Skip to main content
SpringerLink
Log in

Punica granatum peel: an organocatalyst for green and rapid synthesis of 3,4-dihydropyrimidin-2 (1H)-ones/thiones under solvent-free condition

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

A novel and green approach was adopted for the synthesis of 3,4-dihydropyrimidin-2(1H)-one/thiones derivatives using Punica granatum peel as an inexpensive, efficient and mild catalyst under solvent-free condition. The methodology is characterized by high efficiency, short reaction time, high yields, simple experimental procedure, availability of catalyst and environmentally friendly reaction conditions. Further, the catalyst can be reused and recovered seven times without significant decrease in its activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Scheme 2
Scheme 3
Fig. 5

Similar content being viewed by others

References

  1. D.L. da Silva, F.S. Reis, D.R. Muniz, A.L.T.G. Ruiz, J.E. de Carvalho, A.A. Sabino, L.V. Modolo, A. de Fatima, Bioorg. Med. Chem. 20, 2645 (2012)

    Article  CAS  Google Scholar 

  2. C.O. Kappe, Eur. J. Med. Chem. 35, 1043 (2000)

    Article  CAS  Google Scholar 

  3. K. Singh, K. Singh, Adv. Heterocycl. Chem. 105, 223 (2012)

    Article  CAS  Google Scholar 

  4. B.B. Tour, D.G. Hall, Chem. Rev. 109, 4439 (2009)

    Article  CAS  Google Scholar 

  5. L.F. Tietze, Chem. Rev. 96, 115 (1996)

    Article  CAS  Google Scholar 

  6. A. Dmling, I. Ugi, Angew. Chem. Int. Ed. Engl. 32, 563 (1993)

    Article  Google Scholar 

  7. A. Hasaninejad, A. Zare, M. Shekouly, J.A. Rad, J. Comb. Chem. 12, 844 (2010)

    Article  CAS  Google Scholar 

  8. S.K. Kundu, A. Majee, A. Hajra, Indian J. Chem. 48B, 408 (2009)

    CAS  Google Scholar 

  9. U.B. More, Asian J. Chem. 24, 1906 (2012)

    CAS  Google Scholar 

  10. J.T. Starcevich, T.J. Laughlin, R.S. Mohan, Tetrahedron Lett. 54, 983 (2013)

    Article  CAS  Google Scholar 

  11. H.N. Karade, J. Acharya, M.P. Kaushik, Tetrahedron Lett. 53, 5541 (2012)

    Article  CAS  Google Scholar 

  12. F. Shirini, M.A. Zolfigol, E. Mollarazi, Lett. Org. Chem. 2, 718 (2005)

    Article  CAS  Google Scholar 

  13. S.L. Jain, J.K. Joseph, B. Sain, Catal. Lett. 115, 52 (2007)

    Article  CAS  Google Scholar 

  14. X. Chen, Y. Peng, Catal. Lett. 122, 310 (2008)

    Article  CAS  Google Scholar 

  15. X. Hui, W. Yan-Guang, Chin. J. Chem. 21, 327 (2003)

    Article  Google Scholar 

  16. R.H. Shoar, G. Rahimzadeh, F. Derikvand, M. Farzaneh, Synth. Commun. 40, 1270 (2010)

    Article  CAS  Google Scholar 

  17. K. Bahrami, M.M. Khodaei, A. Nejati, Monatsh. Chem. 142, 159 (2011)

    Article  CAS  Google Scholar 

  18. S. Rostamnia, K. Lamei, Chin. Chem. Lett. 23, 930 (2012)

    Article  CAS  Google Scholar 

  19. A.G. Choghamarani, P. Zamani, Chin. Chem. Lett. 24, 804 (2013)

    Article  CAS  Google Scholar 

  20. S. Rostamnia, F. Pourhassan, Chin. Chem. Lett. 24, 401 (2013)

    Article  CAS  Google Scholar 

  21. M.A. Chari, K. Syamasundar, J. Mol. Catal. A Chem. 221, 137 (2004)

    Article  CAS  Google Scholar 

  22. C. Mukhopadhyay, P.K. Tapaswi, M.G.B. Drew, Tetrahedron Lett. 51, 3944 (2010)

    Article  CAS  Google Scholar 

  23. X.C. Wang, L.J. Zhang, Z. Zhang, Z.J. Quan, Chem. Lett. 23, 423 (2012)

    CAS  Google Scholar 

  24. M.A. Bigdeli, G. Gholami, E. Sheikhhosseini, Chem. Lett. 22, 903 (2011)

    CAS  Google Scholar 

  25. J. Mondal, T. Sen, A. Bhaumik, Dalton Trans. 41, 6173 (2012)

    Article  CAS  Google Scholar 

  26. J. Cheng, D.Y. Qi, Chin. Chem. Lett. 18, 647 (2007)

    Article  CAS  Google Scholar 

  27. K. Folkers, T.B. Johnson, J. Am. Chem. Soc. 55, 2886 (1933)

    Article  CAS  Google Scholar 

  28. S. Samai, G.C. Nandi, P. Singh, M.S. Singh, Tetrahedron 65, 10155 (2009)

    Article  CAS  Google Scholar 

  29. T.H. Niloofar, D. Abolghasem, Chin. J. Chem. 29, 203 (2011)

    Article  Google Scholar 

  30. S. Tu, X. Zhu, F. Shi, J. Zhang, Y. Zhang, J. Heterocycl. Chem. 44, 837 (2007)

    Article  CAS  Google Scholar 

  31. H. Sachdeva, R. Saroj, S. Khaturia, H.L. Singh, J. Chil. Chem. Soc. 57, 1012 (2012)

    Article  CAS  Google Scholar 

  32. Y. Wang, H. Yang, J. Yu, Z. Miao, R. Chena, Adv. Synth. Catal. 351, 3057 (2009)

    Article  CAS  Google Scholar 

  33. R.S. Bhosale, S.V. Bhosale, S.V. Bhosale, T. Wang, P.K. Zubaidha, Tetrahedron Lett. 45, 9111 (2004)

    Article  CAS  Google Scholar 

  34. S.E. Hankari, B. Motos-Perez, P. Hesemann, A. Bouhaouss, J.J.E. Moreau, Chem. Commun. 47, 6704 (2011)

    Article  CAS  Google Scholar 

  35. N. Prosa, R. Turgis, R. Piccardi, M.C. Scherrmann, Eur. J. Org. Chem. 11, 2188 (2012)

    Article  CAS  Google Scholar 

  36. D. Tejedor, F. Garcia-Tellado, Chem. Soc. Rev. 36, 484 (2007)

    Article  CAS  Google Scholar 

  37. L. Weber, Drug Discov. Today 7, 143 (2002)

    Article  CAS  Google Scholar 

  38. C. Hulme, V. Gore, Curr. Med. Chem. 10, 51 (2003)

    Article  CAS  Google Scholar 

  39. S.D. Sharma, P. Gogoi, D. Konwar, Green Chem. 9, 153 (2007)

    Article  Google Scholar 

  40. A.R. Gholap, K. Venkatesan, T. Daniel, R.J. Lahoti, K.V. Srinivasan, Green Chem. 6, 147 (2004)

    Article  CAS  Google Scholar 

  41. A.V. Patil, A.R. Karade, In T.K. Bose and S.K. Mitra (Eds.), Fruits: Tropical, Subtropical (Naya Prakash, Calcutta, 1996)

    Google Scholar 

  42. C. Bell, S. Hawthorne, J. Pharm. Pharmacol. 60, 139 (2008)

    Article  CAS  Google Scholar 

  43. M.K. Reddy, S.K. Gupta, M.R. Jacob, S.I. Khan, D. Ferreira, Planta Med. 73, 461 (2007)

    Article  CAS  Google Scholar 

  44. G.J. Kotwal, Vaccine 26, 3055 (2007)

    Article  CAS  Google Scholar 

  45. N.P. Seeram, L.S. Adams, S.M. Henning, Y. Niu, Y. Zhang, M.G. Nair, D. Heber, J. Nut. Biochem. 16, 360 (2005)

    Article  CAS  Google Scholar 

  46. P.S. Negi, G.K. Jayaprakash, B.S. Jena, Food Chem. 80, 393 (2003)

    Article  CAS  Google Scholar 

  47. N. Seeram, R. Lee, M. Hardy, D. Heber, Separ. Purif. Technol. 41, 49 (2005)

    Article  CAS  Google Scholar 

  48. M.N. Clifford, A. Scalbert, J. Sci. Food Agric. 80, 1118 (2000)

    Article  CAS  Google Scholar 

  49. N. Kamal, Amin. J. Hazard. Mater. 165, 52 (2009)

    Article  CAS  Google Scholar 

  50. A. Bhatnagar, A.K. Minocha, J. Hazard. Mater. 168, 1111 (2009)

    Article  CAS  Google Scholar 

  51. E.S.Z. El-Ashtoukhya, N.K. Amina, O. Abdelwahab, Desalination 223, 162 (2008)

    Article  CAS  Google Scholar 

  52. A. El Nemr, Chem. Ecol. 23, 409 (2007)

    Article  CAS  Google Scholar 

  53. A. El Nemr, J. Hazard. Mater. 161, 132 (2009)

    Article  CAS  Google Scholar 

  54. M. Rohani Moghadam, N. Nasirizadeh, Z. Dashti, E. Babanezhad, Int. J. Ind. Chem. 4, 19 (2013)

    Article  Google Scholar 

  55. A. Bhatnagar, A.K. Minocha, Colloids Surf. B Biointerfaces 76, 544 (2010)

    Article  CAS  Google Scholar 

  56. N. Razavi, B. Akhlaghinia, RSC Adv. 5, 12372 (2015)

    Article  CAS  Google Scholar 

  57. S.S.E. Ghodsinia, B. Akhlaghinia, RSC Adv. 5, 49849 (2015)

    Article  CAS  Google Scholar 

  58. M. Zarghani, B. Akhlaghinia, Appl. Organomet. Chem. 29, 683 (2015)

    Article  CAS  Google Scholar 

  59. Z. Zarei, B. Akhlaghinia, Chem. Pap. 69, 1421 (2015)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  61. N. Razavi, B. Akhlaghinia, New J. Chem. 40, 477 (2016)

    Article  CAS  Google Scholar 

  62. R. Jahanshahi, B. Akhlaghinia, RSC Adv. 5, 104087 (2015)

    Article  CAS  Google Scholar 

  63. N. Yousefi Siavashi, B. Akhlaghinia, M. Zarghani, Res. Chem. Intermed. 42, 5789 (2016)

    Article  CAS  Google Scholar 

  64. E. Karimian, B. Akhlaghinia, S.S.E. Ghodsinia, J. Chem. Sci. 128, 429 (2016)

    Article  CAS  Google Scholar 

  65. R. Jahanshahi, B. Akhlaghinia, RSC Adv. 6, 29210 (2016)

    Article  CAS  Google Scholar 

  66. M. Zarghani, B. Akhlaghinia, RSC Adv. 6, 31850 (2016)

    Article  CAS  Google Scholar 

  67. M. Zarghani, B. Akhlaghinia, RSC Adv. 6, 38592 (2016)

    Article  CAS  Google Scholar 

  68. S.S.E. Ghodsinia, B. Akhlaghinia, RSC Adv. 6, 63613 (2016)

    Article  CAS  Google Scholar 

  69. M. Zarghani, B. Akhlaghinia, Bull. Chem. Soc. Jpn 89, 1192 (2016)

    Article  CAS  Google Scholar 

  70. S. Memar Masjed, B. Akhlaghinia, M. Zarghani, N. Razavi, Aust. J. Chem. (2016). doi:10.1071/CH16126

    Google Scholar 

  71. Z. Zarei, B. Akhlaghinia, RSC Adv. 6, 106473 (2016)

    Article  CAS  Google Scholar 

  72. M. Abbasi, Res. Chem. Intermed. 42, 3303 (2016)

    Article  CAS  Google Scholar 

  73. A. Zare, Z. Nasouri, J. Mol. Liq. 216, 364 (2016)

    Article  CAS  Google Scholar 

  74. J. Safari, S. Gandomi-Ravandi, S. Ashiri, New J. Chem. 40, 512 (2016)

    Article  CAS  Google Scholar 

  75. Q. Song, X. An, F. Che, T. Shen, J. Heterocycl. Chem 52, 1496 (2015)

    Article  CAS  Google Scholar 

  76. H. Kiyani, M. Ghiasi, Res. Chem. Intermed. 41, 5177 (2015)

    Article  CAS  Google Scholar 

  77. F. Tamaddon, S. Moradi, J. Mol. Catal. A Chem. 370, 117 (2013)

    Article  CAS  Google Scholar 

  78. A. Rajack, K. Yuvaraju, Ch. Praveen, Y.L.N. Murthy, J. Mol. Catal. A Chem. 370, 197 (2013)

    Article  CAS  Google Scholar 

  79. C.J. Liu, J.D. Wang, Molecules 14, 763 (2009)

    Article  CAS  Google Scholar 

  80. S. Nagarajan, T.M. Sheikh, E. Kandasamy, J. Chem. Sci. 127, 1539 (2015)

    Article  CAS  Google Scholar 

  81. W. Li, G. Zhou, P. Zhang, Y. Lai, S. Xu, Heterocycles 83, 2067 (2011)

    Article  CAS  Google Scholar 

  82. F. Shaghayeghi Toosi, A. Maghsoodi, F.S. Toosi, Synth. React. Inorg. M. 46, 168 (2016)

    Article  CAS  Google Scholar 

  83. K. Akhter, K. Jahan, U.K.R. Romman, M.G. Ahmed, M.S. Rahman, M. Al-Amin, Asian J. Chem. 27, 2624 (2015)

    Article  CAS  Google Scholar 

  84. J. Safari, Z. Zarnegar, RSC Adv. 3, 17962 (2013)

    Article  CAS  Google Scholar 

  85. R.O.M.A. De Souza, E.T. Da Penha, H.M.S. Milagre, S.J. Garden, P.M. Esteves, M.N. Eberlin, O.A.C. Antunes, Chem. Eur. J. 15, 9799 (2009)

    Article  CAS  Google Scholar 

  86. P.K. Sahu, P.K. Sahu, D.D. Agarwal, RSC Adv. 3, 9854 (2013)

    Article  CAS  Google Scholar 

  87. J. Safari, Z. Zarnegar, M. Heydarian, J. Taibah Univ. Sci. 7, 17 (2013)

    Article  Google Scholar 

  88. M. Kargar, R. Hekmatshoar, A. Mostashari, Z. Hashemi, Catal. Commun. 15, 123 (2011)

    Article  CAS  Google Scholar 

  89. F. Damkaci, A. Szymaniak, J. Chem. Educ. 91, 943 (2014)

    Article  CAS  Google Scholar 

  90. X.W. Liu, K.K. Pasunooti, H. Chai, C.N. Jensen, B.K. Gorityala, S. Wang, Tetrahedron Lett. 52, 80 (2011)

    Article  CAS  Google Scholar 

  91. ChV Reddy, M. Mahesh, P.V.K. Raju, T.R. Babu, V.V.N. Reddy, Tetrahedron Lett. 43, 2657 (2002)

    Article  CAS  Google Scholar 

  92. S. Rao Jetti, A. Bhatewara, T. Kadre, S. Jain, Chin. Chem. Lett. 25, 469 (2014)

    Article  CAS  Google Scholar 

  93. D.L. da Silva, S.A. Fernandes, A.A. Sabino, A. de Fatima, Tetrahedron Lett. 52, 6328 (2011)

    Article  CAS  Google Scholar 

  94. M. Moosavifar, C. R. Chim. 15, 444 (2012)

    Article  CAS  Google Scholar 

  95. G.H. Mahdavinia, H. Sepehrian, Chin. Chem. Lett. 19, 1435 (2008)

    Article  CAS  Google Scholar 

  96. F. Zamani, E. Izadi, Catal. Commun. 42, 104 (2013)

    Article  CAS  Google Scholar 

  97. S. Patil, S.D. Jadhav, S.Y. Mane, Int. J. Org. Chem. 1, 125 (2011)

    Article  CAS  Google Scholar 

  98. R. Tayebee, B. Maleki, M. Ghadamgahi, Chin. J. Catal. 33, 659 (2012)

    Article  CAS  Google Scholar 

  99. M. Nasr-Esfahani, M. Montazerozohori, M. Aghel-Mirrezaee, H. Kashi, J. Chil. Chem. Soc. 59, 2311 (2014)

    Article  CAS  Google Scholar 

  100. S. Besoluk, M. Kukukislamoglu, M. Zengin, M. Arsalan, M. Nebioglu, Turk. J. Chem. 34, 411 (2010)

    CAS  Google Scholar 

  101. K. Aswin, S.S. Mansoor, K. Logaiya, P.N. Sudhan, R.N. Ahmed, J. Taibah Univ. Sci. 8, 236 (2014)

    Article  Google Scholar 

Download references

Acknowledgement

The authors gratefully acknowledge the partial support of this study by Ferdowsi University of Mashhad Research Council.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, Mashhad, 9177948974, Iran

    Narges Mohammadian & Batool Akhlaghinia

Authors
  1. Narges Mohammadian
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Batool Akhlaghinia
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Batool Akhlaghinia.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 12530 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mohammadian, N., Akhlaghinia, B. Punica granatum peel: an organocatalyst for green and rapid synthesis of 3,4-dihydropyrimidin-2 (1H)-ones/thiones under solvent-free condition. Res Chem Intermed 43, 3325–3347 (2017). https://doi.org/10.1007/s11164-016-2828-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-016-2828-9

Keywords

Search

Navigation