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A Novel Route to New Bis(benzopyrano) Fused Dihydropyridines Using Dry Media

  • Published : 2004.01.20
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Abstract

A new and efficient synthesis of the novel bioactive bis(benzopyrano) fused dihydropyridines is described. The conventionally developed route is a two step multicomponent condensation reaction. This is latter modified by a one pot microwave (MW) assisted reaction using inorganic solid support via the arylidene derivative intermediate. With this environmentally benign approach, the reaction time is brought down from hours to minutes along with a yield enhancement. Furthermore, the role of different solid supports is studied and it is concluded that the acidic alumina is the best solid support for the present investigation.

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References

  1. Sunkel, C. E.; de Casa-Juana, M. F.; Santos, L.; Gomez, M. M.;Villarroya, M.; Gonzalez-Morales, M. A.; Priego, J. G.; Ortega,M. P. J. Med. Chem. 1990, 33, 3205. https://doi.org/10.1021/jm00174a017
  2. Rovnyak, G. C.; Kimball, S. D.; Beyer, B.; Cucinotta, G.; DiMarco,J. D.; Gougoutas, J.; Hedberg, A.; Malley, M.; McCarthy, J. P.;Zhang, R.; Moreland, S. J. Med. Chem. 1995, 38, 119. https://doi.org/10.1021/jm00001a017
  3. Archibald, J. L.; Bradley, G.; Opalko, A.; Ward, T. J.; White, J. C.;Ennis, C.; Shapperson, N. B. J. Med. Chem. 1990, 33, 646. https://doi.org/10.1021/jm00164a028
  4. Hutton, R. F.; Westheimer, F. H. Tetrahedron 1958, 3, 73. https://doi.org/10.1016/S0040-4020(01)82613-2
  5. Paraskar, S. R.; Ladwa, P. H. Indian J. Chem. 1983, 22B, 829.
  6. Witte, E. C.; Thiel, M.; Stach, K.; Schmidt, F. H.; Stork, H. Ger. Offen. 2,034,306; Chem. Abstr. 1972, 76, 99512.
  7. Massarani, E.; Nardi, D.; Barzaghi, F.; Bonacina, F. Farmaco Ed. Sci. 1963, 18, 254
  8. Massarani, E.; Nardi, D.; Barzaghi, F.; Bonacina, F. Chem. Abstr. 1963, 59, 7467.
  9. Agarwal, A. K.; Gupta, M. L.; Bhargava, K. P.; Parmar, S. S. Res.Commun. Chem. Pathol. Pharmacol. 1978, 22, 625.
  10. Jurd, L.; Wong, R. Y. Aust. J. Chem. 1980, 33, 137. https://doi.org/10.1071/CH9800137
  11. Jurd, L. Aust. J. Chem. 1980, 33, 1603. https://doi.org/10.1071/CH9801603
  12. Antaki, H. J. Chem. Soc. 1963, 4877. https://doi.org/10.1039/jr9630004877
  13. Grinsteins, E. E.; Stankevich, E. I.; Duburs, G. Khim. Geterotsikl.Soedin. 1967, 395
  14. Grinsteins, E. E.; Stankevich, E. I.; Duburs, G. Chem. Abstr. 1969, 70, 87768.
  15. Stankevich, E. I.; Vanags, G. Zh. Obshch. Khim. 1962, 32, 1147
  16. Stankevich, E. I.; Vanags, G. Chem. Abstr. 1963, 58, 2429.
  17. Kidwai, M.; Sapra, P.; Bhushan, K. R.; Misra, P.; Saxena, R. K.;Gupta, R.; Singh, M. Bioorg. Chem. 2001, 29, 1380.
  18. Dittmer, D. C. Chem. and Ind. 1997, 779.
  19. Kidwai, M.; Rastogi, S.; Venkataramanan, R. Bull. Chem. Soc.Jpn. 2003, 76(1), 203. https://doi.org/10.1246/bcsj.76.203
  20. Kidwai, M.; Venkataramanan, R.; Dave, B. Green Chemistry2001, 3, 278. https://doi.org/10.1039/b106034c
  21. Kidwai, M.; Misra, P.; Bhushan, K. R. Synth. Commun. 2001,31(6), 9. https://doi.org/10.1081/SCC-100000173
  22. Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: Weinheim, 1994.
  23. Liagre, M.; Loupy, A.; Oussaid, A.; Petit, A.; Cleophax, J. Scalingup of some typical organic reactions under focussed microwaves,presented at the International Conference on Microwave Chemistry;Prague, Czech Republic, September 6-11, 1998.
  24. Hantzsch, A. Justus Liebigs Ann. Chem. 1882, 1, 215.
  25. Johnson, A. P.; Pelter, A. J. Chem. Soc. C 1966, 606. https://doi.org/10.1039/j39660000606
  26. Vanags, G.; Stankevich, E. I. Zh. Obshch. Khim. 1960, 30, 3287
  27. Vanags, G.; Stankevich, E. I. Chem. Abstr. 1961, 55, 21119.
  28. Zh. Obshch. Khim. v.30 Vanags, G.;Stankevich, E. I.
  29. Chem. Abstr. v.55 Vanags, G.;Stankevich, E. I.

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