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Glycerol assisted eco-friendly strategy for the facile synthesis of 4,4′-(arylmethylene)bis(3-methyl-1H-pyrazol-5-ols) and 2-aryl-2,3-dihydroquinazolin-4(1H)-ones under catalyst-free conditions

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Abstract

This article describes glycerol mediated eco-friendly approaches for the convenient access of structurally diverse 4,4′-(arylmethylene)bis(3-methyl-1H-pyrazol-5-ol) and 2-aryl-2,3-dihydroquinazolin-4(1H)-one motifs under catalyst-free conditions. Prominent advantages include clean processes, atom-efficiency, simplicity of the work-up, neutral conditions, low-cost reaction medium, excellent product yield and solvent reusability, in addition to relatively shorter reaction times.

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References

  1. Y. Zhuang, X. Teng, Y. Wang, P. Liu, G. Li, W. Zhu, Org. Lett. 13, 1130 (2011)

    Article  CAS  Google Scholar 

  2. R. Bouley, M. Kumarasiri, Z. Peng, L.H. Otero, W. Song, M.A. Suckow, V.A. Schroeder, W.R. Wolter, E. Lastochkin, N.T. Antunes, H. Pi, S. Vakulenko, J.A. Hermoso, M. Chang, S. Mobashery, J. Am. Chem. Soc. 137, 1738 (2015)

    Article  CAS  Google Scholar 

  3. I. Khan, A. Ibrar, W. Ahmed, A. Saeed, Eur. J. Med. Chem. 90, 124 (2015)

    Article  CAS  Google Scholar 

  4. P.D. Leeson, B. Springthorpe, Nat. Rev. Drug Discovery 6, 881 (2007)

    Article  CAS  Google Scholar 

  5. B.N. Borse, S.R. Shukla, Y.A. Sonawane, Synth. Commun. 42, 412 (2012)

    Article  CAS  Google Scholar 

  6. J.F. Wolfe, T.L. Rathman, M.C. Sleevi, J.A. Campbell, T.D. Greenwood, J. Med. Chem. 33, 161 (1990)

    Article  CAS  Google Scholar 

  7. J.K. Padia, M. Field, J. Hinton, K. Meecham, J. Pablo, R. Pinnock, B.D. Roth, L. Singh, N.S. Chauhan, B.K. Trivedi, L. Webdale, J. Med. Chem. 41, 1042 (1998)

    Article  CAS  Google Scholar 

  8. F. He, P. Li, Y. Gu, G. Li, Green Chem. 11, 1767 (2009)

    Article  CAS  Google Scholar 

  9. H.R. Safaei, M. Shekouhy, S. Rahmanpur, A. Shirinfeshan, Green Chem. 14, 1696 (2012)

    Article  CAS  Google Scholar 

  10. C.S. Radatz, R.B. Silva, G. Perin, E.J. Lenardão, R.G. Jacob, D. Alves, Tetrahedron Lett. 52, 4132 (2011)

    Article  CAS  Google Scholar 

  11. K.U. Sadek, R.A. Mekheimed, A.M.A. Hameed, F. Elnahas, M.H. Elnagdi, Molecules 17, 6011 (2012)

    Article  CAS  Google Scholar 

  12. M. Shekouhya, A.M. Sarvestania, S. Khajeha, A.K. Nezhad, RSC Adv. 5, 63705 (2015)

    Article  Google Scholar 

  13. K.P. Nandre, J.K. Salunke, J.P. Nandre, V.S. Patil, A.U. Borse, S.V. Bhosale, Chin. Chem. Lett. 23, 161 (2012)

    Article  CAS  Google Scholar 

  14. V.B. Jagrut, D.L. Lingampalle, P.D. Netankar, W.N. Jadhav, Der Pharma Chemica 5, 8 (2013)

    CAS  Google Scholar 

  15. F. Nemati, M.M. Hosseini, H.Kiani, J. Saudi Chem. Soc. (2013). doi:10.1016/j.jscs.2013.02.004

    Google Scholar 

  16. M.F. Brana, A. Gradillas, A.G. Ovalles, Bioorg. Med. Chem. 14, 9 (2006)

    Article  CAS  Google Scholar 

  17. N. Uramaru, H. Shigematsu, A. Toda, R. Eyanagi, S. Kitamura, S. Ohta, J. Med. Chem. 53, 8727 (2010)

    Article  CAS  Google Scholar 

  18. D.M. Bailey, P.E. Hansen, A.G. Hlavac, E.R. Baizman, J. Pearl, A.F. Defelice, M.E. Feigenson, J. Med. Chem. 28, 256 (1985)

    Article  CAS  Google Scholar 

  19. K. Sujatha, G. Shanthi, N.P. Selvam, S. Manoharan, P.T. Perumal, M. Rajendran, Bioorg. Med. Chem. Lett. 19, 4501 (2009)

    Article  CAS  Google Scholar 

  20. D. Singh, D. Singh, J. Indian Chem. Soc. 68, 165 (1991)

    CAS  Google Scholar 

  21. J.J. Liu, M.Y. Zhao, X. Zhang, X. Zhao, H.L. Zhu, Mini Rev. Med. Chem. 13, 1957 (2013)

    Article  CAS  Google Scholar 

  22. S. Sugiura, S. Ohno, O. Ohtani, K. Izumi, T. Kitamikado, H. Asai, K. Kato, M. Hori, H. Fujimura, J. Med. Chem. 20, 80 (1977)

    Article  CAS  Google Scholar 

  23. D. Castagnolo, A.D. Logu, M. Radi, Bioorg. Med. Chem. 16, 8587 (2008)

    Article  CAS  Google Scholar 

  24. Y. Liu, G. He, C. Kai, Y. Li, H. Zhu, J. Heterocycl. Chem. 49, 1370 (2012)

    Article  CAS  Google Scholar 

  25. M. Londershausen, Pestic. Sci. 48, 269 (1996)

    Article  CAS  Google Scholar 

  26. R.C. Maurya, R. Verma, Indian J. Chem., Sect A 36, 596 (1997)

    Google Scholar 

  27. A.D. Garnovskii, A.I. Uraev, V.I. Minkin, Arkivoc 3, 29 (2004)

    Google Scholar 

  28. H. Nakagawa, R. Ohyama, A. Kimata, T. Suzuki, N. Miyata, Bioorg. Med. Chem. Lett. 16, 5939 (2006)

    Article  CAS  Google Scholar 

  29. P. Kessler, T. Aybek, G. Neidhart, S. Dogan, D.H. Bremerich, V. Lischke, C. Byhahan, J. Cardiothorac. Vasc. Anesth. 19, 32 (2005)

    Article  Google Scholar 

  30. W.S. Hamama, Synth. Commun. 31, 133 (2001)

    Article  Google Scholar 

  31. T. Ren, S. Liu, G. Li, J. Zhang, J. Guo, W. Li, L. Yang, Spectrochim. Acta, Part A 97, 167 (2012)

    Article  CAS  Google Scholar 

  32. 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 

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

    CAS  Google Scholar 

  34. 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 

  35. G. Bonola, R.P. Da, M.J. Magistretti, E. Massarani, I. Setnikar, J. Med. Chem. 11, 1136 (1968)

    Article  CAS  Google Scholar 

  36. Rexall Drug Co., U.S. Patent 3257397, 1966

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  40. J. Obniska, K. Shi, Acta Pol. Pharm. 63, 101 (2006)

    CAS  Google Scholar 

  41. 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 

  42. Instituto De Angeli S.p.A. French Patent M 1893, 1963

  43. Shulton Inc. U.S. Patent 3265697, 1966

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

    Article  CAS  Google Scholar 

  45. C. Mustazza, A. Borioni, I. Sestili, M. Sbraccia, A. Rodomonte, R. Ferretti, M.R. Giudice, Chem. Pharm. Bull. 54, 611 (2006)

    Article  CAS  Google Scholar 

  46. A.N. Gangwal, U.R. Kothawade, A.D. Galande, D.S. Pharande, A.S. Dhake, Indian. J. Heterocycl. Chem. 10, 291 (2001)

    CAS  Google Scholar 

  47. A.R. Raghu Ram, R.H. Bahekar, Indian J. Chem 38(B), 434 (1999)

    Google Scholar 

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

    Article  CAS  Google Scholar 

  49. L. He, H. Li, H. Chen, X.F. Wu, RSC Adv. 4, 12065 (2014)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  55. A. Vafaee, A. Davoodnia, M. Pordel, Res. Chem. Intermed. 41, 8343 (2015)

    Article  CAS  Google Scholar 

  56. Z. Zhou, Y. Zhang, Green Chem. Lett. Rev. 7, 18 (2014)

    Article  Google Scholar 

  57. J.S. Ghomi, B.K. Koopaei, H.S. Alavi, RSC Adv. 4, 46106 (2014)

    Article  Google Scholar 

  58. W. Wang, S.X. Wang, X.Y. Qin, J.T. Li, Synth. Commun. 35, 1263 (2005)

    Article  CAS  Google Scholar 

  59. M. Zarghani, B. Akhlaghinia, RSC Adv. 5, 87769 (2015)

    Article  CAS  Google Scholar 

  60. E. Soleimani, S. Ghorbani, M. Taran, A. Sarvary, C. R. Chimie 15, 955 (2012)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  62. J. Safari, S.G. Ravandi, J. Mol. Catal. A: Chem. 390, 1 (2014)

    Article  CAS  Google Scholar 

  63. A.G. Choghamarani, B. Tahmasbi, New J. Chem. 40, 1205 (2016)

    Article  Google Scholar 

  64. M. Rahman, I. Ling, N. Abdulah, R. Hashim, A. Hajra, RSC Adv. 5, 7755 (2015)

    Article  CAS  Google Scholar 

  65. N. Kausar, I. Roy, D. Chattopadhyay, A.R. Das, RSC Adv. 2016(6), 22320 (2016)

    Article  Google Scholar 

  66. M. Wang, J. Gao, Z. Song, L. Wang, J. Heterocyclic Chem. 49, 1250 (2012)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  68. J. Chen, W. Su, H. Wu, M. Liub, C. Jin, Green Chem. 9, 972 (2007)

    Article  CAS  Google Scholar 

  69. Y.X. Zong, Y. Zhao, W.C. Luo, X.H. Yu, J.K. Wang, Y. Pan, Chin. Chem. Lett. 21, 778 (2010)

    Article  CAS  Google Scholar 

  70. V.B. Labade, P.V. Shinde, M.S. Shingare, Tetrahedron Lett. 54, 5778 (2013)

    Article  CAS  Google Scholar 

  71. S.G. Zhang, Z.B. Xie, L.S. Liu, M. Liang, Z.G. Le, Chin. Chem. Lett. (2016). doi:10.1016/j.cclet.2016.06.001

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

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Acknowledgments

R. R. gratefully acknowledge the DST-Inspire Fellowship, New Delhi, India (No: DST/INSPIRE Fellowship/2012/690) for financial support.

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Authors and Affiliations

  1. Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, Periyar University, Periyar Palkalai Nagar, Salem, Tamil Nadu, 636011, India

    Rathinam Ramesh, Nagarajan Nagasundaram, Durairaj Meignanasundar & Appaswami Lalitha

  2. Department of Chemistry, Salem Sowdeswari College, Salem, Tamil Nadu, 636010, India

    Pullar Vadivel

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  1. Rathinam Ramesh
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  2. Nagarajan Nagasundaram
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Correspondence to Appaswami Lalitha.

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Ramesh, R., Nagasundaram, N., Meignanasundar, D. et al. Glycerol assisted eco-friendly strategy for the facile synthesis of 4,4′-(arylmethylene)bis(3-methyl-1H-pyrazol-5-ols) and 2-aryl-2,3-dihydroquinazolin-4(1H)-ones under catalyst-free conditions. Res Chem Intermed 43, 1767–1782 (2017). https://doi.org/10.1007/s11164-016-2728-z

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