Skip to main content

Advertisement

SpringerLink
Log in

Supported palladium oxide nanoparticles in Al-SBA-15 as an efficient and reusable catalyst for the synthesis of pyranopyrazole and benzylpyrazolyl coumarin derivatives via multicomponent reactions

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

Abstract

An eco-friendly method for diversity-oriented synthesis of substituted dihydropyrano[2,3-c]pyrazole and benzylpyrazolyl coumarin derivatives has been achieved via one-pot and multicomponent reaction in the presence of PdO/Al-SBA-15 as an efficient and recyclable catalyst in H2O/EtOH under reflux conditions. The significant merits of this method are wide scope, high yields of the desired products, short reaction times and simple workup procedure. In addition, this nanocatalyst was simply recovered and reused five times without significant loss in catalytic activity and also performance.

Graphical abstract

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

Fig. 1
Fig. 2
Scheme 1
Fig. 3
Fig. 4
Scheme 2
Scheme 3
Scheme 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)

    Article  Google Scholar 

  2. C.O. Kappe, Multicomponent Reactions (Wiley-VCH, Weinheim, 2005)

    Google Scholar 

  3. A.V. Stachulski, N.G. Berry, A. Lilian Low, S.L. Moores, E. Row, D.C. Warhurst, I.S. Adagu, J.-F. Rossignol, J. Med. Chem. 49, 1450 (2006)

    Article  CAS  PubMed  Google Scholar 

  4. W. Sun, L.D. Cama, E.T. Birzin, S. Warrier, L. Locco, R. Mosley, M.L. Hammond, S.P. Rohrer, Bioorg. Med. Chem. Lett. 16, 1468 (2006)

    Article  CAS  PubMed  Google Scholar 

  5. M.N. Elinson, A.S. Dorofeev, S.K. Feducovich, S.V. Gorbunov, R.F. Nasybullin, N.O. Stepanov, G.I. Nikishin, Tetrahedron Lett. 47, 7629 (2006)

    Article  CAS  Google Scholar 

  6. G.R. Geen, J.M. Evans, A.K. Vong, A. Katritzky, C. Rees, E. Scriven, Compr. Heterocycl. Chem. II 5, 469 (1996)

    CAS  Google Scholar 

  7. J. Wang, O. Novaro, X. Bokhimi, T. Lopez, R. Gomez, J. Navarrete, M. Llanos, E. Lopez-Salinas, J. Phys. Chem. B 101, 7448 (1997)

    Article  CAS  Google Scholar 

  8. M.J. Genin, C. Biles, B.J. Keiser, S.M. Poppe, S.M. Swaney, W.G. Tarpley, Y. Yagi, D.L. Romero, J. Med. Chem. 43, 1034 (2000)

    Article  CAS  PubMed  Google Scholar 

  9. S. Chobe, G. Mandawad, O. Yemul, S. Kinkar, B. Dawane, Int. J. Chemtech Res. 3, 938 (2011)

    CAS  Google Scholar 

  10. A. Akbari, B.F. Mirjalili, Rev. Roum. Chim. 61, 119 (2016)

    Google Scholar 

  11. Z. Wu, S. Wu, Y. Ye, X. Zhou, P. Wang, W. Xue, D. Hu, J. Heterocycl. Chem. 54, 325 (2017)

    Article  CAS  Google Scholar 

  12. A.A. Bekhit, A.M. Hassan, H.A. Abd El Razik, M.M. El-Miligy, E.J. El-Agroudy, A.E.-D.A. Bekhit, Eur. J. Med. Chem. 94, 30 (2015)

    Article  CAS  PubMed  Google Scholar 

  13. M. Kidwai, S. Saxena, M.K.R. Khan, S.S. Thukral, Bioorg. Med. Chem. Lett. 15, 4295 (2005)

    Article  CAS  PubMed  Google Scholar 

  14. S.R. Mandha, S. Siliveri, M. Alla, V.R. Bommena, M.R. Bommineni, S. Balasubramanian, Bioorg. Med. Chem. Lett. 22, 5272 (2012)

    Article  CAS  PubMed  Google Scholar 

  15. S.A. Patil, J. Wang, X.S. Li, J. Chen, T.S. Jones, A. Hosni-Ahmed, R. Patil, W.L. Seibel, W. Li, D.D. Miller, Bioorg. Med. Chem. Lett. 22, 4458 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. K.C. Nicolaou, S.A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem. Int. Ed. 41, 1668 (2002)

    Article  CAS  Google Scholar 

  17. J.-L. Wang, D. Liu, Z.-J. Zhang, S. Shan, X. Han, S.M. Srinivasula, C.M. Croce, E.S. Alnemri, Z. Huang, Proc. Natl. Acad. Sci. USA 97, 7124 (2000)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. E.-S. El-Tamany, F. El-Shahed, B. Mohamed, J. Serbian Chem. Soc. 64, 9 (1999)

    CAS  Google Scholar 

  19. M.E. Zaki, H.A. Soliman, O.A. Hiekal, A.E. Rashad, Naturforsch. C: Biosci. 61, 1 (2006)

    Article  CAS  Google Scholar 

  20. N.A.A. Latif, R.Z. Batran, M.A. Khedr, M.M. Abdalla, Bioorg. Chem. 67, 116 (2016)

    Article  PubMed  Google Scholar 

  21. P.P. Ghosh, G. Pal, S. Paul, A.R. Das, Green Chem. 14, 2691 (2012)

    Article  CAS  Google Scholar 

  22. B.H. Lee, M.F. Clothier, F.E. Dutton, G.A. Conder, S.S. Johnson, Bioorg. Med. Chem. Lett. 8, 3317 (1998)

    Article  CAS  PubMed  Google Scholar 

  23. J.-C. Jung, Y.-J. Jung, O.-S. Park, Synth. Commun. 31, 1195 (2001)

    Article  CAS  Google Scholar 

  24. S. Hesse, G. Kirsch, Tetrahedron Lett. 43, 1213 (2002)

    Article  CAS  Google Scholar 

  25. G. Melagraki, A. Afantitis, O. Igglessi-Markopoulou, A. Detsi, M. Koufaki, C. Kontogiorgis, D.J. Hadjipavlou-Litina, Eur. J. Med. Chem. 44, 3020 (2009)

    Article  CAS  PubMed  Google Scholar 

  26. C. Kresge, M. Leonowicz, W.J. Roth, J. Vartuli, J. Beck, Nature 359, 710 (1992)

    Article  CAS  Google Scholar 

  27. H. García, Pure Appl. Chem. 75, 1085 (2003)

    Article  Google Scholar 

  28. A. Bordoloi, Y. Hwang, J.-S. Hwang, S. Halligudi, Catal. Commun. 10, 1398 (2009)

    Article  CAS  Google Scholar 

  29. S. Alavi, H. Hosseini-Monfared, M. Siczek, J. Mol. Catal. A: Chem. 377, 16 (2013)

    Article  CAS  Google Scholar 

  30. A. Gedeon, A. Lassoued, J. Bonardet, J. Fraissard, Microporous Mesoporous Mater. 44, 801 (2001)

    Article  Google Scholar 

  31. M.D. Gracia, A.M. Balu, J.M. Campelo, R. Luque, J.M. Marinas, A.A. Romero, Appl. Catal. A 371, 85 (2009)

    Article  CAS  Google Scholar 

  32. Y.-S. Ooi, R. Zakaria, A.R. Mohamed, S. Bhatia, Catal. Comm. 5, 441 (2004)

    Article  CAS  Google Scholar 

  33. A. Vinu, D.P. Sawant, K. Ariga, M. Hartmann, S. Halligudi, Microporous Mesoporous Mater. 80, 195 (2005)

    Article  CAS  Google Scholar 

  34. R.J. White, R. Luque, V.L. Budarin, J.H. Clark, D.J. Macquarrie, Chem. Soc. Rev. 38, 481 (2009)

    Article  CAS  PubMed  Google Scholar 

  35. R. Tayebee, M.M. Amini, S. Pouyamanesh, A. Aliakbari, Dalton Trans. 44, 5888 (2015)

    Article  CAS  PubMed  Google Scholar 

  36. M. Durai, S. Kumaravel, A. Mukannan, B. Krishnakumar, S. Thiripuranthagan, Y.-H. Ahn, J. Porous Mater. 28, 1907 (2021)

    Article  Google Scholar 

  37. T. Klimova, J. Reyes, O. Gutiérrez, L. Lizama, Appl. Catal. A-Gen. 335, 159 (2008)

    Article  CAS  Google Scholar 

  38. X. Zhang, H. Dong, Y. Wang, N. Liu, Y. Zuo, L. Cui, Chem. Eng. J. 283, 1097 (2016)

    Article  CAS  Google Scholar 

  39. S.R. Thawarkar, N.D. Khupse, A. Kumar, ChemistrySelect 2, 6833 (2017)

    Article  CAS  Google Scholar 

  40. J. Long, K. Shen, L. Chen, Y. Li, J. Mater. Chem. A 4, 10254 (2016)

    Article  CAS  Google Scholar 

  41. T. Sahlabji, M. Abboud, R. Bel-Hadj-Tahar, M.S. Hamdy, J Nanopart Res 22, 1 (2020)

    Article  Google Scholar 

  42. A. Tăbăcaru, B. Furdui, I.O. Ghinea, G. Carac, R.M. Dinică, Inorg. Chim. Acta 455, 329 (2017)

    Article  Google Scholar 

  43. K. Zhou, J. Si, J. Jia, J. Huang, J. Zhou, G. Luo, F. Wei, RSC Adv. 4, 7766 (2014)

    Article  CAS  Google Scholar 

  44. A. Maleki, J. Rahimi, J. Porous Mater. 25, 1789 (2018)

    Article  CAS  Google Scholar 

  45. A. Maleki, M. Niksefat, J. Rahimi, R. Taheri-Ledari, Mater. Today Chem. 13, 110 (2019)

    Article  CAS  Google Scholar 

  46. V.B. Saptal, M.V. Saptal, R.S. Mane, T. Sasaki, B.M. Bhanage, ACS Omega 4, 643 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  47. J.S. Yadav, B.V.S. Reddy, P. Sridhar, J.S.S. Reddy, K. Nagaiah, N. Lingaiah, P.S. Saiprasad, Eur. J. Org 2004, 552 (2004)

    Article  Google Scholar 

  48. G.M. Ziarani, M. Rahimifard, F. Nouri, A. Badiei, J. Serb. Chem. Soc. 80, 1265 (2015)

    Article  CAS  Google Scholar 

  49. S. Sadjadi, M.M. Heravi, V. Zadsirjan, V. Farzaneh, Res. Chem. Intermed. 44, 6765 (2018)

    Article  CAS  Google Scholar 

  50. B.B.F. Mirjalili, A. Bamoniri, L. Asadollah Salmanpoor, J. Nanostruct. 8, 276 (2018)

    CAS  Google Scholar 

  51. H.A. Oskooie, M.M. Heravi, N. Karimi, H. Hamidi, Synth. Commun. 41, 3344 (2011)

    Article  CAS  Google Scholar 

  52. S.D. Dindulkar, P. Parthiban, Y.T. Jeong, Monatsh. Chem. 143, 113 (2012)

    Article  CAS  Google Scholar 

  53. M.C. Pirrung, K.D. Sarma, J. Am. Chem. Soc. 126, 444 (2004)

    Article  CAS  PubMed  Google Scholar 

  54. R.N. Butler, A.G. Coyne, Chem. Rev. 110, 6302 (2010)

    Article  CAS  PubMed  Google Scholar 

  55. M.-O. Simon, C.-J. Li, Chem. Soc. Rev. 41, 1415 (2012)

    Article  CAS  PubMed  Google Scholar 

  56. Y. Jung, R. Marcus, J. Am. Chem. Soc. 129, 5492 (2007)

    Article  CAS  PubMed  Google Scholar 

  57. A. Lubineau, J. Augé, Water as Solvent in Organic Synthesis (Springer, Berlin/Heidelberg, 1999)

    Book  Google Scholar 

  58. M. Van Leeuwen, Fluid Phase Equilib. 99, 1 (1994)

    Article  Google Scholar 

  59. G. Akerlof, J. Am. Chem. Soc. 54, 4125 (1932)

    Article  CAS  Google Scholar 

  60. S.M. Mejía, E. Flórez, F. Mondragón, J. Chem. Phys. 136, 144306 (2012)

    Article  PubMed  Google Scholar 

  61. R.A. Sheldon, Curr. Opin. Green Sustain. Chem. 18, 13 (2019)

    Article  Google Scholar 

  62. M. Mamaghani, R.H. Nia, F. Shirini, K. Tabatabaeian, M. Rassa, Med. Chem. Res. 24, 1916 (2015)

    Article  CAS  Google Scholar 

  63. A.R. Moosavi-Zare, M.A. Zolfigol, R. Salehi-Moratab, E. Noroozizadeh, J. Mol. Catal. A Chem. 415, 144 (2016)

    Article  CAS  Google Scholar 

  64. G. Vasuki, K. Kumaravel, Tetrahedron Lett. 49, 5636 (2008)

    Article  CAS  Google Scholar 

  65. Y.M. Litvinov, A.A. Shestopalov, L.A. Rodinovskaya, A.M. Shestopalov, J. Comb. Chem. 11, 914 (2009)

    Article  CAS  PubMed  Google Scholar 

  66. M. Wu, Q. Feng, D. Wan, J. Ma, Synth. Commun. 43, 1721 (2013)

    Article  CAS  Google Scholar 

  67. B.M. Chougala, S. Samundeeswari, M. Holiyachi, L.A. Shastri, S. Dodamani, S. Jalalpure, S.R. Dixit, S.D. Joshi, V.A. Sunagar, Eur. J. Med. Chem. 125, 101 (2017)

    Article  CAS  PubMed  Google Scholar 

  68. M.M. Reddy, V. Jayashankara, M. Pasha, Synth. Commun. 40, 2930 (2010)

    Article  CAS  Google Scholar 

  69. A. Siddekha, A. Nizam, M. Pasha, Spectrochim. Acta A Mol. Biomol. Spectrosc. 81, 431 (2011)

    Article  CAS  PubMed  Google Scholar 

  70. R.-Y. Guo, Z.-M. An, L.-P. Mo, S.-T. Yang, H.-X. Liu, S.-X. Wang, Z.-H. Zhang, Tetrahedron 69, 9931 (2013)

    Article  CAS  Google Scholar 

  71. M. Kangani, N. Hazeri, M.T. Maghsoodlou, K. Khandan-Barani, M. Kheyrollahi, F. Nezhadshahrokhabadi, J. Iran. Chem. Soc. 12, 47 (2015)

    Article  CAS  Google Scholar 

  72. A.R. Moosavi-Zare, M.A. Zolfigol, A. Mousavi-Tashar, Res. Chem. Intermed. 42, 7305 (2016)

    Article  CAS  Google Scholar 

  73. S.Y. Ebrahimipour, Z.R. Ranjabr, E.T. Kermani, B.P. Amiri, H.A. Rudbari, A. Saccá, F. Hoseinzade, Transit. Met. Chem. 40, 39 (2015)

    Article  CAS  Google Scholar 

  74. M. Bihani, P.P. Bora, G. Bez, H. Askari, ACS Sustain. Chem. Eng. 1, 440 (2013)

    Article  CAS  Google Scholar 

  75. M. Babaie, H. Sheibani, Arab. J. Chem. 4, 159 (2011)

    Article  CAS  Google Scholar 

  76. M. Abdollahi-Alibeik, A. Moaddeli, K. Masoomi, RSC Adv. 5, 74932 (2015)

    Article  CAS  Google Scholar 

  77. M. Heravi, N. Ghobadi, Sci. Iranica C 22, 911 (2015)

    Google Scholar 

  78. M.M. Heravi, S. Sadjadi, Tetrahedron 65, 7761 (2009)

    Article  CAS  Google Scholar 

  79. M.M. Heravi, B. Talaei, Adv. Heterocycl. Chem. 122, 43 (2017)

    Article  CAS  Google Scholar 

  80. S. Sadjadi, M.M. Heravi, N. Nazari, RSC Adv. 6, 53203 (2016)

    Article  CAS  Google Scholar 

  81. M.M. Heravi, V. Zadsirjan, K. Kafshdarzadeh, Z. Amiri, Asian J. Org. Chem. 9, 1999 (2020)

    Article  CAS  Google Scholar 

  82. M.M. Heravi, R. Moradi, M. Malmir, Curr. Org. Chem. 22, 165 (2018)

    Article  CAS  Google Scholar 

  83. A. Rezvanian, V. Zadsirjan, P. Saedi, M.M. Heravi, J. Heterocycl. Chem. 55, 2772 (2018)

    Article  CAS  Google Scholar 

  84. M. Saeedi, M.M. Heravi, Y.S. Beheshtiha, H.A. Oskooie, Tetrahedron 66, 5345 (2010)

    Article  CAS  Google Scholar 

  85. M.M. Heravi, E. Hashemi, Y.S. Beheshtiha, S. Ahmadi, T. Hosseinnejad, J. Mol. Catal. A Chem. 394, 74 (2014)

    Article  CAS  Google Scholar 

  86. H. Atashin, R. Malakooti, J. Chin. Chem. Soc. 61, 1039 (2014)

    Article  CAS  Google Scholar 

  87. Z.Y. Wu, H.J. Wang, T.T. Zhuang, L.B. Sun, Y.M. Wang, J.H. Zhu, Adv. Funct. Mater. 18, 82 (2008)

    Article  CAS  Google Scholar 

  88. Z. Wang, J. Ren, Z. Li, Synth. Commun. 30, 763 (2000)

    Article  CAS  Google Scholar 

  89. S. Zhou, J. Ren, M. Liu, L. Ren, Y. Liu, P. Gong, Bioorg. Chem. 57, 30 (2014)

    Article  CAS  PubMed  Google Scholar 

  90. H.R. Shaterian, M. Kangani, Res. Chem. Intermed. 40, 1997 (2014)

    Article  CAS  Google Scholar 

  91. A. Ahad, M. Farooqui, Res. Chem. Intermed. 43, 2445 (2017)

    Article  CAS  Google Scholar 

  92. H. Kiyani, M. Bamdad, Res. Chem. Intermed. 44, 2761 (2018)

    Article  CAS  Google Scholar 

  93. G.M. Reddy, G. Sravya, G. Yuvaraja, A. Camilo, G.V. Zyryanov, J.R. Garcia, Res. Chem. Intermed. 44, 7491 (2018)

    Article  CAS  Google Scholar 

  94. F. Mohamadpour, J Chem Sci 132, 1 (2020)

    Article  Google Scholar 

  95. P. Sinija, K. Sreekumar, RSC Adv. 5, 101776 (2015)

    Article  CAS  Google Scholar 

  96. J. Safaei-Ghomi, H. Shahbazi-Alavi, E. Heidari-Baghbahadorani, J. Chem. Res. 39, 410 (2015)

    Article  CAS  Google Scholar 

  97. M. Bakherad, A. Keivanloo, M. Gholizadeh, R. Doosti, M. Javanmardi, Res. Chem. Intermed. 43, 1013 (2017)

    Article  CAS  Google Scholar 

  98. A. Maleki, V. Eskandarpour, J. Iran. Chem. Soc. 16, 1459 (2019)

    Article  CAS  Google Scholar 

  99. S. Paul, K. Pradhan, S. Ghosh, S. De, A.R. Das, Tetrahedron 70, 6088 (2014)

    Article  CAS  Google Scholar 

  100. M. Beerappa, K. Shivashankar, Synth. Commun. 48, 146 (2018)

    Article  CAS  Google Scholar 

  101. M. Murahari, V. Mahajan, S. Neeladri, M.S. Kumar, Y. Mayur, Bioorg. Chem. 86, 583 (2019)

    Article  CAS  PubMed  Google Scholar 

  102. D. Azarifar, S.-M. Khatami, M.A. Zolfigol, R. Nejat-Yami, J. Iran. Chem. Soc. 11, 1223 (2014)

    Article  CAS  Google Scholar 

  103. L. Sharanina, V. Promonenkov, V. Marshtupa, A. Pashchenko, V. Puzanova, Y.A. Sharanin, N. Klyuev, L. Gusev, A. Gnatusina, Chem. Heterocycl. Compd. 18, 607 (1982)

    Article  Google Scholar 

  104. S. Nagaraju, B. Paplal, K. Sathish, S. Giri, D. Kashinath, Tetrahedron Lett. 58, 4200 (2017)

    Article  CAS  Google Scholar 

  105. C. Mao, J. Zheng, B.M. Matsagar, R.K. Kankala, T. Ahamad, Y. Yang, K.C.W. Wu, X. Zhang, Catal. Sci. Technol. 10, 2443 (2020)

    Article  CAS  Google Scholar 

  106. J. Gujar, M. Chaudhari, D. Kawade, M. Shingare, Tetrahedron Lett. 55, 6030 (2014)

    Article  CAS  Google Scholar 

  107. H. Veisi, A.A. Manesh, N. Khankhani, R. Ghorbani-Vaghei, RSC Adv. 4, 25057 (2014)

    Article  CAS  Google Scholar 

  108. S.H.S. Azzam, M. Pasha, Tetrahedron Lett. 53, 6834 (2012)

    Article  CAS  Google Scholar 

  109. A. Saha, S. Payra, S. Banerjee, Green Chem. 17, 2859 (2015)

    Article  CAS  Google Scholar 

  110. Z. Piruzmand, J. Safaei-Ghomi, M. Ghasemzadeh, Med Chem. 9, 10 (2016)

    Google Scholar 

  111. H. Jelali, A. Chakchouk-Mtibaa, L. Baklouti, H. Bilel, Y. Bathich, L. Mellouli, N. Hamdi, J. Chem. 2019, 1 (2019)

    Article  Google Scholar 

  112. K.S. Dalal, Y.A. Tayade, Y.B. Wagh, D.R. Trivedi, D.S. Dalal, B.L. Chaudhari, RSC Adv. 6, 14868 (2016)

    Article  CAS  Google Scholar 

  113. H.R. Safaei, M. Shekouhy, A. Shirinfeshan, S. Rahmanpur, Mol. Divers. 16, 669 (2012)

    Article  CAS  PubMed  Google Scholar 

  114. M.G. Dehbalaei, N. Foroughifar, H. Pasdar, A. Khajeh-Amiri, N. Foroughifar, M. Alikarami, Res. Chem. Intermed. 43, 3035 (2017)

    Article  CAS  Google Scholar 

  115. Y. Zou, Y. Hu, H. Liu, D.Q. Shi, J. Heterocycl. Chem. 50, 1174 (2013)

    CAS  Google Scholar 

  116. M.M. Ramiz, I.S.A. Hafiz, M.A.A. Reheim, H.M. Gaber, J. Chin. Chem. Soc. 59, 72 (2012)

    Article  CAS  Google Scholar 

  117. H.V. Chavan, S.B. Babar, R.U. Hoval, B.P. Bandgar, Bull. Korean Chem. Soc. 32, 3963 (2011)

    Article  CAS  Google Scholar 

  118. J. Ebrahimi, A. Mohammadi, V. Pakjoo, E. Bahramzade, A. Habibi, J. Chem. Sci. 124, 1013 (2012)

    Article  CAS  Google Scholar 

  119. S. Maddila, S. Gorle, S. Shabalala, O. Oyetade, S.N. Maddila, P. Lavanya, S.B. Jonnalagadda, Arab. J. Chem. 12, 671 (2019)

    Article  CAS  Google Scholar 

  120. A. Javid, A. Khojastehnezhad, H. Eshghi, F. Moeinpour, F.F. Bamoharram, J. Ebrahimi, Org. Prep. Proced. Int. 48, 377 (2016)

    Article  CAS  Google Scholar 

  121. G.M. Reddy, J. Raul Garcia, J. Heterocycl. Chem. 54, 89 (2017)

    Article  CAS  Google Scholar 

  122. Y.A. Tayade, S.A. Padvi, Y.B. Wagh, D.S. Dalal, Tetrahedron Lett. 56, 2441 (2015)

    Article  CAS  Google Scholar 

  123. A.S. Waghmare, S.S. Pandit, J. Saudi Chem. Soc. 21, 286 (2017)

    Article  CAS  Google Scholar 

  124. C.-F. Zhou, J.-J. Li, W.-K. Su, Chin. Chem. Lett. 27, 1686 (2016)

    Article  CAS  Google Scholar 

  125. M. Fatahpour, F.N. Sadeh, N. Hazeri, M.T. Maghsoodlou, M. Lashkari, J. Iran. Chem. Soc. 14, 1945 (2017)

    Article  CAS  Google Scholar 

  126. M.A. Chaudhari, J.B. Gujar, D.S. Kawade, N.R. Jogdand, M.S. Shingare, Cogent Chem. 1, 1063830 (2015)

    Article  Google Scholar 

  127. M. Zakeri, M.M. Nasef, T. Kargaran, A. Ahmad, E. Abouzari-Lotf, J. Asadi, Res. Chem. Intermed. 43, 717 (2017)

    Article  CAS  Google Scholar 

  128. M.A.E.A.A. Ali, Tetrahedron 70, 2971 (2014)

    Article  Google Scholar 

  129. H.R. Shaterian, K. Azizi, Res. Chem. Intermed. 40, 661 (2014)

    Article  CAS  Google Scholar 

  130. F. Moeinpour, A. Khojastehnezhad, Chin. Chem. Lett. 26, 575 (2015)

    Article  CAS  Google Scholar 

  131. S. Yadav, J.M. Khurana, Chin. J. Catal. 36, 1042 (2015)

    Article  CAS  Google Scholar 

  132. E. Soleimani, M. Jafarzadeh, P. Norouzi, J. Dayou, C.S. Sipaut, R.F. Mansa, P. Saei, J. Chin. Chem. Soc. 62, 1155 (2015)

    Article  CAS  Google Scholar 

  133. K.G. Patel, N.M. Misra, R.H. Vekariya, R.R. Shettigar, Res. Chem. Intermed. 44, 289 (2018)

    Article  CAS  Google Scholar 

  134. M. Arghan, N. Koukabi, E. Kolvari, J. Saudi Chem. Soc. 23, 150 (2019)

    Article  CAS  Google Scholar 

  135. Z. Hajizadeh, A. Maleki, Mol. Catal. 460, 87 (2018)

    Article  CAS  Google Scholar 

  136. A.S. Nagarajan, B.S. Reddy, Synlett 2009, 2002 (2009)

    Article  Google Scholar 

  137. A.M. Zonouz, I. Eskandari, H.R. Khavasi, Tetrahedron Lett. 53, 5519 (2012)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors appreciate partial financial supports from Alzahra University. M.M.H. is also thankful to Iran National Science Foundation (INSF) for the individual given grant. R.M. is thankful to University of Birjand for the partial founding of this study.

Author information

Authors and Affiliations

  1. Department of Chemistry, School of Physics and Chemistry, Alzahra University, Vanak, Tehran, Iran

    Majid M. Heravi, Kosar Kafshdarzadeh, Zahra Amiri & Vahideh Zadsirjan

  2. Nanochemistry Research Laboratory, Department of Chemistry, University of Birjand, P. O. Box: 97175-615, Birjand, Iran

    Reihaneh Malakooti & Hassan Atashin

Authors
  1. Majid M. Heravi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Reihaneh Malakooti
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kosar Kafshdarzadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zahra Amiri
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Vahideh Zadsirjan
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Hassan Atashin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Majid M. Heravi or Reihaneh Malakooti.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 17353 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Heravi, M.M., Malakooti, R., Kafshdarzadeh, K. et al. Supported palladium oxide nanoparticles in Al-SBA-15 as an efficient and reusable catalyst for the synthesis of pyranopyrazole and benzylpyrazolyl coumarin derivatives via multicomponent reactions. Res Chem Intermed 48, 203–234 (2022). https://doi.org/10.1007/s11164-021-04619-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-021-04619-z

Keywords

Search

Navigation