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Ultrasound aided solvent-free synergy: an improved synthetic approach to access 3,4-dihydropyrimidin-2(1H)-ones

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Abstract

A remarkably simple synthetic method has been described for the access of structurally diverse 3,4-dihydropyrimidin-2(1H)-ones in excellent yields in the presence of 2,4,6-trichloro-1,3,5-triazine (TCT) as an efficient source of hydrochloric acid under ultrasound radiation. In this tandem reaction, a range of aldehydes, β-diketo esters and urea were made to condense together via one-pot, solvent-free synthetic strategy. Use of metal-free catalyst, readily accessible substrates, high production rate and ease of work-up are the imperative features of this protocol.

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References

  1. S. Tang, Y.Y. Si, Z.P. Wang, K.R. Mei, X. Chen, J.Y. Cheng, J.S. Zheng, L. Liu, Angew. Chem. Int. Ed. 54, 5713 (2015)

    Article  CAS  Google Scholar 

  2. T. Yatabe, X. Jin, K. Yamaguchi, N. Mizuno, Angew. Chem. Int. Ed. 54, 13302 (2015)

    Article  CAS  Google Scholar 

  3. Y. Deng, W. Gong, J. He, J.Q. Yu, Angew. Chem. Int. Ed. 53, 6692 (2014)

    Article  CAS  Google Scholar 

  4. M. Yoshida, T. Mizuguchi, K. Namba, Angew. Chem. Int. Ed. 53, 14550 (2014)

    Article  CAS  Google Scholar 

  5. A. Nefzi, J.M. Ostresh, R.A. Houghten, Chem. Rev. 97, 449 (1997)

    Article  CAS  PubMed  Google Scholar 

  6. T.L. Ho, Tandem Organic Reactions. Wiley: New York (1992)

    Google Scholar 

  7. A. Agarwal, K. Srivastava, S.K. Puri, P.M.S. Chauhan, Bioorg. Med. Chem. Lett. 15, 531 (2005)

    Article  CAS  PubMed  Google Scholar 

  8. S.B. Katiyar, K. Srivastava, S.K. Puri, P.M.S. Chauhan, Bioorg. Med. Chem. Lett. 15, 4957 (2005)

    Article  CAS  PubMed  Google Scholar 

  9. M.A. Bigdeli, M.M. Heravi, G.H. Mahdavinia, Catal. Commun. 8, 1595 (2007)

    Article  CAS  Google Scholar 

  10. L.D. Luca, G. Giacomelli, A. Porcheddu, J. Org. Chem. 67, 6272 (2002)

    Article  CAS  PubMed  Google Scholar 

  11. G.V.M. Sharma, J.J. Reddy, P.S. Lakshmi, Tetrahedron Lett. 45, 7729 (2004)

    Article  CAS  Google Scholar 

  12. G.V.M. Sharma, K.L. Reddy, P.S. Lakshmi, P.R. Krishna, Synthesis 2006, 55 (2006)

  13. P. Sivaguru, P. Theerthagiri, A. Lalitha, Tetrahedron Lett. 56, 2203 (2015)

    Article  CAS  Google Scholar 

  14. R. Ramesh, S. Maheswari, M. Arivazhagan, J.G. Malecki, A. Lalitha, Tetrahedron Lett. 58, 3905 (2017)

    Article  CAS  Google Scholar 

  15. M. Sharma, S. Pandey, K. Chauhan, D. Sharma, B. Kumar, P.M.S. Chauhan, J. Org. Chem. 77, 929 (2012)

    Article  CAS  PubMed  Google Scholar 

  16. K. Harikumar, V. Rajendran, Ultrason. Sonochem 21, 208 (2014)

    Article  CAS  PubMed  Google Scholar 

  17. M. Nasrollahzadeh, A. Ehsani, A.R. Vartouni, Ultrason. Sonochem 21, 275 (2014)

    Article  CAS  PubMed  Google Scholar 

  18. R. Kuppa, V.S. Moholkar, Ultrason. Sonochem. 17, 123 (2010)

    Article  CAS  PubMed  Google Scholar 

  19. C.O. Kappe, J. Org. Chem. 62, 3109 (1997)

    Article  CAS  PubMed  Google Scholar 

  20. F. Bossert, W. Vater, Med. Res. Rev. 9, 291 (1989)

    Article  CAS  PubMed  Google Scholar 

  21. I.T. Phucho, A. Nongpiur, S. Tumtin, R. Nongrum, R.L. Nongkhlaw, Rasayan J. Chem. 2, 662 (2009)

    CAS  Google Scholar 

  22. K.I. Sakata, M. Someya, Y. Matsumoto, H. Tauchi, M. Kai, M. Toyota, M. Takagi, M. Hareyama, M. Fukushima, Cancer Sci. 102, 1712 (2011)

    Article  CAS  PubMed  Google Scholar 

  23. A.D. Patil, N.V. Kumar, W.C. Kokke, M.F. Bean, A.J. Freyer, C.D. Brosse, S. Mai, A. Truneh, D.J. Faulkner, B. Carte, A.L. Breen, R.P. Hertzberg, R.K. Johnson, J.W. Westley, B.C.M. Potts, J. Org. Chem. 60, 1182 (1995)

    Article  CAS  Google Scholar 

  24. B. Ramesh, C.M. Bhalgat, Eur. J. Med. Chem. 46, 1882 (2011)

    Article  CAS  PubMed  Google Scholar 

  25. H.M. Savanur, R.G. Kalkhambkar, G. Aridoss, K.K. Laali, Tetrahedron Lett. 57, 3029 (2016)

    Article  CAS  Google Scholar 

  26. D.P. Narayanan, A. Gopalakrishnan, Z. Yaakob, S. Sugunan, B.N. Narayanan, Arab. J. Chem. https://doi.org/10.1016/j.arabjc.2017.04.011 (2017)

    Article  Google Scholar 

  27. S. Zolfagharinia, E. Kolvari, N. Koukabi, Catal. Lett 147, 1551 (2017)

    Article  CAS  Google Scholar 

  28. M. Sheykhan, A. Yahyazadeh, L. Ramezani, Mol. Catal. 435, 166 (2017)

    Article  CAS  Google Scholar 

  29. E. Kolvari, N. Koukabi, O. Armandpour, Tetrahedron 70, 1383 (2014)

    Article  CAS  Google Scholar 

  30. A. Phukan, S.J. Borah, P. Bordoloi, K. Sharma, B.J. Borah, P.P. Sarmah, D. Dutta, Adv. Powder Technol. 28, 1585 (2017)

    Article  CAS  Google Scholar 

  31. K. Gong, H. Wang, S. Wang, X. Ren, Tetrahedron 71, 4830 (2015)

    Article  CAS  Google Scholar 

  32. A. Khorshidi, K. Tabatabaeian, H. Azizi, M.A. Hashjin, E.A. Gilandeh, RSC Adv. 7, 17732 (2017)

    Article  CAS  Google Scholar 

  33. P. Shen, M. Xu, D. Yin, S. Xie, C. Zhou, F. Li, Catal. Commun. 77, 18 (2016)

    Article  CAS  Google Scholar 

  34. E. Kolvari, N. Koukabi, M.M. Hosseini, M. Vahidian, E. Ghobadi, RSC Adv. 6, 7419 (2016)

    Article  CAS  Google Scholar 

  35. D. Bhuyan, M. Saikia, L. Saikia, Microporous Mesoporous Mater. 256, 39 (2018)

    Article  CAS  Google Scholar 

  36. B.H. Rotstein, S. Zaretsky, V. Rai, A.K. Yudin, Chem. Rev. 114, 8323 (2014)

    Article  CAS  PubMed  Google Scholar 

  37. R.C. Cioc, E. Ruijter, R.V.A. Orru, Green Chem. 16, 2958 (2014)

    Article  CAS  Google Scholar 

  38. R. Ramesh, A. Lalitha, RSC Adv. 5, 51188 (2015)

    Article  CAS  Google Scholar 

  39. R. Ramesh, N. Nagasundaram, D. Meignanasundar, A. Lalitha, Res. Chem. Intermed. 43, 1767 (2017)

    Article  CAS  Google Scholar 

  40. R. Ramesh, P. Kalisamy, J.G. Malecki, A. Lalitha, Synlett 29, 203 (2018)

    Article  CAS  Google Scholar 

  41. R. Ramesh, G. Sankar, J.G. Malecki, A. Lalitha, J. Iran. Chem. Soc. 15, 1 (2018)

    Article  CAS  Google Scholar 

  42. R. Ramesh, D. Meignanasundar, A. Lalitha, ChemistrySelect 2, 10210 (2017)

    Article  CAS  Google Scholar 

  43. O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A.K. Howard, H.J. Puschmann, J. Appl. Cryst. 42, 339 (2009)

    Article  CAS  Google Scholar 

  44. G.M. Sheldrick, Acta Cryst A64, 112 (2008)

    Article  CAS  Google Scholar 

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Acknowledgements

R. Ramesh (IF120729) gratefully thank the financial assistance from Department of Science and Technology (Grant No: DST/INSPIRE Fellowship/2012/690) New Delhi, India.

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Correspondence to Appaswami Lalitha.

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Ramesh, R., Ramesh, S., Malecki, J.G. et al. Ultrasound aided solvent-free synergy: an improved synthetic approach to access 3,4-dihydropyrimidin-2(1H)-ones. J IRAN CHEM SOC 16, 1197–1205 (2019). https://doi.org/10.1007/s13738-019-01597-3

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