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Aluminized polyborate: a novel catalyst for the multicomponent solvent-free synthesis of alkyl 1,2,6-trisubstituted-4-[(hetero)arylamino]-1,2,5,6-tetrahydropyridine-3-carboxylates

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Abstract

An efficient and simple method for the one-pot three-component synthesis of alkyl 1,2,6-trisubstituted-4-[(hetero)arylamino]-1,2,5,6-tetrahydropyridine-3-carboxylates was developed using aromatic aldehyde, amine and β-ketoesters catalyzed by aluminized polyborate, an efficient reusable catalyst under solvent-free condition. Aluminized polyborate has advantageous of cost, ecologically benefits, accessible preparation and recyclability up to five cycles along with high product yield and simplicity.

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References

  1. T.R. Bastami, M.H. Entezari, Ultrason. Sonochem. 19, 830 (2012)

    Article  CAS  Google Scholar 

  2. F.X. Felpin, J. Lebreton, Curr. Org. Synth. 1, 83 (2004)

    Article  CAS  Google Scholar 

  3. N. Howard, C. Abell, W. Blakemore, G. Chessari, M. Congreve, S. Howard, H. Jhoti, C.W. Murray, L.C. Seavers, R.L. Van Montfort, J. Med. Chem. 49, 1346 (2006)

    Article  CAS  Google Scholar 

  4. P.S. Watson, B. Jiang, B. Scott, Org. Lett. 2, 3679 (2000)

    Article  CAS  Google Scholar 

  5. M. Rudrapal, B. De, Int. Res. J. Pure Appl. Chem. 3, 232 (2013)

    Article  Google Scholar 

  6. D. O’Hagan, Nat. Prod. Rep. 17, 435 (2000)

    Article  Google Scholar 

  7. Y. Zhou, V.E. Gregor, B.K. Ayida, G.C. Winters, Z. Sun, D. Murphy, G. Haley, D. Bailey, J.M. Froelich, S. Fish, Bioorg. Med. Chem. Lett. 17, 1206 (2007)

    Article  CAS  Google Scholar 

  8. S. Petit, J. Nallet, M. Guillard, J. Dreux, R. Chermat, M. Poncelet, C. Bulach, P. Simon, C. Fontaine, M. Barthelmebs, Eur. J. Med. Chem. 26, 19 (1991)

    Article  CAS  Google Scholar 

  9. R. Gitto, L. De Luca, S. Ferro, F. Occhiuto, S. Samperi, G. De Sarro, E. Russo, L. Ciranna, L. Costa, A. Chimirri, Chem. Med. Chem. 3, 1539 (2008)

    Article  CAS  Google Scholar 

  10. B. Ho, A.M. Crider, J.P. Stables, Eur. J. Med. Chem. 36, 265 (2001)

    Article  CAS  Google Scholar 

  11. I. Borza, G. Domany, Curr. Top. Med. Chem. 6, 687 (2006)

    Article  CAS  Google Scholar 

  12. L. Mony, J.N. Kew, M.J. Gunthorpe, P. Paoletti, Br. J. Pharmacol. 157, 1301 (2009)

    Article  CAS  Google Scholar 

  13. M. Misra, S.K. Pandey, V.P. Pandey, J. Pandey, R. Tripathi, R.P. Tripathi, Bioorg. Med. Chem. 17, 625 (2009)

    Article  CAS  Google Scholar 

  14. S.L. Gwaltney, S.J. O’Connor, L.T. Nelson, G.M. Sullivan, H. Imade, W. Wang, L. Hasvold, Q. Li, J. Cohen, W.Z. Gu, Bioorg. Med. Chem. Lett. 13, 1359 (2003)

    Article  CAS  Google Scholar 

  15. N.H. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, J. Aboonajmi, S.S. Sajadikhah, J. Chin. Chem. Soc. 60, 355 (2013)

    Article  CAS  Google Scholar 

  16. P.E. Goss, M.A. Baker, J.P. Carver, J.W. Dennis, Clin. Cancer Res. 1, 935 (1995)

    CAS  Google Scholar 

  17. P. Chand, P.L. Kotian, A. Dehghani, Y. El Kattan, T.H. Lin, T.L. Hutchison, Y.S. Babu, S. Bantia, A.J. Elliott, J.A. Montgomery, J. Med. Chem. 44, 4379 (2001)

    Article  CAS  Google Scholar 

  18. J.L. Treadway, P. Mendys, D.J. Hoover, Expert Opin. Investig. Drugs 10, 439 (2001)

    CAS  Google Scholar 

  19. G. Karlsson, T.D. Butters, R.A. Dwek, F.M. Platt, J. Biol. Chem. 268, 570 (1993)

    CAS  Google Scholar 

  20. P.A. Clarke, A.V. Zaytsev, A.C. Whitwood, Synthesis 2008, 3530 (2008)

    Article  Google Scholar 

  21. P.A. Clarke, A.V. Zaytzev, A.C. Whitwood, Tetrahedron Lett. 48, 5209 (2007)

    Article  CAS  Google Scholar 

  22. A.T. Khan, T. Parvin, L.H. Choudhury, J. Org. Chem. 73, 8398 (2008)

    Article  CAS  Google Scholar 

  23. A.T. Khan, M. Lal, M.M. Khan, Tetrahedron Lett. 51, 4419 (2010)

    Article  CAS  Google Scholar 

  24. A.T. Khan, M.M. Khan, K.K. Bannuru, Tetrahedron 66, 7762 (2010)

    Article  CAS  Google Scholar 

  25. H.J. Wang, L.P. Mo, Z.H. Zhang, ACS. Comb. Sci. 13, 181 (2010)

    Article  Google Scholar 

  26. S. Mishra, R. Ghosh, Tetrahedron Lett. 52, 2857 (2011)

    Article  CAS  Google Scholar 

  27. R. Ramachandran, S. Jayanthi, Y.T. Jeong, Tetrahedron 68, 363 (2012)

    Article  CAS  Google Scholar 

  28. G. Brahmachari, S. Das, Tetrahedron Lett. 53, 1479 (2012)

    Article  CAS  Google Scholar 

  29. C. Mukhopadhyay, S. Rana, R.J. Butcher, A.M. Schmiedekamp, Tetrahedron Lett. 52, 5835 (2011)

    Article  CAS  Google Scholar 

  30. S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, A.C. Willis, Chin. Chem. Lett. 23, 569 (2012)

    Article  CAS  Google Scholar 

  31. M. Lashkari, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, S.S. Sajadikhah, R. Doostmohamadi, Synth. Commun. 43, 635 (2013)

    Article  CAS  Google Scholar 

  32. Y.N. Bubnov, E.V. Klimkina, A.V. Ignatenko, I.D. Gridnev, Tetrahedron Lett. 37, 1317 (1996)

    Article  CAS  Google Scholar 

  33. Y. Genisson, C. Marazano, M. Mehmandoust, D. Gnecco, B.C. Das, Synlett 1992, 431 (1992)

    Article  Google Scholar 

  34. L. Overman, C. Flann, T. Malone, Org. Synth. 68, 188 (1990)

    Article  CAS  Google Scholar 

  35. C. Agami, S. Comesse, C. Kadouri-Puchot, Tetrahedron Lett. 41, 6059 (2000)

    Article  CAS  Google Scholar 

  36. C. Agami, S. Comesse, C. Kadouri-Puchot, J. Org. Chem. 67, 1496 (2002)

    Article  CAS  Google Scholar 

  37. G.W. Daub, D.A. Heerding, L.E. Overman, Tetrahedron 44, 3919 (1988)

    Article  CAS  Google Scholar 

  38. H. Huang, T.F. Spande, J.S. Panek, J. Am. Chem. Soc. 125, 626 (2003)

    Article  CAS  Google Scholar 

  39. Y. Yamakado, M. Ishiguro, N. Ikeda, H. Yamamoto, J. Am. Chem. Soc. 103, 5568 (1981)

    Article  CAS  Google Scholar 

  40. T.K. Yang, T.F. Teng, J.H. Lin, Y.Y. Lay, Tetrahedron Lett. 35, 3581 (1994)

    Article  CAS  Google Scholar 

  41. X.F. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc. 125, 4716 (2003)

    Article  CAS  Google Scholar 

  42. Y. Chai, S.P. Hong, H.A. Lindsay, C. McFarland, M.C. McIntosh, Tetrahedron 58, 2905 (2002)

    Article  CAS  Google Scholar 

  43. J. Ahman, T. Jarevång, P. Somfai, J. Org. Chem. 61, 8148 (1996)

    Article  Google Scholar 

  44. J. Ahman, P. Somfai, J. Am. Chem. Soc. 116, 9781 (1994)

    Article  Google Scholar 

  45. J.C. Anderson, C.A. Roberts, Tetrahedron Lett. 39, 159 (1998)

    Article  CAS  Google Scholar 

  46. T. Nakai, K. Tomooka, Pure Appl. Chem. 69, 595 (1997)

    Article  CAS  Google Scholar 

  47. A. Sambyal, R. Bamezai, T. Razdan, V.K. Gupta, J. Chem. Crystallogr. 41, 868 (2011)

    Article  CAS  Google Scholar 

  48. P.D. Bailey, G.R. Brown, P. Korber, A. Reed, R.D. Wilson, Tetrahedron Asymmetry 2, 1263 (1991)

    Article  CAS  Google Scholar 

  49. P.D. Bailey, P.D. Smith, F. Pederson, W. Clegg, G.M. Rosair, S.J. Teat, Tetrahedron Lett. 43, 1067 (2002)

    Article  CAS  Google Scholar 

  50. T. Hamada, H. Sato, M. Hikota, O. Yonemitsu, Tetrahedron Lett. 30, 6405 (1989)

    Article  CAS  Google Scholar 

  51. T. Hamada, T. Zenkoh, H. Sato, O. Yonemitsu, Tetrahedron Lett. 32, 1649 (1991)

    Article  CAS  Google Scholar 

  52. S.C. Schürer, S. Blechert, Tetrahedron Lett. 40, 1877–1880 (1999)

    Article  Google Scholar 

  53. G. Arce, G. Carrau, A. Bellomo, D. Gonzalez, World J. Chem. Edu. 3, 27 (2015)

    Article  CAS  Google Scholar 

  54. S. Chandrasekhar, K. Gopalaiah, Tetrahedron Lett. 43, 2455 (2002)

    Article  CAS  Google Scholar 

  55. C.K. Khatri, D.S. Rekunge, G.U. Chaturbhuj, New J. Chem. 40, 10412 (2016)

    Article  CAS  Google Scholar 

  56. D.S. Rekunge, K.S. Indalkar, G.U. Chaturbhuj, Tetrahedron Lett. 57, 5815 (2016)

    Article  CAS  Google Scholar 

  57. K.S. Indalkar, C.K. Khatri, G.U. Chaturbhuj, J. Chem. Sci. 129, 141 (2017)

    Article  CAS  Google Scholar 

  58. K.S. Indalkar, C.K. Khatri, G.U. Chaturbhuj, J. Chem. Sci. 129, 415 (2017)

    Article  CAS  Google Scholar 

  59. K.S. Indalkar, C.K. Khatri, G.U. Chaturbhuj, Tetrahedron Lett. 58, 2144 (2017)

    Article  CAS  Google Scholar 

  60. C.K. Khatri, A.S. Mali, G.U. Chaturbhuj, Monatsh. Chem. 148, 1463 (2017)

    Article  CAS  Google Scholar 

  61. C.K. Khatri, M.S. Patil, G.U. Chaturbhuj, J. Iran. Chem. Soc. 8, 1683 (2017)

    Article  Google Scholar 

  62. C.K. Khatri, S.M. Potadar, G.U. Chaturbhuj, Tetrahedron Lett. 58, 1778 (2017)

    Article  CAS  Google Scholar 

  63. C.K. Khatri, V.B. Satalkar, G.U. Chaturbhuj, Tetrahedron Lett. 58, 694 (2017)

    Article  CAS  Google Scholar 

  64. M.S. Patil, A.V. Palav, C.K. Khatri, G.U. Chaturbhuj, Tetrahedron Lett. 58, 2859 (2017)

    Article  CAS  Google Scholar 

  65. D.S. Rekunge, C.K. Khatri, G.U. Chaturbhuj, Tetrahedron Lett. 58, 1240 (2017)

    Article  CAS  Google Scholar 

  66. C.K. Khatri, G.U. Chaturbhuj, J. Iran. Chem. Soc. 14, 2513 (2017)

    Article  CAS  Google Scholar 

  67. D.S. Rekunge, C.K. Khatri, G.U. Chaturbhuj, Monatsh. Chem. 148, 2019 (2017)

    Google Scholar 

  68. D.S. Rekunge, C.K. Khatri, G.U. Chaturbhuj, Tetrahedron Lett. 58, 4304 (2017)

    Article  CAS  Google Scholar 

  69. M.S. Patil, C. Mudaliar, G.U. Chaturbhuj, Tetrahedron Lett. 58, 3256–3261 (2017)

    Article  CAS  Google Scholar 

  70. K.S. Indalkar, M.S. Patil, G.U. Chaturbhuj, Tetrahedron Lett. 58, 4496 (2017)

    Article  CAS  Google Scholar 

  71. M.S. Patil, C.K. Khatri, G.U. Chaturbhuj, Monatsh. Chem. (2018). https://doi.org/10.1007/s00706-018-2169-z

    Google Scholar 

  72. R.L. Siqueira, I.V.P. Yoshida, L.C. Pardini, M.A. Schiavon, Mater. Res. 10, 147 (2007)

    Article  CAS  Google Scholar 

  73. J.S. Yeo, T.H. Park, S.H. Yoon, M.H. Seo, J. Miyawaki, I. Mochida, Int. J. Electrochem. Sci. 8, 1308 (2013)

    CAS  Google Scholar 

  74. A. Khalafi-Nezhad, H. Ollah Foroughi, M.M. Doroodmand, F. Panahi, J. Mater. Chem. 21, 12842 (2011)

    Article  CAS  Google Scholar 

  75. H.J. Jung, Y. Sohn, H. G., H.S. Hyun, and W.G. Shin, 2015. Powder Technol. 269, 548 (2015)

    Article  CAS  Google Scholar 

  76. C. Mandilas, E. Daskalos, G. Karagiannakis, A.G. Konstandopoulos, Mater. Sci. Eng., B 178, 22 (2013)

    Article  CAS  Google Scholar 

  77. J. Shorrock, J. Clark, K. Wilson, J. Chisem, Org. Process Res. Dev. 5, 249 (2001)

    Article  CAS  Google Scholar 

  78. V.P. Jejurkar, C.K. Khatri, G.U. Chaturbhuj, S. Saha, ChemistrySelect 2(35), 11693–11696 (2017)

    Article  CAS  Google Scholar 

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Acknowledgements

Authors are grateful to University Grant Commission, India, for their financial support.

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Authors and Affiliations

  1. Department of Pharmaceutical Sciences and Technology, Institute of Chemical Technology, Mumbai, 400019, India

    Anil S. Mali & Ganesh U. Chaturbhuj

  2. V. G. Vaze College of Arts, Science, and Commerce, Mumbai, 400081, India

    Chinmay S. Potnis

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  1. Anil S. Mali
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  2. Chinmay S. Potnis
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  3. Ganesh U. Chaturbhuj
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Correspondence to Ganesh U. Chaturbhuj.

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Mali, A.S., Potnis, C.S. & Chaturbhuj, G.U. Aluminized polyborate: a novel catalyst for the multicomponent solvent-free synthesis of alkyl 1,2,6-trisubstituted-4-[(hetero)arylamino]-1,2,5,6-tetrahydropyridine-3-carboxylates. J IRAN CHEM SOC 15, 1399–1409 (2018). https://doi.org/10.1007/s13738-018-1340-0

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