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Multicomponent transformation of salicylaldehydes, 2-aminoprop-1-ene-1,1,3-tricarbonitrile, and pyrazolin-5-ones into substituted 2,4-diamino-5-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitriles

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Russian Chemical Bulletin Aims and scope

Abstract

A new multicomponent reaction, namely, a one-pot transformation of salicylaldehydes, 2-aminoprop-1-ene-1,1,3-tricarbonitrile, and 2-pyrazolin-5-ones in the presence of triethylamine as the catalyst in a minimum amount of propanol leads to the previously unknown substituted 2,4-diamino-5-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-5H-chromeno [2,3-b]- pyridine-3-carbonitriles in 63–98% yields. This reaction provides a facile and efficient route to a new type of functionalized 5-C-substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine systems containing the 2-pyrazolin-5-one moiety. These reaction products are promising compounds for different biomedical applications.

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References

  1. Multicomponent Reactions in Organic Synthesis, Eds J. Zhu, Q. Wang, M. Wang, Wiley-VCH, Weinheim, 2015.

  2. R. C. Cioc, E. Ruijter, R. V. Orru, Green Chem., 2014, 16, 2958.

    Article  CAS  Google Scholar 

  3. A. N. Vereshchagin, Russ. Chem. Bull., 2017, 66, 1765.

    Article  CAS  Google Scholar 

  4. M. Baumann, I. R. Baxendale, Beilstein J. Org. Chem., 2013, 9, 2265.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. S. Rajasekhar, B. Maiti, K. Chanda, Synlett., 2017, 28,521.

    Article  CAS  Google Scholar 

  6. D. S. Weinstein, H. Gong, A. M. Doweyko, M. Cunningham, S. Habte, J. H. Wang, D. A. Holloway, C. Burke, L. Gao, V. Guarino, J. Carman, J. E. Somerville, D. Shuster, L. Salter-Cid, J. H. Dodd, S. G. Nadler, J. C. Barrish, J. Med. Chem., 2011, 54, 7318.

    Article  CAS  PubMed  Google Scholar 

  7. G. Kolokythas, N. Pouli, P. Marakos, H. Pratsinis, D. Kletsas, Eur. J. Med. Chem., 2006, 41,71.

    Article  CAS  PubMed  Google Scholar 

  8. M. A. Azuine, H. Tokuda, J. Takayasu, F. Enjyo, G. J. Kapadia, J. Pharmacol. Res., 2004, 49,161.

    Article  CAS  Google Scholar 

  9. Y. Maruyama, K. Goto, M. Terasawa, Ger. Offen. DE 3010751, 1981.

  10. Y. Ito, H. Kato, S. Yasuda, N. Kato, N. Iwasaki, H. Nishino, M. Takeshita, JP 6107664, 1994.

  11. K. Ukawa, T. Ishiguro, H. Kuriki, A. Nohara, Chem. Pharm. Bull., 1985, 33, 4432.

    Article  CAS  PubMed  Google Scholar 

  12. S. K. Srivastava, R. P. Tripathi, R. J. Ramachandran, J. Biol. Chem., 2005, 280, 30273.

    Article  CAS  PubMed  Google Scholar 

  13. D. R. Anderson, S. Hegde, E. Reinhard, L. Gomez, W. F. Vernier, L. Lee, S. Liu, A. Sambandam, P. A. Snider, L. Masih, Bioorg. Med. Chem. Lett., 2005, 15, 1587.

    Article  CAS  PubMed  Google Scholar 

  14. J. Elguero, P. Goya, N. Jagerovic, A. M. S. Silva, Pyrazoles as Drugs. Italian Society of Chemistry, Rome, 2002.

    Google Scholar 

  15. F. Lepage, B. Hubiot, Eur. Pat. Appl., 459887, 1992.

    Google Scholar 

  16. K. L. Kees, J. J. Fitzgerald, K. E. Steiner, J. F. Mattes, B. Mihan, T. Tosi, D. Mondoro, M. L. McCaleb, J. Med. Chem., 1996, 39, 3920.

    Article  CAS  PubMed  Google Scholar 

  17. L. D. Wise, D. E. Butler, H. A. DeWald, D. M. Lustgarten, I. C. Pattison, D. N. Schweiss, L. L. Coughenour, D. A. Downs, T. G. Heffner, T. A. Pugsley, J. Med. Chem., 1987, 30, 1807.

    Article  CAS  PubMed  Google Scholar 

  18. T. van Herk, J. Brussee, A. M. C. H. van den Nieuwendijk, P. A. M. van der Klein, A. P. Jzerman, C. Stannek, A. Burmeister, A. Lorenzen, J. Med. Chem., 2003, 46, 3945.

    Article  CAS  PubMed  Google Scholar 

  19. P. Singh, K. Paul, W. Holzer, Bioorg. Med. Chem., 2006, 14, 5061.

    Article  CAS  PubMed  Google Scholar 

  20. M. N. Elinson, A. I. Ilovaisky, V. M. Merkulova, T. A. Zaimovskaya, G. I. Nikishin, Mendeleev Commun., 2012, 22,143.

    Article  CAS  Google Scholar 

  21. M. N. Elinson, A. I. Ilovaisky, V. M. Merkulova, P. A. Belyakov, F. Barba, B. Batanero, Tetrahedron, 2012, 68, 5833.

    Article  CAS  Google Scholar 

  22. M. N. Elinson, A. I. Ilovaisky, V. M. Merkulova, F. Barba, B. Batanero, Tetrahedron, 2013, 69, 7125.

    Article  CAS  Google Scholar 

  23. M. N. Elinson, R. F. Nasybullin, F. V. Ryzhkov, M. M. Egorov, C. R. Chimie, 2014, 17,437.

    Article  CAS  Google Scholar 

  24. M. N. Elinson, F. V. Ryzhkov, V. A. Korolev, M. P. Egorov, Heterocyclic Commun., 2016, 22,11.

    Article  CAS  Google Scholar 

  25. M. N. Elinson, F. V. Ryzhkov, A. N. Vereshchagin, Mendeleev Commun., 2017, 27,559.

    Article  CAS  Google Scholar 

  26. A. N. Vereshchagin, M. N. Elinson, Y. E. Anisina, F. V. Ryzhkov, A. S. Goloveshkin, I. S. Bushmarinov, S. G. Zlotin, M. P. Egorov, Mendeleev Commun., 2015, 25,424.

    Article  CAS  Google Scholar 

  27. A. N. Vereshchagin, M. N. Elinson, Y. E. Anisina, F. V. Ryzhkov, A. S. Goloveshkin, R. A. Novikov, M. P. Egorov, J. Mol. Str., 2017, 1146,766.

    Article  CAS  Google Scholar 

  28. R. A. Sheldon, I. W. C. E. Arends, U. Hanefeld, Green Chemistry and Catalysis, Wiley-VHC, Weinheim, 2007.

    Book  Google Scholar 

  29. K. Tanaka, F. Toda, Chem. Rev., 2000, 100, 1025.

    Article  CAS  PubMed  Google Scholar 

  30. M. N. Elinson, M. G. Medvedev, A. I. Ilovaisky, V. M. Merkulova, T. A. Zaimovskaya, G. I. Nikishin, Mendeleev Commun., 2013, 23,94.

    Article  CAS  Google Scholar 

  31. R. N. Butler, A. G. Coyne, Org. Biomol. Chem., 2016, 14, 9945.

    Article  CAS  PubMed  Google Scholar 

  32. D. V. Demchuk, M. N. Elinson, G. I. Nikishin, Mendeleev. Commun., 2011, 21,224.

    Article  CAS  Google Scholar 

  33. G. A. Bowmaker, Chem. Commun., 2013, 49,334.

    Article  CAS  Google Scholar 

  34. A. Sarkar, S. Santra, S. K. Kundu, A. Hajra, G. V. Zyryanov, O. N. Chupakhin, V. N. Charushin, A. Majee, Green Chem., 2016, 18, 4475.

    Article  CAS  Google Scholar 

  35. M. N. Elinson, F. V. Ryzhkov, R. F. Nasybullin, T. A. Zaimovskaya, M. P. Egorov, Mendeleev Commun., 2014, 24,170.

    Article  CAS  Google Scholar 

  36. A. N. Vereshchagin, M. N. Elinson, R. F. Nasybullin, F. V. Ryzhkov, S. I. Bobrovsky, I. S. Bushmarinov, M. P. Egorov, Helv. Chim. Acta, 2015, 98, 1104.

    Article  CAS  Google Scholar 

  37. M. N. Elinson, F. V. Ryzhkov, A. N. Vereshchagin, T. A. Zaimovskaya, V. A. Korolev, M. P. Egorov, Mendeleev Commun., 2016, 26,399.

    Article  CAS  Google Scholar 

  38. M. N. Elinson, S. V. Gorbunov, A. N. Vereshchagin, R. F. Nasybullin, A. S. Goloveshkin, I. S. Bushmarinov, M. P. Egorov, Tetrahedron, 2014, 70, 8559.

    Article  CAS  Google Scholar 

  39. M. N. Elinson, A. I. Ilovaisky, V. M. Merkulova, P. A. Belyakov, A. O. Chizhov, G. I. Nikishin, Tetrahedron, 2010, 66, 4043.

    Article  CAS  Google Scholar 

  40. S. Patai, Y. Israeli, J. Chem. Soc., 1960, 2025.

    Google Scholar 

  41. M. Mittelbach, Monatsh. Chem., 1985, 116,689.

    Article  CAS  Google Scholar 

  42. Bruker, TOPAS 4.2 User Manual, Bruker AXS GmbH, Karlsruhe, Germany, 2009.

  43. V. Favre-Nicolin, R. Cerný, J. Appl. Crystallogr., 2002, 35,734.

    Article  CAS  Google Scholar 

  44. I. S. Bushmarinov, A. O. Dmitrienko, A. A. Korlyukov, M. Y. Antipin, J. Appl. Crystallogr., 2012, 45, 1187.

    Article  CAS  Google Scholar 

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Authors and Affiliations

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

    M. N. Elinson, A. N. Vereshchagin, Y. E. Anisina & M. P. Egorov

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    A. S. Goloveshkin & I. E. Ushakov

Authors
  1. M. N. Elinson
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  2. A. N. Vereshchagin
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  3. Y. E. Anisina
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  4. A. S. Goloveshkin
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  5. I. E. Ushakov
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  6. M. P. Egorov
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Correspondence to M. N. Elinson.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1695–1703, September, 2018.

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Elinson, M.N., Vereshchagin, A.N., Anisina, Y.E. et al. Multicomponent transformation of salicylaldehydes, 2-aminoprop-1-ene-1,1,3-tricarbonitrile, and pyrazolin-5-ones into substituted 2,4-diamino-5-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitriles. Russ Chem Bull 67, 1695–1703 (2018). https://doi.org/10.1007/s11172-018-2278-1

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  • DOI: https://doi.org/10.1007/s11172-018-2278-1

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