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Synthesis of functionalyzed imidazo[1,2-a]pyridines via domino A3-coupling/cycloisomerization approach

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Chemistry of Heterocyclic Compounds Aims and scope

Recent developments in the synthesis of imidazo[1,2-a]pyridines via the transition metal-catalyzed three-component heterocyclization of aldehyde, 2-aminopyridine, and alkyne are discussed in this highlight.

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References

  1. Dymin'ska, L. Bioorg. Med. Chem. 2015, 23, 6087.

    Article  Google Scholar 

  2. Gunja, N. J. Med. Tox. 2013, 9, 163.

    Article  CAS  Google Scholar 

  3. Harrison, T. S.; Keating, G. M. CNS Drugs 2005, 19, 65.

    Article  CAS  Google Scholar 

  4. Enguehard-Gueiffier, C.; Gueiffier, A. Mini-Rev. Med. Chem. 2007, 7, 888.

    Article  CAS  Google Scholar 

  5. Prostota, Y.; Kachkovsky, O. D.; Reis, L. V.; Santos, P. F. Dyes Pigm. 2013, 96, 554.

    Article  CAS  Google Scholar 

  6. Ke, C.-H.; Kuo, B.-C.; Nandi, D.; Lee, H. M. Organometallics 2013, 32, 4775.

    Article  CAS  Google Scholar 

  7. Bagdi, A. K.; Santra, S.; Monir, K.; Hajra, F. Chem. Commun. 2015, 51, 1555.

    Article  CAS  Google Scholar 

  8. Guetzoyan, L.; Nikbin, N.; Baxendale, I. R.; Ley, S. V. Chem. Sci. 2013, 4, 764.

    Article  CAS  Google Scholar 

  9. Enguehard, C.; Renou, J.-L.; Allouchi, H.; Leger, J.-M.; Gueiffier, A. Chem. Pharm. Bull. 2000, 48, 935.

    Article  CAS  Google Scholar 

  10. Osakada, N.; Kaneko, S.; Mizutani, A.; Uesaka, N.; Katayama, K. EP Patent 2070927.

  11. Thomas, A. P.; Allott, C. P.; Gibson, K. H.; Major, J. S.; Masek, B. B.; Oldham, A. A.; Ratcliffe, A. H.; Roberts, D. A.; Russell, S. T.; Thomason, D. A. J. Med. Chem. 1992, 35, 877.

    Article  CAS  Google Scholar 

  12. Lu, Z.; Ott, G. R.; Anand, R.; Liu, R.-Q.; Covington, M. B.; Vaddi, K.; Qian, M.; Newton, R. C.; Christ, D. D.; Trzaskos, J.; Duan, J. J.-W. Bioorg. Med. Chem. Lett. 2008, 18, 1958.

    Article  CAS  Google Scholar 

  13. Kaplan, J.-P.; George, P. US Patent 4382938.

  14. Zaworska, A.; Dzikowska, J.; Cybulski, J.; Bankowski, K.; Szelejewski, W. PL Patent 196300.

  15. Chinnapillai, R.; Nallamaddi, R. R.; Arava, V. R.; Jasti, V. WO Patent 2009007995.

  16. Labriola, R. WO Patent 2000008021.

  17. Santra, S.; Bagdi, A. K.; Majee, A.; Hajra, A. Adv. Synth. Catal. 2013, 355, 1065.

    Article  CAS  Google Scholar 

  18. Yan, H.; Wang, Y.; Pan, C.; Zhang, H.; Yang, S.; Ren, X.; Li, J.; Huang, G. Eur. J. Org. Chem. 2014, 2754.

  19. Schwerkoske, J.; Masquelin, T.; Perun, T.; Hulme, C. Tetrahedron Lett. 2005, 46, 8355.

    Article  CAS  Google Scholar 

  20. Rousseau, A. L.; Matlaba, P.; Parkinson, C. J. Tetrahedron Lett. 2007, 48, 4079.

    Article  CAS  Google Scholar 

  21. Peshkov, V. A.; Pereshivko, O. P.; Van der Eycken, E. V. Chem. Soc. Rev. 2012, 41, 3790.

    Article  CAS  Google Scholar 

  22. Chernyak, N.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 2743.

    Article  CAS  Google Scholar 

  23. Palani, T.; Park, K.; Kumar, M. R.; Jung, H. M.; Lee, S. Eur. J. Org. Chem. 2012, 5038.

  24. Rassokhina, I. V.; Volkova, Y. A.; Kozlov, A. S.; Scherbakov, A. M.; Andreeva, O. E.; Shirinian, V. Z.; Zavarzin, I. V. Steroids 2016, 113, 29.

    Article  CAS  Google Scholar 

  25. Mishra, S.; Ghosh, R. Synthesis 2011, 3463.

  26. Liu, P.; Fang, L.-s.; Lei, X.; Lin, G.-q. Tetrahedron Lett. 2010, 51, 4605.

  27. Guchhait, S. K.; Chandgude, A. L.; Priyadarshani, G. J. Org. Chem. 2012, 77, 4438.

    Article  CAS  Google Scholar 

  28. Rassokhina, I. V.; Shirinian, V. Z.; Zavarzin, I. V.; Gevorgyan, V.; Volkova, Y. A. J. Org. Chem. 2015, 80, 11212.

    Article  CAS  Google Scholar 

  29. Bharate, J. B.; Guru, S. K.; Jain, S. K.; Meena, S.; Singh, P. P.; Bhushan, S.; Singh, B.; Bharateab, S. B.; Vishwakarma, R. A. RSC Adv. 2013, 3, 20869.

    Article  CAS  Google Scholar 

  30. Luz, I.; Xamena, F. X. L.; Corma, A. J. Catal. 2012, 285, 285.

    Article  CAS  Google Scholar 

  31. Tajbakhsh, M.; Farhang, M.; Hosseinzadeh, R.; Sarrafi, Y. RSC Adv. 2014, 4, 23116.

    Article  CAS  Google Scholar 

  32. Bagdi, P. R.; Basha, R. S.; Khan, A. T. RSC Adv. 2015, 5, 61337.

    Article  CAS  Google Scholar 

  33. Mandlimath, T. R.; Sathiyanarayanan, K. I. RSC Adv. 2016, 6, 3117.

    Article  CAS  Google Scholar 

  34. Reddy, B. V. S.; Reddy, P. S.; Reddy, Y. J.; Yadav, J. S. Tetrahedron Lett. 2011, 52, 5789.

    Article  CAS  Google Scholar 

  35. Siddiqui, I. R.; Rai, P.; Rahila; Srivastava, A.; Shamim, S. Tetrahedron Lett. 2014, 55, 1159.

  36. Guntreddi, T.; Allam, B. K.; Singh, K. N. Synlett 2012, 2635.

  37. Maleki, A. Helv. Chem. Acta 2014, 97, 587.

    Article  CAS  Google Scholar 

  38. Palani, T.; Park, K.; Kumar, M. R.; Jung, H. M.; Lee, S. Eur. J. Org. Chem. 2012, 5038.

  39. Selvaraju, M.; Ye, T.-Y.; Li, C.-H.; Ho, P.-H.; Sun, C.-M. Chem. Commun. 2016, 52, 6621.

    Article  CAS  Google Scholar 

  40. Nagarajan, N.; Velmurugan, G.; Prakash, A.; Shakti, N.; Katiyar, M.; Venuvanalingam, P.; Renganathan, R. Chem. Asian J. 2014, 9, 294.

    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 Ave., Moscow, 119991, Russia

    Yulia Volkova

  2. Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL, 60607, USA

    Vladimir Gevorgyan

Authors
  1. Yulia Volkova
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  2. Vladimir Gevorgyan
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Corresponding authors

Correspondence to Yulia Volkova or Vladimir Gevorgyan.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(4), 409–412

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Volkova, Y., Gevorgyan, V. Synthesis of functionalyzed imidazo[1,2-a]pyridines via domino A3-coupling/cycloisomerization approach. Chem Heterocycl Comp 53, 409–412 (2017). https://doi.org/10.1007/s10593-017-2066-0

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  • DOI: https://doi.org/10.1007/s10593-017-2066-0

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