Skip to main content
SpringerLink
Log in

Phthalimide-N-sulfonic acid: a new and efficient organocatalyst for the Biginelli reaction under solvent-free conditions

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

Abstract

Phthalimide-N-sulfonic acid (PISA) was straightforwardly synthesized via addition of chlorosulfonic acid to a solution of potassium phthalimide in dry dichloromethane. This reagent is found to be an efficient solid acidic catalyst in the Biginelli reaction. The three-component reaction of aryl aldehydes, urea/thiourea, and ethyl acetoacetate or acetylacetone occurs by means of 10 mol % of PISA in solvent-free reaction conditions (SFRCs) at 120 °C. The present methodology is a green approach to access a series of 3,4-dihydropyrimidin-2(1H)-ones/thiones in high yields. In addition, the use of PISA as the catalyst offers several notable features such as simple operational procedure, no use of hazardous organic solvents, and recyclability of catalyst.

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
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. A. Crespo, A. El Maatougui, P. Biagini, J. Azuaje, A. Coelho, J. Brea, M.I. Loza, M.I. Cadavid, X. García-Mera, H. Gutiérrez-de-Terán, E. Sotelo, ACS Med. Chem. Lett. 4, 1031 (2013)

    Article  CAS  Google Scholar 

  2. A. Singh, T. Raj, T. Aree, N. Singh, Inorg. Chem. 52, 13830 (2013)

    Article  CAS  Google Scholar 

  3. M. Oliverio, P. Costanzo, M. Nardi, I. Rivalta, A. Procopio, ACS Sustain. Chem. Eng. 2, 1228 (2014)

    Article  CAS  Google Scholar 

  4. H.G.O. Alvim, T.B. de Lima, H.C.B. de Oliveira, F.C. Gozzo, J.L. de Macedo, P.V. Abdelnur, W.A. Silva, B.A.D. Neto, ACS Catal. 3, 1420 (2013)

    Article  CAS  Google Scholar 

  5. H.G.O. Alvim, T.B. Lima, A.L. de Oliveira, H.C.B. de Oliveira, F.M. Silva, F.C. Gozzo, R.Y. Souza, W.A. da Silva, B.A.D. Neto, J. Org. Chem. 79, 3383 (2014)

    Article  CAS  Google Scholar 

  6. L.M. Ramos, A.Y.P.L. Tobio, M.R. dos Santos, H.C.B. de Oliveira, A.F. Gomes, F.C. Gozzo, A.L. de Oliveira, B.A.D. Neto, J. Org. Chem. 77, 10184 (2012)

    Article  CAS  Google Scholar 

  7. N. Li, X.-H. Chen, J. Song, S.-W. Luo, W. Fan, L.-Z. Gong, J. Am. Chem. Soc. 131, 15301 (2009)

    Article  CAS  Google Scholar 

  8. X.-H. Chen, X.-Y. Xu, H. Liu, L.-F. Cun, L.-Z. Gong, J. Am. Chem. Soc. 128, 14802 (2006)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  10. D. Elhamifar, A. Shabani, Chem. Eur. J. 20, 3212 (2014)

    Article  CAS  Google Scholar 

  11. L.M. Ramos, B.C. Guido, C.C. Nobrega, J.R. Correa, R.G. Silva, H.C.B. de Oliveira, A.F. Gomes, F.C. Gozzo, B.A.D. Neto, Chem. Eur. J. 19, 4156 (2013)

    Article  CAS  Google Scholar 

  12. Y. Qiu, H. Sun, Z. Ma, W. Xia, J. Mol. Catal. A: Chem. 392, 76 (2014)

    Article  CAS  Google Scholar 

  13. C. Zhu, B. Yang, Y. Zhao, C. Fu, L. Tao, Y. Wei, Polym. Chem. 4, 5395 (2013)

    Article  CAS  Google Scholar 

  14. S. Rostamnia, A. Morsali, RSC Adv. 4, 10514 (2014)

    Article  CAS  Google Scholar 

  15. A. Keivanloo, M. Mirzaee, M. Bakherad, A. Soozani, Chin. J. Catal. 35, 362 (2014)

    Article  CAS  Google Scholar 

  16. J. Safari, Z. Zarnegar, New J. Chem. 38, 358 (2014)

    Article  CAS  Google Scholar 

  17. A. Mobinikhaledi, T. Mosleh, N. Foroughifar, Res. Chem. Intermed. (2013), in press, doi:10.1007/s11164-013-1406-7

  18. N.M. Khalifa, A.A.-H. Abdel-Rahman, S.I. Abd-Elmoez, O.A. Fathalla, A.A. Abd El-Gwaad, Res. Chem. Intermed. (2013), in press, doi:10.1007/s11164-013-1347-1

  19. P. Karthikeyan, S.S. Kumar, A.S. Arunrao, M.P. Narayan, P.R. Bhagat, Res. Chem. Intermed. 39, 1335 (2013)

    Article  CAS  Google Scholar 

  20. P. Biginelli, Gazz. Chim. Ital. 23, 360 (1893)

    Google Scholar 

  21. T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S.L. Schreiber, T.J. Mitchison, Science 286, 971 (1999)

    Article  CAS  Google Scholar 

  22. Z. Maliga, T.M. Kapoor, T.J. Mitchison, Chem. Biol. 9, 989 (2002)

    Article  CAS  Google Scholar 

  23. J.C. Barrow, P.G. Nantermet, H.G. Selnick, K.L. Glass, K.E. Rittle, K.F. Gilbert, T.G. Steele, C.F. Homnick, R.M. Freidinger, R.W. Ransom, P. Kling, D. Reiss, T.P. Broten, T.W. Schorn, R.S. Chang, S.S. O’Malley, T.V. Olah, J.D. Ellis, A. Barrish, K. Kassahun, P. Leppert, D. Nagarathnam, C. Forray, J. Med. Chem. 43, 2703 (2000)

    Article  CAS  Google Scholar 

  24. C. Goldstein, J.C. Schroeder, J.P. Fortin, J.M. Goss, S.E. Schaus, M. Beinborn, A.S. Kopin, J. Pharm. Exp. Ther. 335, 799 (2010)

    Article  CAS  Google Scholar 

  25. K.S. Atwal, B.N. Swanson, S.E. Unger, D.M. Floyd, S. Moreland, A. Hedberg, B.C. O’Reilly, J. Med. Chem. 34, 806 (1991)

    Article  CAS  Google Scholar 

  26. M. Matache, C. Dobrota, N.D. Bogdan, I. Dumitru, L.L. Ruta, C.C. Paraschivescu, I.C. Farcasanu, I. Baciu, D.P. Funeriu, Tetrahedron 65, 5949 (2009)

    Article  CAS  Google Scholar 

  27. T.N. Akhaja, J.P. Raval, Design. Chin. Chem. Lett. 23, 446 (2012)

    Article  CAS  Google Scholar 

  28. C.O. Kappe, Tetrahedron 49, 6937 (1993)

    Article  CAS  Google Scholar 

  29. C.O. Kappe, Acc. Chem. Res. 33, 879 (2000)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  31. K.S. Atwal, G.C. Rovnyak, S.D. Kimball, D.M. Floyd, S. Moreland, B.N. Swanson, J.Z. Gougoutas, J. Schwartz, K.M. Smillie, M.F. Malley, J. Med. Chem. 33, 2629 (1990)

    Article  CAS  Google Scholar 

  32. R. Zabihollahi, A. Fassihi, M.R. Aghasadeghi, H.R. Memarian, M. Soleimani, K. Majidzadeh-A, Med. Chem. Res. 22, 1270 (2013)

    Article  CAS  Google Scholar 

  33. J.S. Suresh, Sandhu. Arkivoc i 2012, 66 (2012)

    Google Scholar 

  34. M. Syamala, Org. Prep. Proced. Int. 41, 1 (2009)

    Article  CAS  Google Scholar 

  35. K. Singh, K. Singh, Advances in heterocyclic chemistry, Biginelli condensation: synthesis and structure diversification of 3,4-dihydropyrimidin-2(1H)-one derivatives, vol. 105 (2012) Ch: 3, pp. 223–308

  36. M.S. Singh, S. Chowdhury, RSC Adv. 2, 4547 (2012)

    Article  CAS  Google Scholar 

  37. R.P. Gore, A.P. Rajput, Drug Invent. Today 5, 148 (2013)

    Article  CAS  Google Scholar 

  38. M.M. Heravi, S. Asadi, B. Malekzadeh Lashkariani, Mol. Divers. (2013), in press, doi:10.1007/s11030-013-9439-9

  39. N. Isambert, M.D.S. Duque, J.C. Plaquevent, Y. Génisson, J. Rodriguez, T. Constantieux, Chem. Soc. Rev. 40, 1347 (2011)

    Article  CAS  Google Scholar 

  40. M.A. Kolosov, V.D. Orlov, D.A. Beloborodov, V.V. Dotsenko, Mol. Divers. 13, 5 (2009)

    Article  CAS  Google Scholar 

  41. M.J. Climent, A.C.S. Iborra, RSC Adv. 2, 16 (2012)

    Article  CAS  Google Scholar 

  42. S.S. Panda, P. Khanna, L. Khanna, Curr. Org. Chem. 16, 507 (2012)

    Article  CAS  Google Scholar 

  43. M. Pramanik, A. Bhaumik, ACS Appl. Mater. Interfaces 6, 933 (2014)

    Article  CAS  Google Scholar 

  44. Y.L.N. Murthy, A. Rajack, K. Yuvaraj, Arab. J. Chem. (2012), in press, doi:10.1016/j.arabjc.2012.04.046

  45. S. Imtiaz, M.A. Khan, A. Sharif, E. Ahmed, W.-O. Lin, M.A. Munawar, J. Chin. Chem. Soc. 59, 1446 (2012)

    Article  CAS  Google Scholar 

  46. K. Aswin, S.S. Mansoor, K. Logaiya, S.P.N. Sudhanetal, J. King Saud Univ. Sci. (2013), in press, doi:10.1016/j.jksus.2013.05.004

  47. A. Zhu, Q. Li, L. Li, J. Wang, Catal. Lett. 143, 463 (2013)

    Article  CAS  Google Scholar 

  48. N. Gangwar, V.K. Kasana, Med. Chem. Res. 21, 4506 (2012)

    Article  CAS  Google Scholar 

  49. F. Shirini, M. Abedini, R. Pourhasan-Kisomi, Chin. Chem. Lett. 25, 111 (2014)

    Article  CAS  Google Scholar 

  50. Y.-L. Wang, J. Luo, H.-Z. Zhi, Chem. Res. Chin. Univ. 29, 879 (2013)

    Article  CAS  Google Scholar 

  51. N.A. Liberto, S.P. Silva, A. de Fatima, S.A. Fernandes, Tetrahedron 69, 8245 (2013)

    Article  CAS  Google Scholar 

  52. A. Pourjavadi, S.H. Hosseini, R. Soleyman, J. Mol. Catal. A: Chem. 365, 55 (2012)

    Article  CAS  Google Scholar 

  53. U.K. Sharma, N. Sharma, R. Kumar, A.K. Sinha, Amino Acids 44, 1031 (2013)

    Article  CAS  Google Scholar 

  54. S. Khaksar, S.M. Vahdat, R. Najafi Moghaddamnejad, Monatshefte für Chem. 143, 1671 (2012)

    Article  CAS  Google Scholar 

  55. K. Konkala, N.M. Sabbavarapu, R. Katla, N.Y.V. Durga, T.V.K. Reddy, B.L.A.P. Devi, R.B.N. Prasad, Tetrahedron Lett. 53, 1968 (2012)

    Article  CAS  Google Scholar 

  56. M. Mirzai, H. Valizadeh, Synth. Commun. 42, 1268 (2012)

    Article  CAS  Google Scholar 

  57. S.V. Rashmi, N.C. Sandhya, B. Raghava, M.N. Kumara, K. Mantelingu, K.S. Rangappa, Synth. Commun. 42, 424 (2012)

    Article  CAS  Google Scholar 

  58. M. Moghadds, A. Davoodnia, M.M. Heravi, N. Chin, J. Catal. 33, 706 (2012)

    Google Scholar 

  59. A. de Vasconcelos, P.S. Oliveira, M. Ritter, R.A. Freitag, R.L. Romano, F.H. Quina, L. Pizzuti, C.M.P. Pereira, F.M. Stefanello, A.G. Barschak, J. Biochem. Mol. Toxicol. 26, 155 (2012)

    Article  Google Scholar 

  60. A. Ghorbani-Choghamarani, T. Taghipour, G. Azadi, J. Chin. Chem. Soc. 60, 1202 (2013)

    CAS  Google Scholar 

  61. E.N. Ostapchuk, A.S. Plaskon, O.O. Grygorenko, A.A. Tolmachev, S.V. Ryabukhin, J. Heterocycl. Chem. 50, 1299 (2013)

    Article  CAS  Google Scholar 

  62. B.S. Kuarm, J.V. Madhav, S.V. Laxmi, D.B. Rajitha, Synth. Commun. 42, 1211 (2012)

    Article  CAS  Google Scholar 

  63. H.R. Shaterian, M. Aghakhanizadeh, Phosphorus Sulfur Silicon Relat. Elem. 188, 1064 (2013)

    Article  CAS  Google Scholar 

  64. F. Heidarizadeh, E. Rezaee Nezhada, S. Sajjadifar, Sci. Iran. 20, 561 (2013)

    CAS  Google Scholar 

  65. S. Sajjadifar, E. Rezaee Nezhad, G. Darvishi, J. Chem. 2013, Article ID 834656, 6 pages, doi:10.1155/2013/834656

  66. A.N. Dadhania, V.K. Patel, D.K. Raval, J. Chem. Sci. 124, 921 (2012)

    Article  CAS  Google Scholar 

  67. F. Nemati, S.G. Alizadeh, J. Chem. 2013 (2013), Article ID 235818, 5 pages

  68. M.V. Yadav, S.V. Kuberkar, F.G. Khan, S.R. Khapate, A.D. Sagar, J. Chem. Pharm. Res. 5, 266 (2013)

    CAS  Google Scholar 

  69. N. Azizi, S. Dezfuli, M.M. Hahsemi, The Scientific World Journal, 2012 (2012) Article ID 908702, doi:10.1100/2012/908702

  70. D. An, Y.-S. Fan, Y. Gao, Z.-Q. Zhu, L.-Y. Zheng, S.-Q. Zhang, Eur. J. Org. Chem. 2014, 301 (2014)

    Article  CAS  Google Scholar 

  71. S.R. Jetti, D. Verma, S. Jain, Arab. J. Chem. (2013), in press, doi:10.1016/j.arabjc.2013.12.012

  72. P. Karthikeyan, S.S. Kumar, A.S. Arunrao, M.P. Narayan, P.R. Bhagat, Res. Chem. Intermed. 39, 1335 (2013)

    Article  CAS  Google Scholar 

  73. Y. Moussaoui, R. Ben Salem, J. Heterocycl. Chem. 50, 1209 (2013)

  74. Z. Xu, Y. Jiang, S. Zoua, Y. Liu, Phosphorus, Sulfur, and Silicon. Relat. Elem. 189, 791 (2014)

    Article  CAS  Google Scholar 

  75. Q. Liu, N. Pan, J. Xu, W. Zhang, F. Kong, Synth. Commun. 43, 139 (2013)

    Article  CAS  Google Scholar 

  76. X.-L. Shi, H. Yang, M. Tao, W. Zhang, RSC Adv. 3, 3939 (2013)

    Article  CAS  Google Scholar 

  77. Q. Zhang, X. Wang, Z. Li, W. Wu, J. Liu, H. Wu, S. Cui, K. Guo, RSC Adv. 4, 19710 (2014)

    Article  CAS  Google Scholar 

  78. P.I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 43, 5138 (2004)

    Article  CAS  Google Scholar 

  79. P.I. Dalko, Enantioselective organocatalysis: Reactions and experimental procedures (Wiley-VCH, Weinheim, 2007)

    Book  Google Scholar 

  80. A. Dondoni, A. Massi, Angew. Chem. Int. Ed. 47, 4638 (2008)

    Article  CAS  Google Scholar 

  81. C. Zhong, X. Shi, Eur. J. Org. Chem. 2010, 2999 (2010)

    Article  Google Scholar 

  82. A. Khazaei, M.A. Zolfigol, M. Mokhlesi, M. Pirveysian, Can. J. Chem. 90, 427 (2012)

    Article  CAS  Google Scholar 

  83. S. Verma, S.L. Jain, B. Sain, Tetrahedron Lett. 51, 6897 (2010)

    Article  CAS  Google Scholar 

  84. P.G. Cozzi, Y. Hayashi, Chem. Cat. Chem. 4, 887 (2012)

    CAS  Google Scholar 

  85. J.O. Metzger, Angew. Chem. Int. Ed. 37, 2975 (1998)

    Article  CAS  Google Scholar 

  86. K. Tanaka, F. Toda, Chem. Rev. 100, 1025 (2000)

    Article  CAS  Google Scholar 

  87. H. Kiyani, M. Ghiasi, Chin. Chem. Lett. 25, 313 (2014)

    Article  CAS  Google Scholar 

  88. H. Kiyani, M. Ghiasi, Res. Chem. Intermed. (2014), in press, doi:10.1007/s11164-014-1621-x

  89. K. Akbari Dilmaghani, B. Zeynizadeh, M. Amirpoor, Phosphorus Sulfur Silicon Relat. Elem. 188, 1634 (2013)

    Article  Google Scholar 

  90. A. Farhadi, M.A. Takassi, L. Hejazi, Z. Naturforsch. 68B, 51 (2013)

    Google Scholar 

  91. L.-Q. Kang, D.-Y. Jin, Y.-Q. Cai, Synth. Commun. 43, 1896 (2013)

    Article  CAS  Google Scholar 

  92. A. Kuraitheerthakumaran, S. Pazhamalai, M. Gopalakrishnan, Arab. J. Chem. (2011), in press, doi:10.1016/j.arabjc.2011.06.005

  93. S. Sayyahi, S. Jahanbakhshi, Z. Dehghani, J. Chem. 2013 (2013), Article ID 605324, doi:10.1155/2013/605324

Download references

Acknowledgments

The authors are thankful to Damghan University Research Council for partial support of this work.

Author information

Authors and Affiliations

  1. School of Chemistry, Damghan University, 36715-364, Damghan, Iran

    Hamzeh Kiyani & Maryam Ghiasi

Authors
  1. Hamzeh Kiyani
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Maryam Ghiasi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hamzeh Kiyani.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 233 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kiyani, H., Ghiasi, M. Phthalimide-N-sulfonic acid: a new and efficient organocatalyst for the Biginelli reaction under solvent-free conditions. Res Chem Intermed 41, 6635–6648 (2015). https://doi.org/10.1007/s11164-014-1766-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-014-1766-7

Keywords

Search

Navigation