Scholar 

  31. D. Rousseau, A. Taurins, Can. J. Chem., 1977, 55, 3736; DOI: https://doi.org/10.1139/v77-526.

    Article  CAS  Google Scholar 

  32. L. Capuano, V. Diehl, Chem. Ber., 1976, 109, 723; DOI: https://doi.org/10.1002/cber.19761090234.

    Article  CAS  Google Scholar 

  33. T. Kato, H. Yamanaka, T. Niitsuma, K. Wagatsuma, M. Oizumi, Chem. Pharm. Bull., 1964, 12, 910; DOI: https://doi.org/10.1248/cpb.12.910.

    Article  CAS  Google Scholar 

  34. Y. Wang, T. Wang, X. Wang, L. Liu, G. Mao, Transition Met. Chem., 2021, 46, 29; DOI: https://doi.org/10.1007/s11243-020-00418-4.

    Article  CAS  Google Scholar 

  35. E. Wolinska, W. Pucko, J. Heterocycl. Chem., 2013, 50, 590; DOI: https://doi.org/10.1002/jhet.1536.

    Article  CAS  Google Scholar 

  36. A. Rykowski, W. Pucko, Acta Pol. Pharm., 1999, 56, 57; PMID: 10635352.

    CAS  PubMed  Google Scholar 

  37. D. M. Bystrov, E. S. Zhilin, L. L. Fershtat, A. A. Romanova, I. V. Ananyev, N. N. Makhova, Adv. Synth. Catal., 2018, 360, 3157; DOI: https://doi.org/10.1002/adsc.201800407.

    Article  CAS  Google Scholar 

  38. J. E. Baldwin, J. Chem. Soc., Chem. Commun., 1976, 734; DOI: https://doi.org/10.1039/C39760000734.

  39. S. A. Karalash, D. M. Bystrov, I. V. Ananyev, L. L. Fershtat, Chem. Heterocycl. Compd., 2021, 57, 1130; DOI: https://doi.org/10.1007/s10593-021-03031-0.

    Article  CAS  Google Scholar 

  40. Q. Guo, Y. Li, C. Zhang, Z. Huang, X. Wang, Y. Nie, Y. Li, Y. Liu, S. Yang, R. Xiang, Y. Fan, Med. Chem. Res., 2018, 27, 1666; DOI: https://doi.org/10.1021/acs.jmedchem.8b00209.

    Article  CAS  Google Scholar 

  41. E. Wolinska, Heterocycl. Commun., 2016, 22, 85; DOI: https://doi.org/10.1515/hc-2016-0001.

    Article  CAS  Google Scholar 

  42. Y. S. Lin, J. Park, J. W. De Schutter, X. F. Huang, A. M. Berghuis, M. Sebag, Y. S. Tsantrizos, J. Med. Chem., 2012, 55, 3201; DOI: https://doi.org/10.1021/jm201657x.

    Article  CAS  PubMed  Google Scholar 

  43. J. I. Degraw, H. Tagawa, J. Heterocycl. Chem., 1982, 19, 1461; DOI: https://doi.org/10.1002/jhet.5570190641.

    Article  CAS  Google Scholar 

  44. B. Iddon, H. Suschitzky, A. W. Thompson, E. Ager, J. Chem. Soc., Perkin Trans. 1, 1974, 2300; DOI: https://doi.org/10.1039/P19740002300.

  45. M. Nettekoven, C. Jenny, Org. Process Res. Dev., 2003, 7, 38; DOI: https://doi.org/10.1021/op020085j.

    Article  CAS  Google Scholar 

  46. R. Shetty, D. Nguyen, D. Flubacher, F. Ruggle, A. Schumacher, M. Kelly, E. Michelotti, Tetrahedron Lett., 2007, 48, 113; DOI: https://doi.org/10.1016/j.tetlet.2006.10.159.

    Article  CAS  Google Scholar 

  47. K. Gewald, U. Hain, Z. Chem., 1986, 26, 434; DOI: https://doi.org/10.1002/zfch.19860261205.

    Article  CAS  Google Scholar 

  48. R. Balicki, L. Kaczmarek, M. Malinowski, Synth. Commun., 1989, 19, 897; DOI: https://doi.org/10.1080/00397918908051009.

    Article  CAS  Google Scholar 

  49. A. H. Romero, H. Cerecetto, Eur. J. Org. Chem., 2020, 2020, 1853; DOI: https://doi.org/10.1002/ejoc.202000064.

    Article  CAS  Google Scholar 

  50. K. M. Engstrom, A. L. Baize, T. S. Franczyk, J. M. Kallemeyn, M. M. Mulhern, R. C. Rickert, S. Wagaw, J. Org. Chem., 2009, 74, 3849; DOI: https://doi.org/10.1021/jo9003772.

    Article  CAS  PubMed  Google Scholar 

  51. B. Zacharie, N. Moreau, C. Dockendorff, J. Org. Chem., 2001, 15, 5264; DOI: https://doi.org/10.1021/jo015649g.

    Article  Google Scholar 

  52. H. G. O. Becker, H. Böttcher, H. Haufe, J. Prakt. Chem., 1970, 312, 433; DOI: https://doi.org/10.1002/prac.19703120306.

    Article  CAS  Google Scholar 

  53. J. Kreicberga, E. Jecs, V. Kampars, Chem. Heterocycl. Compd., 2008, 44, 29; DOI: https://doi.org/10.1007/s10593-008-0013-9.

    Article  CAS  Google Scholar 

  54. R. A. Abramovitch, B. W. Cue, Jr., J. Am. Chem. Soc., 1976, 98, 1478; DOI: https://doi.org/10.1021/ja00422a034.

    Article  CAS  Google Scholar 

  55. B. D. Zlatopolskiy, H. P. Kroll, E. Melotto, A. de Meijere, Eur. J. Org. Chem., 2004, 2004, 4492; DOI: https://doi.org/10.1002/ejoc.200400480.

    Article  Google Scholar 

  56. E. A. Krasnokutskaya, A. A. Chudinov, V. D. Filimonov, Synthesis, 2018, 50, 1368; DOI: https://doi.org/10.1055/s-0036-1591738.

    Article  CAS  Google Scholar 

  57. J. Slouka, V. Bekárek, Collect. Czech. Chem. Commun., 1988, 53, 626; DOI: https://doi.org/10.1135/cccc19880626.

    Article  CAS  Google Scholar 

  58. S. Saeki, S. Kondo, T. Hayashi, M. Hamana, Chem. Pharm. Bull., 1984, 32, 1780; DOI: https://doi.org/10.1248/cpb.32.1780.

    Article  CAS  Google Scholar 

  59. E. P. Talbot, M. Richardson, J. M. McKenna, F. D. Toste, Adv. Synth. Catal., 2014, 356, 687; DOI: https://doi.org/10.1002/adsc.201300996.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  60. L. W. Deady, M. S. Slanborough, J. Heterocycl. Chem., 1979, 16, 187; DOI: https://doi.org/10.1002/jhet.5570160135.

    Article  CAS  Google Scholar 

  61. L. W. Deady, M. S. Stanborough, Aust. J. Chem., 1981, 34, 1295; DOI: https://doi.org/10.1071/CH9811295.

    Article  CAS  Google Scholar 

  62. O. D. Kinzel, R. G. Ball, M. Donghi, C. K. Maguire, E. Muraglia, S. Pesci, M. Rowley, V. Summa, Tetrahedron Lett., 2008, 49, 6556; DOI: https://doi.org/10.1016/j.tetlet.2008.09.010.

    Article  CAS  Google Scholar 

  63. J. Lu, N. S. Li, S. C. Koo, J. A. Piccirilli, J. Org. Chem., 2009, 74, 8021; DOI: https://doi.org/10.1021/jo9016919.

    Article  CAS  PubMed  Google Scholar 

  64. D. Hutter, S. A. Benner, J. Org. Chem., 2003, 68, 9839; DOI: https://doi.org/10.1021/jo034900k.

    Article  CAS  PubMed  Google Scholar 

  65. T. R. Kelly, G. J. Bridger, C. Zhao, J. Am. Chem. Soc., 1990, 112, 8024; DOI: https://doi.org/10.1021/ja00178a027.

    Article  CAS  Google Scholar 

  66. F. I. Carroll, T. P. Robinson, L. E. Brieaddy, R. N. Atkinson, S. W. Mascarella, M. I. Damaj, B. R. Martin, H. A. Navarro, J. Med. Chem., 2007, 50, 6383; DOI: https://doi.org/10.1021/jm0704696.

    Article  CAS  PubMed  Google Scholar 

  67. J. Bödeker, A. Köckritz, P. Köckritz, R. Radeglia, J. Prakt. Chem., 1985, 327, 723; DOI: https://doi.org/10.1002/prac.19853270504.

    Article  Google Scholar 

  68. E. V. Brown, J. Am. Chem. Soc., 1957, 79, 3565; DOI: https://doi.org/10.1021/ja01570a070.

    Article  CAS  Google Scholar 

  69. A. M. Starosotnikov, M. A. Bastrakov, V. A. Kokorekin, Russ. Chem. Bull., 2022, 71, 474; DOI: https://doi.org/10.1007/s11172-022-3435-0.

    Article  CAS  Google Scholar 

  70. Yu. A. Kvashnin, E. V. Verbitskiy, G. L. Rusinov, V. N. Charushin, Russ. Chem. Bull., 2022, 71, 1342; DOI: https://doi.org/10.1007/s11172-022-3540-0.

    Article  CAS  Google Scholar 

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Funding

Financial support from the Basic Research Program of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences is gratefully acknowledged.

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  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    D. M. Bystrov & L. L. Fershtat

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  1. D. M. Bystrov
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Correspondence to D. M. Bystrov.

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Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 73, No. 1, pp. 33–52, January, 2024.

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Bystrov, D.M., Fershtat, L.L. Reactivity of 2-aminopyridine N-oxides. Russ Chem Bull 73, 33–52 (2024). https://doi.org/10.1007/s11172-024-4120-2

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