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Carbon–SO3H derived from glycerol: a green recyclable catalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-ones

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Abstract

In this study, we have described a clean and facile condensation reaction of various aromatic aldehydes or cyclic ketones with 2-aminobenzamide under mild conditions in the presence of C–SO3H as an efficient catalyst derived from glycerol. This protocol furnishes an imperative avenue for the access of 2,3-dihydroquinazolin-4(1H)-ones in excellent yields with a range of structural diversity. The recovered catalyst has been engineered for subsequent runs with substantial activity.

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References

  1. D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 126, 11804 (2004)

    Article  CAS  Google Scholar 

  2. A. Domling, Chem. Rev. 106, 17 (2006)

    Article  Google Scholar 

  3. D.J. Raman, M. Yus, Angew. Chem. Int. Ed. 44, 1602 (2005)

    Article  Google Scholar 

  4. A. Corma, Chem. Rev. 95, 559 (1995)

    Article  CAS  Google Scholar 

  5. T. Okuhara, Chem. Rev. 102, 3641 (2002)

    Article  CAS  Google Scholar 

  6. B. Maheshwar Rao, G. Niranjan Reddy, T. Vijaikumar Reddy, B.L.A. Prabhavathi Devi, R.B.N. Prasad, J.S. Yadav, B.V. Subba Reddy, Tetrahedron Lett. 54, 2466 (2013)

    Article  CAS  Google Scholar 

  7. V. Manneganti, R.B.N. Prasad, B.L.A. Prabhavathi Devi, Eur. J. Chem. 5, 167 (2014)

    Article  Google Scholar 

  8. B.L.A. Prabhavathi Devi, K.N. Gangadhar, P.S.S. Prasad, B. Jagannadh, R.B.N. Prasad, Chemsuschem 2, 617 (2009)

    Article  CAS  Google Scholar 

  9. K.N. Gangadhar, M. Vijay, R.B.N. Prasad, B.L.A. Prabhavathi Devi, Green Sustain. Chem. 3, 122 (2013)

    Article  Google Scholar 

  10. G. Niranjan Reddy, B. Maheshwar Rao, M. Vijay, B.L.A. Prabhavathi Devi, R.B.N. Prasad, B.V. Subba Reddy, Can. J. Chem. 93, 341 (2015)

    Article  Google Scholar 

  11. M.G. Arania, M.S. Niasaria, S. Naseh, Ultrason. Sonochem. 39, 494 (2017)

    Article  Google Scholar 

  12. M.G. Arani, M.M. Arani, M.S. Niasari, J. Mol. Liq. 216, 59 (2016)

    Article  Google Scholar 

  13. H. Wang, S. Xue, J. Mater. Sci. Mater. Electron. 27, 1 (2016)

    Article  Google Scholar 

  14. M.G. Arani, M.M. Arani, M.S. Niasari, J. Mol. Catal. A Chem. 425, 31 (2016)

    Article  Google Scholar 

  15. L.N. Moghadam, M.S. Niasari, J. Mol. Struct. 1146, 629 (2017)

    Article  Google Scholar 

  16. H. Haghjooa, F.S. Sangsefidia, S.A. Hashemizadehb, M.S. Niasari, J. Mol. Liq. 225, 290 (2017)

    Article  Google Scholar 

  17. B.L.V. Prabhavathi Devi, T. Vijai Kumar Reddy, K. Vijaya Lakshmi, R.B.N. Prasad, Bioresour. Technol. 153, 370 (2014)

    Article  CAS  Google Scholar 

  18. P. Sivaguru, K. Parameswaran, M. Kiruthika, P. Vadivel, A. Lalitha, J. Iran. Chem. Soc. 12, 95 (2015)

    Article  CAS  Google Scholar 

  19. K. Revathy, A. Lalitha, J. Iran. Chem. Soc. 12, 2045 (2015)

    Article  CAS  Google Scholar 

  20. V. Murugan, M. Kulkarni, R.M. Anand, E.P. Kumar, B. Suresh, V.M. Reddy, Asian J. Chem. 18, 900 (2006)

    CAS  Google Scholar 

  21. G. Bonola, P.D. Re, M.J. Magistretti, E. Massarani, I. Setnikar, J. Med. Chem. 11, 1136 (1968)

    Article  CAS  Google Scholar 

  22. Rexall Drug Co., U.S. Patent 3257397 (1966)

  23. K. Okumura, T. Oine, Y. Yamada, G. Hayashi, M. Nakama, J. Med. Chem. 11, 348 (1968)

    Article  CAS  Google Scholar 

  24. M.J. Hour, L.J. Huang, S.C. Kuo, Y. Xia, K. Bastow, Y. Nakanishi, E. Hamel, K.H. Lee, J. Med. Chem. 43, 4479 (2000)

    Article  CAS  Google Scholar 

  25. H.L. Birch, G.M. Buckley, N. Davies, H.J. Dyke, E.J. Frost, P.J. Gilbert, D.R. Hannah, A.F. Haughan, M.J. Madigan, T. Morgan, W.R. Pitt, A.J. Ratcliffe, N.C. Ray, M.D. Richard, A. Sharpe, A.J. Taylor, J.M. Whitworth, S.C. Williams, Bioorg. Med. Chem. Lett. 15, 5335 (2005)

    Article  CAS  Google Scholar 

  26. E. Cohen, B. Klarberg, J.R. Vaughan, J. Am. Chem. Soc. 81, 5508 (1959)

    Article  CAS  Google Scholar 

  27. V. Alagarsamy, V.R. Solomon, M. Murugan, Bioorg. Med. Chem. 15, 4009 (2007)

    Article  CAS  Google Scholar 

  28. J.I. Levin, P.I. Chan, T. Bailey, A.S. Katocs, A.M. Venkatesan, Bioorg. Med. Chem. Lett. 4, 1141 (1994)

    Article  CAS  Google Scholar 

  29. Instituto De Angeli S.P.A. French Patent M 1893 (1963)

  30. Shulton Inc. U.S. Patent 3265697 (1966)

  31. N. Hirose, S. Kuriyama, S. Sohda, K. Sakaguchi, H. Yamamoto, Chem. Pharm. Bull. 21, 1005 (1973)

    Article  CAS  Google Scholar 

  32. S. Schramm, E. Schmitz, E. Grundemann, J. Prakt. Chem. 326, 279 (1984)

    Article  CAS  Google Scholar 

  33. J.P. Michael, Nat. Prod. Rep. 25, 166 (2008)

    Article  CAS  Google Scholar 

  34. V. Alagarsamy, V.R. Solomon, K. Dhanabal, Bioorg. Med. Chem. 15, 235 (2007)

    Article  CAS  Google Scholar 

  35. J. Imagawa, K. Sakai, Eur. J. Pharmacol. 131, 257 (1986)

    Article  CAS  Google Scholar 

  36. R.Q. Dempcy, E.B. Skibo, Biochemistry 30, 8480 (1991)

    Article  CAS  Google Scholar 

  37. M.S. Malamas, J. Millen, J. Med. Chem. 34, 1492 (1991)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  39. R. Ramesh, A. Lalitha, Res. Chem. Intermed. 41, 8009 (2015)

    Article  CAS  Google Scholar 

  40. R. Ramesh, S. Maheswari, S. Murugesan, R. Sandhiya, A. Lalitha, Res. Chem. Intermed. 41, 8233 (2015)

    Article  CAS  Google Scholar 

  41. R. Ramesh, P. Vadivel, S. Maheswari, A. Lalitha, Res. Chem. Intermed. 42, 7625 (2016)

    Article  CAS  Google Scholar 

  42. R. Ramesh, A. Lalitha, ChemistrySelect 1, 2085 (2016)

    Article  CAS  Google Scholar 

  43. R. Ramesh, R. Madhesh, J.G. Malecki, A. Lalitha, ChemistrySelect 1, 5196 (2016)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  45. CrysAlis RED, Oxford Diffraction Ltd. Version 1.171.37.35g

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

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

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Acknowledgements

R. Ramesh gratefully thank DST-Inspire Fellowship, New Delhi, India (No: DST/INSPIRE Fellowship/2012/690) for financial assistance.

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Authors and Affiliations

  1. Department of Chemistry, Periyar University, Periyar Palkalai Nagar, Salem, Tamil Nadu, 636 011, India

    Rathinam Ramesh, Gunasekaran Sankar & Appaswami Lalitha

  2. Department of Crystallography, University of Silesia, Szkolna 9, 40-007, Katowice, Poland

    Jan Grzegorz Malecki

Authors
  1. Rathinam Ramesh
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  2. Gunasekaran Sankar
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  3. Jan Grzegorz Malecki
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  4. Appaswami Lalitha
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Correspondence to Appaswami Lalitha.

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Ramesh, R., Sankar, G., Malecki, J.G. et al. Carbon–SO3H derived from glycerol: a green recyclable catalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-ones. J IRAN CHEM SOC 15, 1–9 (2018). https://doi.org/10.1007/s13738-017-1202-1

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