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Synthesis of a polymer-capped palladium nanoparticles and its application as a reusable catalyst in oxidative coupling reaction of α-hydroxyketones and 1,2-diamines for preparation of pyrazines and quinoxalines

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Abstract

A novel method for the synthesis of pyrazines and quinoxalines has been developed using α-hydroxyketones and 1,2-diamines in the presence of cross-linked poly(4-vinylpyridine)-stabilized Pd(0) nanoparticles, [P4-VP]-PdNPs. The catalyst was easily prepared and characterized using various techniques such as FT-IR and UV–Vis spectroscopy, AAS, TEM, FESEM, EDX analysis and XRD. The results confirm a good dispersion of palladium nanoparticles on the polymer support. The catalyst displayed good catalytic activity when applied to the synthesis of quinoxalines via condensation of α-hydroxyketones with 1,2-diamines. A few pyrazine derivatives and various quinoxalines are prepared via coupling reaction of α-hydroxyketones and 1,2-diamines in high–excellent yields (81–99%) with short reaction times. The quinoxalines products were characterized by FT-IR, 1H and 13C NMR spectroscopy, and the physical properties were compared to the literature values of known compounds. The advantages of the present method over conventional classical methods are rapid and very simple work-up, and the catalyst is reusable many times without a significant loss in its activity.

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References

  1. D. Sherman, J. Kawakami, H.Y. He, F. Dhun, R. Rios, H. Liu, W. Pan, Y.J. Xu, S.P. Hong, M. Arbour, M. Labelle, M.A.J. Duncton, Tetrahedron Lett. 48, 8943 (2007)

    Article  CAS  Google Scholar 

  2. J.A. Pereira, A.M. Pessoa, M.N.D.S. Cordeiro, R. Fernandes, C. Prudencio, J.P. Noronha, M. Vierira, Euro. J. Med. Chem. 97, 664 (2015)

    Article  CAS  Google Scholar 

  3. L.M. Wilhelmsson, N. Kingi, J. Bergman, J. Med. Chem. 51, 7744 (2008)

    Article  CAS  Google Scholar 

  4. Q. Weng, D. Wang, P. Guo, L. Fang, Y. Hu, Q. He, B. Yang, Euro. J. Pharmacol. 581, 262 (2008)

    Article  CAS  Google Scholar 

  5. Y. Xu, F. Wu, Z. Yao, M. Zhang, S. Jiang, Molecules 16, 6894 (2011)

    Article  CAS  Google Scholar 

  6. C.H. Sridevi, K. Balaji, A. Naidu, R. Sudhakaran, Euro. J. Chem. 7, 234 (2010)

    CAS  Google Scholar 

  7. A. Dell, D.H. William, H.R. Morris, G.A. Smith, J. Feeney, G.C.K. Roberts, J. Am. Chem. Soc. 97, 2497 (1975)

    Article  CAS  Google Scholar 

  8. S.A. Raw, C.D. Wilfred, R.J.K. Taylor, Chem. Commun. 18, 2286 (2003)

    Article  Google Scholar 

  9. A. Kumar, S. Kumar, A. Saxena, A. De, S. Mozumdar, Catal. Commun. 9(5), 778 (2008)

    Article  CAS  Google Scholar 

  10. J.Y. Jaung, Dyes Pigments 71, 45 (2006)

    Article  Google Scholar 

  11. S. Dailey, W.J. Feast, R.J. Peace, I.C. Sage, S. Till, E.L. Wood, J. Mater. Chem. 11, 2238 (2001)

    Article  CAS  Google Scholar 

  12. T.R.J. Thomas, K.M. Velusamy, J.T. Lin, C.H. Chuen, Y.T. Tao, Chem. Mater. 17, 1860 (2005)

    Article  CAS  Google Scholar 

  13. M.J. Crossley, L.A. Johnston, Chem. Commun. 10, 1122 (2002)

    Article  Google Scholar 

  14. K. Aghapoor, F. Mohsenzadeh, M. Mohebi Morad, H.R. Darabi, Transit. C. R. Chimie 15, 764 (2012)

    Article  CAS  Google Scholar 

  15. C. Srinivas, C.N.S.S.P. Kumar, V.J. Rao, S. Palaniappan, J. Mol. Catal. A Chem. 265, 227 (2007)

    Article  CAS  Google Scholar 

  16. B.A.D.S. Neto, A.S. Lopes, M. Wust, V.E.U. Costa, G. Ebeling, J. Dupont, J. Tetrahedron Lett. 46, 6843 (2005)

    Article  Google Scholar 

  17. H.R. Darabi, F. Tahoori, K. Aghapoor, F. Taala, F. Mohsenzadeh, J. Braz. Chem. Soc. 19, 1646 (2008)

    Article  CAS  Google Scholar 

  18. J.J. Cai, J.P. Zou, X.Q. Pan, W. Zhang, Tetrahedron Lett. 49, 7386 (2008)

    Article  CAS  Google Scholar 

  19. M.R. Islami, Z. Hassani, Arkivoc xv, 280 (2008)

    Google Scholar 

  20. D.J. Brown, Quinoxalines: Supplement II, The Chemistry of Heterocyclic Compounds (Wiley, New Jersey, 2004)

    Book  Google Scholar 

  21. S.Y. Kim, K.H. Park, Y.K. Chung, Chem. Commun. 10, 1321 (2005)

    Article  Google Scholar 

  22. S. Antoniotti, E. Donach, Tetrahedron Lett. 43, 3971 (2002)

    Article  CAS  Google Scholar 

  23. D. Aparicio, O.A. Attanasi, P. Filippone, R. Ignacio, S. Lillini, F. Mantellini, F. Palacios, J.M. Santos, J. Org. Chem. 71, 5897 (2006)

    Article  CAS  Google Scholar 

  24. Z. Wu, N.J. Ede, Tetrahedron Lett. 42, 8115 (2001)

    Article  CAS  Google Scholar 

  25. S.K. Singh, P. Gupta, S. Duggineni, B. Kundu, Synlett 2003, 2147 (2003)

    Google Scholar 

  26. R.S. Robinson, R.J.K. Taylor, Synlett 2005, 1003 (2005)

    Article  Google Scholar 

  27. M. Beller, H. Fischer, K. Kuhlein, C.P. Reisinger, W.A. Hermann, J. Organomet. Chem. 520, 257 (1996)

    Article  CAS  Google Scholar 

  28. C.P. Mehnert, J.Y. Ying, Chem. Commun. 2215 (1997)

  29. D.C. Sherrington, P. Hodge, Synthesis and Separations Using Functional Polymers (Wiley, New York, 1988)

    Google Scholar 

  30. A. Akelah, D.C. Sherrington, Polymer 24, 1369 (1984)

    Article  Google Scholar 

  31. S.V. Ley, I.R. Baxendale, R.N. Bream, P.S. Jackson, A.G. Leach, D.A. Longbottom, M. Nesi, J.S. Scott, R.I. Storer, S.J. Taylor, J. Chem. Soc. Perkin Trans. 1, 3815 (2000)

    Article  Google Scholar 

  32. M.A. Karimi Zarchi, R. Nabaei, S. Barani, J. Appl. Polym. Sci. 123, 788 (2012)

    Article  Google Scholar 

  33. M.A. Karimi Zarchi, R. Nabaei, J. Appl. Polym. Sci. 124, 2362 (2012)

    Article  Google Scholar 

  34. M.A. Karimi Zarchi, S. Barani, Chinese. J. Polym. Sci. 31, 1002 (2013)

    Google Scholar 

  35. M.A. Karimi Zarchi, F. Nazem, J. Appl. Polym. Sci. 123, 1977 (2012)

    Article  Google Scholar 

  36. M.A. Karimi Zarchi, F. Nazem, J. Iran. Chem. Soc. 11, 91 (2014)

    Article  CAS  Google Scholar 

  37. M.A. Karimi Zarchi, F. Nazem, J. Iran. Chem. Soc. 11, 1731 (2014)

    Article  CAS  Google Scholar 

  38. M.A. Karimi Zarchi, Z. Escandari, J. Appl. Polym. Sci. 121, 1916 (2011)

    Article  Google Scholar 

  39. M.A. Karimi Zarchi, N. Ebrahimi, J. Appl. Polym. Sci. 121, 2621 (2011)

    Article  Google Scholar 

  40. M.A. Karimi Zarchi, N. Ebrahimi, J. Appl. Polym. Sci. 124, 2807 (2012)

    Article  Google Scholar 

  41. M.A. Karimi Zarchi, N. Ebrahimi, Iran. Polym. J. 21, 591 (2012)

    Article  CAS  Google Scholar 

  42. M.A. Karimi Zarchi, N. Ebrahimi, J. Appl. Polym. Sci. 125, 2163 (2012)

    Article  Google Scholar 

  43. M.A. Karimi Zarchi, N. Ebrahimi, Phosphorous Sulfur Silicon Relat. Elem. 187, 1226 (2012)

    Article  Google Scholar 

  44. M.A. Karimi Zarchi, R. Banihashemi, Phosphorus Sulfur Silicon Relat. Elem. 189, 1378 (2014)

    Article  Google Scholar 

  45. M.A. Karimi Zarchi, A. Tarabsaz, Phosphorous Sulfur Silicon Relat. Elem. 190, 550 (2015)

    Article  Google Scholar 

  46. M.A. Karimi Zarchi, A. Tarabsaz, J. Polym. Res. 20, 208 (2013)

    Article  Google Scholar 

  47. M.A. Karimi Zarchi, A. Tarabsaz, Chin. J. Polym. Sci. 31, 1660 (2013)

    Article  Google Scholar 

  48. M.A. Karimi Zarchi, A. Tabatabaei Bafghi, J. Sulfur Chem. 36, 403 (2015)

    Article  CAS  Google Scholar 

  49. M.A. Karimi Zarchi, S.Z. Mousavi, J. Polym. Sci. 21, 330 (2014)

    Google Scholar 

  50. M.A. Karimi Zarchi, R. Banihashemi, J. Sulfur Chem. 37, 282 (2016)

    Article  CAS  Google Scholar 

  51. L.D. Rampino, F.F. Nord, J. Am. Chem. Soc. 63, 2745 (1941)

    Article  CAS  Google Scholar 

  52. Y. Li, X.M. Hong, D.M. Collard, M.A. El-Sayed, Org. Lett. 2, 2385 (2000)

    Article  CAS  Google Scholar 

  53. D.D.L. Martins, H.M. Alvarez, L.C.S. Aguiar, Tetrahedron Lett. 51, 6814 (2010)

    Article  CAS  Google Scholar 

  54. Y. Li, E. Boone, M.A. El-Sayed, Langmuir 18, 4921 (2002)

    Article  CAS  Google Scholar 

  55. K.A. Guy, J.R. Shapley, Organometallics 28, 4020 (2009)

    Article  CAS  Google Scholar 

  56. R. Narayanan, M.A. El-Sayed, J. Am. Chem. Soc. 125, 8340 (2003)

    Article  CAS  Google Scholar 

  57. J.L. Lan, C.C. Wan, Y.Y. Wang, J. Electrochem. Soc. 155, K77 (2008)

    Article  CAS  Google Scholar 

  58. P. Li, L. Wang, H. Li, Tetrahedron 61, 8633 (2005)

    Article  CAS  Google Scholar 

  59. A. Gniewek, A.M. Trzeciak, J.J. Ziolkowski, L. Kepinski, J. Wrzyszcz, W. Tylus, J. Catal. 229, 332 (2005)

    Article  CAS  Google Scholar 

  60. D.D.L. Martins, H.M. Alvarez, L.C.S. Aguiar, O.A.C. Antunes, Appl. Catal. A Gener. 408, 47 (2011)

    Article  CAS  Google Scholar 

  61. A. Drelinkiewicz, M. Hasik, J. Mol. Catal. A Chem. 177, 149 (2001)

    Article  CAS  Google Scholar 

  62. A.L.F.D. Souza, L.C.D. Silva, B.L. Oliveira, O.A.C. Antunes, Tetrahedron Lett. 49, 3895 (2008)

    Article  Google Scholar 

  63. K.A. Guy, H. Xu, J.C. Yang, C.J. Werth, J.R. Shapley, J. Phys. Chem. C 113, 8177 (2009)

    Article  CAS  Google Scholar 

  64. F. Durap, O. Metin, M. Aydemir, S. Ozkar, Appl. Organomet. Chem. 23, 498 (2009)

    Article  CAS  Google Scholar 

  65. C. Evangelisti, N. Panziera, A.D. Alessio, L. Bertinetti, M. Botavina, J. Catal. 272, 246 (2010)

    Article  CAS  Google Scholar 

  66. B. Tamami, H. Allahyari, S. Ghasemi, F. Farjadian, J. Organomet. Chem. 696, 594 (2011)

    Article  Google Scholar 

  67. J. Zou, K.S. Iyer, S.G. Stewart, C.L. Raston, New J. Chem. 35, 854 (2011)

    Article  CAS  Google Scholar 

  68. D. Shah, H. Kaur, Curr. Catal. 3, 39 (2014)

    Article  CAS  Google Scholar 

  69. Y. Zhao, J.A. Baeza, N.K. Rao, L. Calvo, M.A. Gilarranz, Y.D. Li, L. Lefferts, J. Catal. 318, 162 (2014)

    Article  CAS  Google Scholar 

  70. M. Abdollahi-Alibeik, E. Heidari-Torkabad, C. R. Chim. 15, 517 (2012)

    Article  CAS  Google Scholar 

  71. K. Niknam, D. Saberi, M. Mohagheghnejad, Molecules 14, 1915 (2009)

    Article  CAS  Google Scholar 

  72. H.A. Oskooie, M.M. Heravi, K. Bakhtiari, M.H. Tehrani, Monatsh. Chem. 138, 875 (2007)

    Article  CAS  Google Scholar 

  73. W.X. Guo, H.L. Jin, J.X. Chen, F. Chen, J.C. Ding, H.Y. Wu, J. Braz. Chem. Soc. 20, 1674 (2009)

    Article  CAS  Google Scholar 

  74. M.M. Heravi, M.H. Tehrani, K. Bakhtiari, H.A. Oskooie, Catal. Commun. 8, 1341 (2007)

    Article  CAS  Google Scholar 

  75. A.L. Santana, L.K. Noda, A.N.T. Pires, J.R. Bertoline, Polym. Test 23, 839 (2004)

    Article  CAS  Google Scholar 

  76. A. Drelinkiewicz, M. Hasik, S. Quillard, C. Paluszkiewicz, J. Mol. Struct. 511–512, 205 (1999)

    Article  Google Scholar 

  77. F. Pan, T.M. Chen, J.J. Cao, J.P. Zou, W. Zhang, Tetrahedron Lett. 53, 2508 (2012)

    Article  CAS  Google Scholar 

  78. L.Y. Fan, L. Wei, W.J. Hua, X.X. Li, Chin. Chem. Lett. 25, 1203 (2014)

    Article  CAS  Google Scholar 

  79. T. Bhattacharya, T.K. Sarma, S. Samanta, Catal. Sci. Technol. 2, 2216 (2012)

    Article  CAS  Google Scholar 

  80. N. Shah, E. Gravel, D.V. Jawale, E. Doris, I.N.N. Namboothiri, Chem. Cat. Chem. 6, 719 (2014)

    Google Scholar 

  81. T. Hara, Y. Takami, N. Ichikuni, S. Shimazu, Chem. Lett. 41, 488 (2012)

    Article  CAS  Google Scholar 

  82. S. Sithambaram, Y. Ding, W. Li, X. Shen, F. Gaenzler, S.L. Suib, Green Chem. 10, 1029 (2008)

    Article  CAS  Google Scholar 

  83. K.T.V. Rao, P.S.S. Prasad, N. Lingaiah, J. Mol. Catal. A Chem. 312, 65 (2009)

    Article  Google Scholar 

  84. A. Kamal, K.S. Babu, S. Faazil, S.M. Ali Hussaini, A.B. Shaik, RSC Adv. 4, 46369 (2014)

    Article  CAS  Google Scholar 

  85. W. Song, P. Liu, M. Lei, H. You, X. Chen, H. Chen, L. Ma, L. Hu, Synth. Commun. 42, 236 (2012)

    Article  CAS  Google Scholar 

  86. A. Kamal, K.S. Babu, S.M. Ali Hussaini, R. Mahesh, A. Alarifi, Tetrahedron Lett. 56, 2803 (2015)

    Article  CAS  Google Scholar 

  87. V. Jeena, R.S. Robinson, Tetrahedron Lett. 55, 642 (2014)

    Article  CAS  Google Scholar 

  88. C. Xie, Z. Zhang, B. Yang, G. Song, H. Gao, L. Wen, C. Ma, Tetrahedron 71, 1831 (2015)

    Article  CAS  Google Scholar 

  89. R.S. Robinson, R.J.K. Taylor, Synlett 6, 1003 (2005)

    Google Scholar 

  90. N.J. Turro, Tetrahedron 43, 1589 (1987)

    Article  CAS  Google Scholar 

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  1. Department of Chemistry, College of Science, Yazd University, P. O. Box 89195-741, 8915813149, Yazd, Iran

    Mohammad Ali Karimi Zarchi & Seyed Shahab Addin Darbandizadeh Mohammad Abadi

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  1. Mohammad Ali Karimi Zarchi
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  2. Seyed Shahab Addin Darbandizadeh Mohammad Abadi
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Correspondence to Mohammad Ali Karimi Zarchi.

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Zarchi, M.A.K., Abadi, S.S.A.D.M. Synthesis of a polymer-capped palladium nanoparticles and its application as a reusable catalyst in oxidative coupling reaction of α-hydroxyketones and 1,2-diamines for preparation of pyrazines and quinoxalines. J IRAN CHEM SOC 15, 915–929 (2018). https://doi.org/10.1007/s13738-018-1290-6

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