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Si-Fe Catalyzed Biginelli Reaction : A Versatile Method for the Synthesis of Dihydropyrimidinones

Authors(4) :-Kishan P. Haval, Ravibhushan S. Kulkarni, Pramod S. Phatak, Radhakrishnan M. Tigote

Dihydropyrimidinones were prepared involving Biginelli reaction of various aldehydes, urea/thiourea and ethyl acetoacetate in the presence of a heterogeneous Si-Fe catalyst.
Kishan P. Haval, Ravibhushan S. Kulkarni, Pramod S. Phatak, Radhakrishnan M. Tigote
Biginelli Reaction, Multicomponent Reactions, Si-Fe Catalyst, Dihydropyrimidinone.
  1. (a) Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360?413. (b) Suresh, Sandhu, J. S. Arkivoc, 2012, 66, 133. (c) Phucho, I. T.; Nongpiur, A.; Tumtin, S.; Nongrum R.; Nongkhlaw R. L. Rasayan J. Chem. 2009, 2, 662.
  2. Kappe, C. O. Acc. Chem. Res. 2000, 33, 879?888.
  3. Lusch, M. J.; Tallarico, J. A. Org. Lett. 2004, 6, 3237?3240.
  4. (a) Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043. (b) Kappe, C. O.; Shishkin, O.; Uray, G.; Verdino, P. Tetrahedron 2000, 56, 1859.
  5. Snider, B. B.; Shi, Z. J. J. Org. Chem. 1993, 58, 3828.
  6. (a) Folkers, K.; Harwood, H. J.; Johnson, T. B. J. Am. Chem. Soc. 1932, 54, 3751. (b) Wipf, P.; Cunningham, A. Tetrahedron Lett. 1995, 36, 7819. (c) Folkers, K.; Johnson, T. B. J. Am. Chem. Soc. 1934, 1180.
  7. (a) O’Reilly, B. C.; Atwal, K. S. Heterocycles 1987, 26, 1185. (b) Atwal, K. S.; O’Reilley, B. C.; Gougoutas, J. Z.; Malley, M. F. Heterocycles 1987, 26, 1189. (c) Shutalev, A. D.; Kuksa, V. A. Khim. Geterotsikl. Soedin. 1997, 105. (d) Shutalev, A. D.; Kishko, E. A.; Sivova, N.; Kuznetsov, A. Y. Molecules 1998, 3, 100.
  8. Choudhary, V. R.; Tillu, V. H.; Narkhede, V. S.; Borate, H. B.; Wakharkar, R. D. Catal. Commun. 2003, 4, 449.
  9. Shao, G. Q.; Chin. J. Synth. Chem. 2004, 12, 325.
  10. Manjula, A.; Rao, B. V.; Neelakantan, P. Synth. Commun. 2004, 34, 2665.
  11. Jenner, G. Tetrahedron Lett. 2004, 45, 6195.
  12. Gangadasu, B.; Palaniappan, S.; Rao, V. J. Synlett 2004, 1285.
  13. Russowsky, D.; Lopes, F. A.; da Silva, V. S. S.; Canto, K. F. S.; D’Oca, M. G. M.; Godoi, M. N. J. Braz. Chem. Soc. 2004, 15, 165.
  14. Tu, S.; Fang, F.; Zhu, S.; Li, T.; Zhang, X.; Zhuang, Q. J. Heterocycl. Chem. 2004, 41, 253.
  15. Shaabani, A.; Bazgir, A.; Bijanzadeh, H. R. Mol. Divers. 2004, 8, 141.
  16. Tu, S.; Fang, F.; Zhu, S.; Li, T.; Zhang, X.; Zhuang, Q. Synlett 2004, 537.
  17. Kappe, C. O.; Stadler, A. Org. React. 2004, 63, 1.
  18. Yadav, J. S.; Reddy, B. V. S.; Sridhar, P.; Reddy, J. S. S.; Nagaiah, K.; Lingaiah, N.; Saiprasad, P. S. Eur. J. Org. Chem. 2004, 552.
  19. (a) Gupta, R.; Gupta, A. K.; Paul, S.; Kachroo, P. L. Indian J. Chem. 1995, 34B, 151; (b) Yadav, J. S.; Subba Reddy, B. V.; Jagan Reddy, E.; Ramalingam, T. J. Chem. Res., Synop. 2000, 354.
  20. Adharvana Chari, M.; Syamasundar, K. J. Mol. Catal. A: Chem. 2004, 221, 137 and the references cited therein.
  21. (a) Amini, M. M.; Shaabani, A.; Bazgir, A. Catal. Commun. 2006, 7, 843. (b) Chen, Qin, S.; Jin, J. Catal. Commun. 2007, 8, 123. (c) Legeay, J. C.; Vanden Eynde, J. J.; Bazureau, J. P. Tetrahedron Lett. 2007, 48, 1063. (d) Kumar, A.; Maurya, R. A. Tetrahedron Lett. 2007, 48, 4569.
  22. Kappe, C. O. J. Org. Chem. 1997, 62, 7201.
  23. (a) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356. (b) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566.
  24. Huang, Y.; Yang, F.; Zhu, C. J. Am. Chem. Soc. 2005, 127, 16386.
  25. Huang, Y.; Yang, F.; Zhu, C. J. Am. Chem. Soc. 2006, 128, 14802.
  26. (a) Haval, K. P.; Argade N. P. J. Org. Chem. 2008, 73, 6936. (b) Haval, K. P.; Argade N. P. Synthesis 2007, 2198. (c) Haval, K. P.; Mhaske, S. B.; Argade N. P. Tetrahedron 2006, 62, 937. (d) Haval, K. P.; Argade N. P. Tetrahedron 2006, 62, 3557. (e) Tigote, R. M.; Haval, K. P.; Kazi, S. K. J. Med. Chem. & Drug Discovery 2017, 2, 654. (f) Shinde, N. V.; Dhake, A. S.; Haval K. P. Oriental Journal of Chemistry, 2016, 32, 515. (g) Shinde, N. V.; Dhake, A. S.; Haval K. P. Der Pharma Chemica, 2015, 7, 251
  27. Borate, H. B.; Gaikwad, A. G.; Maujan, S. R.; Sawargave, S. P.; Kalal, K. M. Tetrahedron Lett. 2007, 48, 4869.
Publication Details
  Published in : Volume 3 | Issue 9 | November-December 2017
  Date of Publication : 2017-12-15
License:  This work is licensed under a Creative Commons Attribution 4.0 International License.
Page(s) : 24-26
Manuscript Number : IJSRST173906
Publisher : Technoscience Academy
PRINT ISSN : 2395-6011
ONLINE ISSN : 2395-602X
Cite This Article :
Kishan P. Haval, Ravibhushan S. Kulkarni, Pramod S. Phatak, Radhakrishnan M. Tigote, "Si-Fe Catalyzed Biginelli Reaction : A Versatile Method for the Synthesis of Dihydropyrimidinones", International Journal of Scientific Research in Science and Technology(IJSRST), Print ISSN : 2395-6011, Online ISSN : 2395-602X, Volume 3, Issue 9, pp.24-26, November-December-2017.
Journal URL : http://ijsrst.com/IJSRST173906

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