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Journal of the Iranian Chemical Society

, Volume 15, Issue 1, pp 1–9 | Cite as

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

  • Rathinam Ramesh
  • Gunasekaran Sankar
  • Jan Grzegorz Malecki
  • Appaswami Lalitha
Original Paper

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.

Graphical Abstract

Keywords

Carbon–SO32,3-Dihydroquinazolin-4(1H)-ones Catalyst reusability Green synthesis X-ray crystals 

Notes

Acknowledgements

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

Supplementary material

13738_2017_1202_MOESM1_ESM.doc (529 kb)
Supplementary material 1 (DOC 529 kb)
13738_2017_1202_MOESM2_ESM.cif (207 kb)
Supplementary material 2 (CIF 206 kb)
13738_2017_1202_MOESM3_ESM.cif (442 kb)
Supplementary material 3 (CIF 441 kb)

References

  1. 1.
    D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 126, 11804 (2004)CrossRefGoogle Scholar
  2. 2.
    A. Domling, Chem. Rev. 106, 17 (2006)CrossRefGoogle Scholar
  3. 3.
    D.J. Raman, M. Yus, Angew. Chem. Int. Ed. 44, 1602 (2005)CrossRefGoogle Scholar
  4. 4.
    A. Corma, Chem. Rev. 95, 559 (1995)CrossRefGoogle Scholar
  5. 5.
    T. Okuhara, Chem. Rev. 102, 3641 (2002)CrossRefGoogle Scholar
  6. 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)CrossRefGoogle Scholar
  7. 7.
    V. Manneganti, R.B.N. Prasad, B.L.A. Prabhavathi Devi, Eur. J. Chem. 5, 167 (2014)CrossRefGoogle Scholar
  8. 8.
    B.L.A. Prabhavathi Devi, K.N. Gangadhar, P.S.S. Prasad, B. Jagannadh, R.B.N. Prasad, Chemsuschem 2, 617 (2009)CrossRefGoogle Scholar
  9. 9.
    K.N. Gangadhar, M. Vijay, R.B.N. Prasad, B.L.A. Prabhavathi Devi, Green Sustain. Chem. 3, 122 (2013)CrossRefGoogle Scholar
  10. 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)CrossRefGoogle Scholar
  11. 11.
    M.G. Arania, M.S. Niasaria, S. Naseh, Ultrason. Sonochem. 39, 494 (2017)CrossRefGoogle Scholar
  12. 12.
    M.G. Arani, M.M. Arani, M.S. Niasari, J. Mol. Liq. 216, 59 (2016)CrossRefGoogle Scholar
  13. 13.
    H. Wang, S. Xue, J. Mater. Sci. Mater. Electron. 27, 1 (2016)CrossRefGoogle Scholar
  14. 14.
    M.G. Arani, M.M. Arani, M.S. Niasari, J. Mol. Catal. A Chem. 425, 31 (2016)CrossRefGoogle Scholar
  15. 15.
    L.N. Moghadam, M.S. Niasari, J. Mol. Struct. 1146, 629 (2017)CrossRefGoogle Scholar
  16. 16.
    H. Haghjooa, F.S. Sangsefidia, S.A. Hashemizadehb, M.S. Niasari, J. Mol. Liq. 225, 290 (2017)CrossRefGoogle Scholar
  17. 17.
    B.L.V. Prabhavathi Devi, T. Vijai Kumar Reddy, K. Vijaya Lakshmi, R.B.N. Prasad, Bioresour. Technol. 153, 370 (2014)CrossRefGoogle Scholar
  18. 18.
    P. Sivaguru, K. Parameswaran, M. Kiruthika, P. Vadivel, A. Lalitha, J. Iran. Chem. Soc. 12, 95 (2015)CrossRefGoogle Scholar
  19. 19.
    K. Revathy, A. Lalitha, J. Iran. Chem. Soc. 12, 2045 (2015)CrossRefGoogle Scholar
  20. 20.
    V. Murugan, M. Kulkarni, R.M. Anand, E.P. Kumar, B. Suresh, V.M. Reddy, Asian J. Chem. 18, 900 (2006)Google Scholar
  21. 21.
    G. Bonola, P.D. Re, M.J. Magistretti, E. Massarani, I. Setnikar, J. Med. Chem. 11, 1136 (1968)CrossRefGoogle Scholar
  22. 22.
    Rexall Drug Co., U.S. Patent 3257397 (1966)Google Scholar
  23. 23.
    K. Okumura, T. Oine, Y. Yamada, G. Hayashi, M. Nakama, J. Med. Chem. 11, 348 (1968)CrossRefGoogle Scholar
  24. 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)CrossRefGoogle Scholar
  25. 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)CrossRefGoogle Scholar
  26. 26.
    E. Cohen, B. Klarberg, J.R. Vaughan, J. Am. Chem. Soc. 81, 5508 (1959)CrossRefGoogle Scholar
  27. 27.
    V. Alagarsamy, V.R. Solomon, M. Murugan, Bioorg. Med. Chem. 15, 4009 (2007)CrossRefGoogle Scholar
  28. 28.
    J.I. Levin, P.I. Chan, T. Bailey, A.S. Katocs, A.M. Venkatesan, Bioorg. Med. Chem. Lett. 4, 1141 (1994)CrossRefGoogle Scholar
  29. 29.
    Instituto De Angeli S.P.A. French Patent M 1893 (1963)Google Scholar
  30. 30.
    Shulton Inc. U.S. Patent 3265697 (1966)Google Scholar
  31. 31.
    N. Hirose, S. Kuriyama, S. Sohda, K. Sakaguchi, H. Yamamoto, Chem. Pharm. Bull. 21, 1005 (1973)CrossRefGoogle Scholar
  32. 32.
    S. Schramm, E. Schmitz, E. Grundemann, J. Prakt. Chem. 326, 279 (1984)CrossRefGoogle Scholar
  33. 33.
    J.P. Michael, Nat. Prod. Rep. 25, 166 (2008)CrossRefGoogle Scholar
  34. 34.
    V. Alagarsamy, V.R. Solomon, K. Dhanabal, Bioorg. Med. Chem. 15, 235 (2007)CrossRefGoogle Scholar
  35. 35.
    J. Imagawa, K. Sakai, Eur. J. Pharmacol. 131, 257 (1986)CrossRefGoogle Scholar
  36. 36.
    R.Q. Dempcy, E.B. Skibo, Biochemistry 30, 8480 (1991)CrossRefGoogle Scholar
  37. 37.
    M.S. Malamas, J. Millen, J. Med. Chem. 34, 1492 (1991)CrossRefGoogle Scholar
  38. 38.
    R. Ramesh, A. Lalitha, RSC Adv. 5, 51188 (2015)CrossRefGoogle Scholar
  39. 39.
    R. Ramesh, A. Lalitha, Res. Chem. Intermed. 41, 8009 (2015)CrossRefGoogle Scholar
  40. 40.
    R. Ramesh, S. Maheswari, S. Murugesan, R. Sandhiya, A. Lalitha, Res. Chem. Intermed. 41, 8233 (2015)CrossRefGoogle Scholar
  41. 41.
    R. Ramesh, P. Vadivel, S. Maheswari, A. Lalitha, Res. Chem. Intermed. 42, 7625 (2016)CrossRefGoogle Scholar
  42. 42.
    R. Ramesh, A. Lalitha, ChemistrySelect 1, 2085 (2016)CrossRefGoogle Scholar
  43. 43.
    R. Ramesh, R. Madhesh, J.G. Malecki, A. Lalitha, ChemistrySelect 1, 5196 (2016)CrossRefGoogle Scholar
  44. 44.
    R. Ramesh, N. Nagasundaram, D. Meignanasundar, A. Lalitha, Res. Chem. Intermed. 43, 1767 (2017)CrossRefGoogle Scholar
  45. 45.
    CrysAlis RED, Oxford Diffraction Ltd. Version 1.171.37.35gGoogle Scholar
  46. 46.
    O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A.K. Howard, H. Puschmann, J. Appl. Cryst. 42, 339 (2009)CrossRefGoogle Scholar
  47. 47.
    G.M. Sheldrick, Acta Cryst. A64, 112 (2008)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2017

Authors and Affiliations

  1. 1.Department of ChemistryPeriyar UniversitySalemIndia
  2. 2.Department of CrystallographyUniversity of SilesiaKatowicePoland

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