A novel one-pot and rapid synthesis of polyfunctionalized benzo[a]pyrimido[5’,4’:5,6] pyrido[2,3-c]phenazine derivatives under microwave irradiation

  A one-pot, environmentally friendly, and efficient protocol for the synthesis of novel polyfunctionalized benzo[aaa]pyrimido[5',4':5,6]pyrido[2,3-ccc]phenazine derivatives has been reported by a one-pot, four-component sequential reaction between 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamines, benzaldehydes, and 6-amino-1,3-dimethyluracil in the presence of ppp-TSA as a nontoxic, inexpensive, ecofriendly, and efficacious solid acid catalyst. Two C-C bonds, two C=N bonds, and one C-N bond, as well as two new rings, were formed in this reaction. Through this procedure, compounds with substantial biological and pharmaceutical properties are generated in a single operation. Factors such as high yields, less reaction time, operational simplicity, and lack of any dangerous reagents/solvents have made this process a green one.

___

  • Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996 , 96 , 195-206.
  • Yazdani-Elah-Abadi, A.; Mohebat, R.; Maghsoodlou, M. T. RSC Adv. 2016 , 6 , 84326-84333.
  • Polshettiwar, V.; Varma, R. S. Acc. Chem. Res. 2008 , 41 , 629-639.
  • Satasia, S. P.; Kalaria, P. N.; Raval, D. K. Org. Biomol. Chem. 2014 , 12 , 1751-1758.
  • Blaney, J. M.; Hansch, C.; Silipo, C.; Vittoria, A. Chem. Rev. 1984 , 84 , 333-407.
  • Castle, R.; Phillips, S.; Katritzky, A.; Rees, C.; Boulton, A.; McKillop, A. Comprehensive Heterocyclic Chemistry, Vol. 3 ; Pergamon Press: Oxford, UK, 1984.
  • Gut, J. Adv. Heterocycl. Chem. 1963 , 1 , 189-251.
  • Ribble, W.; Hill, W. E.; Ochsner, U. A.; Jarvis, T. C.; Guiles, J. W.; Janjic, N.; Bullard, J. M. Antimicrob. Agents Chemother. 2010 , 54 , 4648-4657.
  • Duan, S.; Place, D.; Perfect, H. H.; Ide, N. D.; Maloney, M.; Sutherland, K.; Price Wiglesworth, K. E.; Wang, K.; Olivier, M.; Kong, F. Org. Process Res. Dev. 2016 , 20 , 1191-1202.
  • VanderWel, S. N.; Harvey, P. J.; McNamara, D. J.; Repine, J. T.; Keller, P. R.; Quin, J.; Booth, R. J.; Elliott, W. L.; Dobrusin, E. M.; Fry, D. W. J. Med. Chem. 2005 , 48 , 2371-2387.
  • Singh, G.; Singh, G.; Yadav, A. K.; Mishra, A. Indian J. Chem. 2002 , 41B , 430-432.
  • Quintela, J.; Peinador, C.; Botana, L.; Estévez, M.; Riguera, R. Bioorgan. Med. Chem. 1997 , 5 , 1543-1553.
  • Bazgir, A.; Khanaposhtani, M. M.; Soorki, A. A. Bioorg. Med. Chem. Lett. 2008 , 18 , 5800-5803.
  • El-Gazzar, A. R. B.; Hafez, H. N. Bioorg. Med. Chem. Lett. 2009 , 19 , 3392-3397.
  • Laursen, J. B.; Nielsen, J. Chem. Rev. 2004 , 104 , 1663-1686.
  • Hafez, H.; Hegab, M.; Ahmed-Farag, I.; El-Gazzar, A. Bioorg. Med. Chem. Lett. 2008 , 18 , 4538-4543.
  • Cimmino, A.; Evidente, A.; Mathieu, V.; Andolfi, A.; Lefranc, F.; Kornienko, A.; Kiss, R. Nat. Prod. Rep. 2012 , 29 , 487-501.
  • Ligon, J. M.; Hill, D. S.; Hammer, P. E.; Torkewitz, N. R.; Hofmann, D.; Kempf, H. J.; Pée, K. H. V. Pest Manag. Sci. 2000 , 56 , 688-695.
  • Makgatho, M. E.; Anderson, R.; O’Sullivan, J. F.; Egan, T. J.; Freese, J. A.; Cornelius, N.; van Rensburg, C. E. Drug Dev. Res. 2000 , 50 , 195-202.
  • Nishanth Kumar, S.; Nisha, G.; Sudaresan, A.; Venugopal, V.; Sree Kumar, M.; Lankalapalli, R. S.; Dileep Kumar, B. Med. Mycol. 2014 , 52 , 482-490.
  • Wang, J.; Zhi, X.; Yu, X.; Xu, H. J. Agric. Food. Chem. 2013 , 61 , 6336-6343.
  • Mohebat, R.; Yazdani Elah Abadi, A.; Maghsoodlou, M. T.; Mohammadi, M. Res. Chem. Intermed. 2016 , 42 , 5915-5926.
  • Yazdani-Elah-Abadi, A.; Maghsoodlou, M. T.; Mohebat, R.; Heydari; R. Chin. Chem. Lett. 2017 , 28 , 446-452.
  • Mohebat, R.; Yazdani-Elah-Abadi, A. Chin. Chem. Lett. 2017 , 28 , 1340-1344.
  • Mohebat, R.; Yazdani-Elah-Abadi, A.; Maghsoodlou, M. T.; Hazeri, N. Chin. Chem. Lett. 2017 , 28 , 943-948.
  • Ji, S. J.; Ni, S. N.; Yang, F.; Shi, J. W.; Dou, G. L.; Li, X. Y.; Wang, X. S.; Shi, D. Q. J. Heterocyclic Chem. 2008 , 45 , 693-702.