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Highly efficient and green synthesis of spiro[indoline-3,9′-xanthene]trione and spiro[chromene-4,3′-indoline]-3-carbonitrile derivatives in water catalyzed by graphene oxide-supported dicationic ionic liquid

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Abstract

In this article, a mild and highly efficacious synthetic route has been developed for the synthesis of spiro[indoline-3,9′-xanthene]trione and spiro[chromene-4,3′-indoline]-3-carbonitrile derivatives using graphene oxide-supported dicationic ionic liquid (DIL@GO) as a heterogeneous catalyst in aqueous media. Targeted spiro[indoline-3,9′-xanthene]trione derivatives were synthesized via one-pot condensation of substituted isatins and 1,3-diketone compounds (1,3-cyclohexanedione/dimedone), and spiro[chromene-4,3′-indoline]-3-carbonitrile derivatives were synthesized via one-pot reaction of substituted isatins, malononitrile, and enolizable C-H-activated compounds (2-hydroxynaphthalene-1,4-dione/dimedone). The DIL@GO catalyst demonstrated outstanding catalytic capabilities in all the tested reactions and yielded excellent isolated yields of the final products within a short reaction time. Additionally, the heterogeneous nature of the catalyst facilitates catalyst separation through centrifugation, and its reusability up to five successive reaction cycles with retention in activity makes this methodology more advantageous and environmentally benign.

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References

  1. K.U. Sadek, R.A.H. Mekheimer, M. Abd-Elmonem, A. Abdel-Hameed, M.H. Elnagdi, Tetrahedron Asymmetry 28, 1462 (2017)

    Article  CAS  Google Scholar 

  2. C.M. Meléndez Gómez, V.V. Kouznetsov, M.A. Sortino, S.L. Álvarez, S.A. Zacchino, Bioorganic Med. Chem. 16, 7908 (2008)

    Article  Google Scholar 

  3. G.S. Singh, Z.Y. Desta, Chem. Rev. 112, 6104 (2012)

    Article  CAS  PubMed  Google Scholar 

  4. A.E. Goetz, T.K. Shah, N.K. Garg, Chem. Commun. 51, 34 (2015)

    Article  CAS  Google Scholar 

  5. E. Vitaku, D.T. Smith, J.T. Njardarson, J. Med. Chem. 57, 10257 (2014)

    Article  CAS  PubMed  Google Scholar 

  6. Y. Zheng, C.M. Tice, S.B. Singh, Bioorganic Med Chem. Lett. 24, 3673 (2014)

    Article  CAS  Google Scholar 

  7. N. Martín, M. Dusselier, D.E. De Vos, F.G. Cirujano, ACS Catal. 9, 44 (2019)

    Article  Google Scholar 

  8. F.G. Cirujano, M. Stalpaert, D.E. De Vos, Green Chem. 20, 2481 (2018)

    Article  CAS  Google Scholar 

  9. T.L. Pavlovska, R.G. Redkin, V.V. Lipson, D.V. Atamanuk, Mol. Divers. 20, 299 (2016)

    Article  CAS  PubMed  Google Scholar 

  10. A. Guardia, J. Baiget, M. Cacho, A. Pérez, M. Ortega-Guerra, W. Nxumalo, S.D. Khanye, J. Rullas, F. Ortega, E. Jiménez, E. Pérez-Herrán, M.T. Fraile-Gabaldón, J. Esquivias, R. Fernández, E. Porras-De Francisco, L. Encinas, M. Alonso, I. Giordano, C. Rivero, J. Miguel-Siles, J.G. Osende, K.A. Badiola, P.J. Rutledge, M.H. Todd, M. Remuiñán, C. Alemparte, J. Med. Chem. 61, 11327 (2018)

    Article  CAS  PubMed  Google Scholar 

  11. G.A. Khan, G.A. Naikoo, J.A. War, I.A. Sheikh, U.J. Pandit, I. Khan, A.K. Harit, R. Das, J. Heterocycl. Chem. 55, 699 (2018)

    Article  CAS  Google Scholar 

  12. K. Nakao, K. Ikeda, T. Kurokawa, Y. Togashi, H. Umeuchi, T. Honda, K. Okano, H. Mochizuki, Jpn. J. Neuropsychopharmacol. 28, 75 (2008)

    CAS  Google Scholar 

  13. D.M. Reddy, N.A. Qazi, S.D. Sawant, A.H. Bandey, J. Srinivas, M. Shankar, S.K. Singh, M. Verma, G. Chashoo, A. Saxena, D. Mondhe, A.K. Saxena, V.K. Sethi, S.C. Taneja, G.N. Qazi, H.M. Sampath Kumar, Eur. J. Med. Chem. 46, 3210 (2011)

    Article  CAS  PubMed  Google Scholar 

  14. Z.-G. Ding, J.-Y. Zhao, M.-G. Li, R. Huang, Q.-M. Li, X.-L. Cui, H.-J. Zhu, M.-L. Wen, J. Nat. Prod. 75, 1994 (2012)

    Article  CAS  PubMed  Google Scholar 

  15. M.J. Pawar, A.B. Burungale, B.K. Karale, Arkivoc 2009, 97 (2009)

    Article  Google Scholar 

  16. S. Kesharwani, N.K. Sahu, D.V. Kohli, Pharm. Chem. J. 43, 315 (2009)

    Article  CAS  Google Scholar 

  17. S.S. Panda, R.A. Jones, P. Bachawala, P.P. Mohapatra, Mini-Reviews. Med. Chem. 17, 1515 (2017)

    CAS  Google Scholar 

  18. A. Gollner, D. Rudolph, H. Arnhof, M. Bauer, S.M. Blake, G. Boehmelt, X.L. Cockroft, G. Dahmann, P. Ettmayer, T. Gerstberger, J. Karolyi-Oezguer, D. Kessler, C. Kofink, J. Ramharter, J. Rinnenthal, A. Savchenko, R. Schnitzer, H. Weinstabl, U. Weyer-Czernilofsky, T. Wunberg, D.B. McConnell, J. Med. Chem. 59, 10147 (2016)

    Article  CAS  PubMed  Google Scholar 

  19. K. Ding, Y. Lu, Z. Nikolovska-Coleska, G. Wang, S. Qiu, S. Shangary, W. Gao, D. Qin, J. Stuckey, K. Krajewski, P.P. Roller, S. Wang, J. Med. Chem. 49, 3432 (2006)

    Article  CAS  PubMed  Google Scholar 

  20. N.V. Plechkova, K.R. Seddon, Chem. Soc. Rev. 37, 123 (2008)

    Article  CAS  PubMed  Google Scholar 

  21. P.R. Sebahar, R.M. Williams, J. Am. Chem. Soc. 122, 5666 (2000)

    Article  CAS  Google Scholar 

  22. E. García Prado, M.D. García Gimenez, R. De la Puerta Vázquez, J.L. Espartero Sánchez, M.T. Sáenz Rodríguez, Phytomedicine 14, 280 (2007)

    Article  PubMed  Google Scholar 

  23. T.H. Kang, K. Matsumoto, M. Tohda, Y. Murakami, H. Takayama, M. Kitajima, N. Aimi, H. Watanabe, Eur. J. Pharmacol. 444, 39 (2002)

    Article  CAS  PubMed  Google Scholar 

  24. A.S. Girgis, Eur. J. Med. Chem. 44, 91 (2009)

    Article  CAS  PubMed  Google Scholar 

  25. A. Amal Raj, R. Raghunathan, M.R. SrideviKumari, N. Raman, Bioorganic Med. Chem. 11, 407 (2003)

    Article  Google Scholar 

  26. B. Yu, D.Q. Yu, H.M. Liu, Eur. J. Med. Chem. 97, 673 (2015)

    Article  CAS  PubMed  Google Scholar 

  27. N.R. Ball-Jones, J.J. Badillo, A.K. Franz, Org. Biomol. Chem. 10, 5165 (2012)

    Article  CAS  PubMed  Google Scholar 

  28. Y.-T. Yang, J.-F. Zhu, G. Liao, H.-J. Xu, B. Yu, Curr. Med. Chem. 25, 2233 (2018)

    Article  CAS  PubMed  Google Scholar 

  29. S.A. Pogosyan, M.V. Pogosyan, L.R. Aleksanyan, A.S. Safaryan, A.G. Arakelyan, Russ. J. Org. Chem. 54, 1860 (2018)

    Article  CAS  Google Scholar 

  30. P. Nazari, A. Bazi, S.A. Ayatollahi, H. Dolati, S.M. Mahdavi, L. Rafighdoost, M. Amirmostofian, Iran. J. Pharm. Res. 16, 943 (2017)

    CAS  PubMed  PubMed Central  Google Scholar 

  31. A. Barmak, K. Niknam, G. Mohebbi, H. Pournabi, Microb. Pathog. 130, 95 (2019)

    Article  CAS  PubMed  Google Scholar 

  32. D.R. Chandam, A.A. Patravale, S.D. Jadhav, M.B. Deshmukh, J. Mol. Liq. 240, 98 (2017)

    Article  CAS  Google Scholar 

  33. G.M. Ziarani, N. Lashgari, A.R. Badiei, Sci. Iran. 20, 580 (2013)

    CAS  Google Scholar 

  34. M.S. Ghasemzadeh, B. Akhlaghinia, ChemistrySelect 3, 3161 (2018)

    Article  CAS  Google Scholar 

  35. J. Kothandapani, A. Ganesan, G.K. Mani, A.J. Kulandaisamy, J.B.B. Rayappan, S. Selva-Ganesan, Tetrahedron Lett. 57, 3472 (2016)

    Article  CAS  Google Scholar 

  36. M. Zhang, Q.-Y. Fu, G. Gao, H.-Y. He, Y. Zhang, Y.-S. Wu, Z.-H. Zhang, A.C.S. Sustain, Chem. Eng. 5, 6175 (2017)

    CAS  Google Scholar 

  37. A. Mobinikhaledi, N. Foroughifar, M.A.B. Fard, Synth. Commun. 41, 441 (2011)

    Article  CAS  Google Scholar 

  38. H.M. Meshram, D.A. Kumar, B.R.V. Prasad, P.R. Goud, Helv. Chim. Acta 93, 648 (2010)

    Article  CAS  Google Scholar 

  39. C. Chen, C. Lv, J. Liang, J. Jin, L. Wang, C. Wu, R. Shen, Molecules 22, 1295 (2017)

    Article  PubMed Central  Google Scholar 

  40. L.-Y. Xie, S. Peng, L.-H. Lu, J. Hu, W.-H. Bao, F. Zeng, Z. Tang, X. Xu, W.-M. He, ACS Sustain Chem. Eng. 6, 7989 (2018)

    Article  CAS  Google Scholar 

  41. C. Wu, L.-H. Lu, A.-Z. Peng, G.-K. Jia, C. Peng, Z. Cao, Z. Tang, W.-M. He, X. Xu, Green Chem. 20, 3683 (2018)

    Article  CAS  Google Scholar 

  42. T. Selvam, A. Machoke, W. Schwieger, Appl. Catal. A Gen. 445–446, 92 (2012)

    Article  Google Scholar 

  43. P. Kaur, H.K. Chopra, Curr. Org. Chem. 23, 2881 (2019)

    Article  CAS  Google Scholar 

  44. H.N. Dadhania, D.K. Raval, A.N. Dadhania, Catal Sci. Technol. 5, 4806 (2015)

    Article  CAS  Google Scholar 

  45. J.-F. Wei, J. Jiao, J.-J. Feng, J. Lv, X.-R. Zhang, X.-Y. Shi, Z.-G. Chen, J. Org. Chem. 74, 6283 (2009)

    Article  CAS  PubMed  Google Scholar 

  46. M. Ao, P. Huang, G. Xu, X. Yang, Y. Wang, Colloid Polym. Sci. 287, 395 (2009)

    Article  CAS  Google Scholar 

  47. T. Payagala, J. Huang, Z.S. Breitbach, P.S. Sharma, D.W. Armstrong, Chem. Mater. 19, 5848 (2007)

    Article  CAS  Google Scholar 

  48. A. Chinnappan, A.H. Jadhav, J.M.C. Puguan, R. Appiah-Ntiamoah, H. Kim, Energy 79, 482 (2015)

    Article  CAS  Google Scholar 

  49. Y.-C. Shi, S.-S. Chen, J.-J. Feng, X.-X. Lin, W. Wang, A.-J. Wang, Appl. Surf. Sci. 441, 438 (2018)

    Article  CAS  Google Scholar 

  50. A. Chinnappan, J.M.C. Puguan, W.-J. Chung, H. Kim, J. Power Sources 293, 429 (2015)

    Article  CAS  Google Scholar 

  51. C. Rizzo, F. D’Anna, S. Marullo, R. Noto, J. Org. Chem. 79, 8678 (2014)

    Article  CAS  PubMed  Google Scholar 

  52. X. Han, D.W. Armstrong, Org. Lett. 7, 4205 (2005)

    Article  CAS  PubMed  Google Scholar 

  53. H. Qiu, S. Jiang, X. Liu, L. Zhao, J. Chromatogr. A 1116, 46 (2006)

    Article  CAS  PubMed  Google Scholar 

  54. C. Yao, Y. Hou, W. Wu, S. Ren, H. Liu, Green Chem. 20, 3101 (2018)

    Article  CAS  Google Scholar 

  55. M. Qi, D.W. Armstrong, Anal. Bioanal. Chem. 388, 889 (2007)

    Article  CAS  PubMed  Google Scholar 

  56. A.H. Jadhav, A. Chinnappan, R.H. Patil, S.V. Kostjuk, H. Kim, Chem. Eng. J. 243, 92 (2014)

    Article  CAS  Google Scholar 

  57. A.H. Jadhav, H. Kim, Chem. Eng. J. 200–202, 264 (2012)

    Article  Google Scholar 

  58. J. Li, X.-Y. Shi, Y.-Y. Bi, J.-F. Wei, Z.-G. Chen, ACS Catal. 1, 657 (2011)

    Article  CAS  Google Scholar 

  59. B. Lai, R. Bai, Y. Gu, A.C.S. Sustain, Chem. Eng. 6, 17076 (2018)

    CAS  Google Scholar 

  60. V.H. Jadhav, J.G. Kim, H.J. Jeong, D.W. Kim, J. Org. Chem. 80, 7275 (2015)

    Article  CAS  PubMed  Google Scholar 

  61. A.H. Jadhav, K. Lee, S. Koo, J.G. Seo, RSC Adv. 5, 26197 (2015)

    Article  CAS  Google Scholar 

  62. D. Zhao, M. Liu, J. Zhang, J. Li, P. Ren, Chem. Eng. J. 221, 99 (2013)

    Article  CAS  Google Scholar 

  63. M. Hu, Z. Yao, X. Wang, Ind. Eng. Chem. Res. 56, 3477 (2017)

    Article  CAS  Google Scholar 

  64. S. Kumar, O.P. Khatri, S. Cordier, R. Boukherroub, S.L. Jain, Chem. A Eur. J. 21, 3488 (2015)

    Article  CAS  Google Scholar 

  65. Q. Zhao, C. Bai, W. Zhang, Y. Li, G. Zhang, F. Zhang, X. Fan, Ind. Eng. Chem. Res. 53, 4232 (2014)

    Article  CAS  Google Scholar 

  66. V. Georgakilas, M. Otyepka, A.B. Bourlinos, V. Chandra, N. Kim, K.C. Kemp, P. Hobza, R. Zboril, K.S. Kim, Chem. Rev. 112, 6156 (2012)

    Article  CAS  PubMed  Google Scholar 

  67. M.C. Hsiao, S.H. Liao, M.Y. Yen, P.I. Liu, N.W. Pu, C.A. Wang, C.C.M. Ma, ACS Appl. Mater. Interfaces 2, 3092 (2010)

    Article  CAS  PubMed  Google Scholar 

  68. D. Katheriya, N. Patel, H. Dadhania, and A. Dadhania, J. Iran. Chem. Soc. (2020).

  69. H. Dadhania, D. Raval, and A. Dadhania, Polycycl. Aromat. Compd. 1 (2019).

  70. N. Patel, D. Katheriya, H. Dadhania, A. Dadhania, Res. Chem. Intermed. 45, 5595 (2019)

    Article  CAS  Google Scholar 

  71. H.N. Dadhania, D.K. Raval, A.N. Dadhania, Res. Chem. Intermed. 44, 117 (2018)

    Article  CAS  Google Scholar 

  72. S. Ahadi, H.R. Khavasi, A. Bazgir, Chem. Pharm. Bull. (Tokyo). 56, 1328 (2008)

    Article  CAS  PubMed  Google Scholar 

  73. S.M. Mousavifar, H. Kefayati, S. Shariati, Appl. Organomet. Chem. 32, e4242 (2018)

    Article  Google Scholar 

  74. G. Shanthi, G. Subbulakshmi, P.T. Perumal, Tetrahedron 63, 2057 (2007)

    Article  CAS  Google Scholar 

  75. S.-L. Zhu, S.-J. Ji, Y. Zhang, Tetrahedron 63, 9365 (2007)

    Article  CAS  Google Scholar 

  76. L.M. Wang, N. Jiao, J. Qiu, J.J. Yu, J.Q. Liu, F. Lou Guo, Y. Liu, Tetrahedron 66, 339 (2010)

    Article  CAS  Google Scholar 

  77. B. Karmakar, A. Nayak, J. Banerji, Tetrahedron Lett. 53, 5004 (2012)

    Article  CAS  Google Scholar 

  78. B. Sadeghi, M. Ghasemi Pirbaluti, P. Farokhi Nezhad, R. Abbasi Nezhad, Res. Chem. Intermed. 41, 4047 (2015)

    Article  CAS  Google Scholar 

  79. J. Safaei-Ghomi, S.H. Nazemzadeh, H. Shahbazi-Alavi, Catal. Commun. 86, 14 (2016)

    Article  CAS  Google Scholar 

  80. A. Hasaninejad, N. Golzar, M. Beyrati, A. Zare, M.M. Doroodmand, J. Mol. Catal. A Chem. 372, 137 (2013)

    Article  CAS  Google Scholar 

  81. G. Ziarani, N. Lashgari, A. Badiei, M. Shakiba, Chemija 24, 142 (2013)

    CAS  Google Scholar 

  82. N. Azizi, S. Dezfooli, M. Mahmoudi Hashemi, J. Mol. Liq. 194, 62 (2014)

    Article  CAS  Google Scholar 

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Acknowledgements

We gratefully acknowledge the support and research facilities provided by the P. D. Patel Institute of Applied Sciences, CHARUSAT.

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  1. Department of Chemical Sciences, P. D. Patel Institute of Applied Sciences, Charotar University of Science and Technology (CHARUSAT), Changa, Gujarat, 388421, India

    Nipun Patel, Unnati Patel & Abhishek Dadhania

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Patel, N., Patel, U. & Dadhania, A. Highly efficient and green synthesis of spiro[indoline-3,9′-xanthene]trione and spiro[chromene-4,3′-indoline]-3-carbonitrile derivatives in water catalyzed by graphene oxide-supported dicationic ionic liquid. Res Chem Intermed 47, 2189–2206 (2021). https://doi.org/10.1007/s11164-021-04405-x

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