Abstract
A highly efficient and green protocol for the synthesis of 3,3′-(arylmethylene)-bis(2-hydroxynaphthoquinone) {3,3′-(arylmethylene)-bis(2-hydroxynaphthalene-1,4-dione)} derivatives has been developed. The reaction of 2-hydroxynaphthoquinone (2-hydroxynaphthalene-1,4-dione) (2 eq.) and arylaldehydes (1 eq.) in the presence of the dicationic molten salt N,N,N′,N′-tetramethylethylenediaminium bis-hydrogensulfate ([TMEDAH2][HSO4]2) under solvent-free conditions afforded the mentioned compounds in high yields and relatively short reaction times.
Funding source: Payame Noor University
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: We thank Research Council of Payame Noor University for the support of this work.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. de Carvalho da Silva, F., Ferreira, V. F. Curr. Org. Synth. 2016, 13, 334–371.10.2174/1570179412666150817220343Search in Google Scholar
2. Guiraud, P., Steiman, R., Campos-Takaki, G. M., Seigle-Murandi, F., Simeon, B. M. Planta Med. 1994, 60, 373–374.10.1055/s-2006-959504Search in Google Scholar
3. Esteves-Souza, A., Lucio, K. A., Da Cunha, A. S., Da Cunha Pinto, A., Da Silva Lima, E. L., Camara, C. A., Vargas, M. D., Gattass, C. R. Oncol. Rep. 2008, 20, 225–231.Search in Google Scholar
4. Ryu, C.-K., Kim, D.-H. Arch. Pharm. Res. 1992, 15, 263–268.10.1007/BF02974067Search in Google Scholar
5. de Almeida, E. R., Silva Filho, A. A., Santos, E. R., Lopes, C. A. J. Ethnopharmacol. 1990, 29, 239–241.10.1016/0378-8741(90)90061-WSearch in Google Scholar
6. Tandon, V. K., Yadav, D. B., Singh, R. V., Vaish, M., Chaturvedi, A. K., Shukla, P. K. Bioorg. Med. Chem. Lett. 2005, 15, 3463–3466.10.1016/j.bmcl.2005.04.075Search in Google Scholar
7. Bonifazi, E. L., Ríos-Luci, C., León, L. G., Burton, G., Padrón, J. M., Misico, R. I. Bioorg. Med. Chem. 2010, 18, 2621–2630.10.1016/j.bmc.2010.02.032Search in Google Scholar
8. Brun, M.-P., Braud, E., Angotti, D., Mondésert, O., Quaranta, M., Montes, M., Miteva, M., Gresh, N., Ducommun, B., Garbay, C. Bioorg. Med. Chem. 2005, 13, 4871–4879.10.1016/j.bmc.2005.05.005Search in Google Scholar
9. Tandon, V. K., Yadav, D. B., Singh, R. V., Chaturvedi, A. K., Shukla, P. K. Bioorg. Med. Chem. Lett. 2005, 15, 5324–5328.10.1016/j.bmcl.2005.08.032Search in Google Scholar
10. Huang, L.-J., Chang, F.-C., Lee, K.-H., Wang, J.-P., Teng, C.-M., Kuo, S.-C. Bioorg. Med. Chem. 1998, 6, 2261–2269.10.1016/S0968-0896(98)80006-0Search in Google Scholar
11. Novais, J. S., Rosandiski, A. C., de Carvalho, C. M., de Saules Silva, L. S., dos S Velasco de Souza, L. C., Santana, M. V., Martins, N. R. C., Castro, H. C., Ferreira, V. F., Gonzaga, D. T. G., de Resende, G. O., de Carvalho da Silva, F. Curr. Top. Med. Chem. 2020, 20, 121–131.10.2174/1568026619666191210160342Search in Google Scholar PubMed
12. de Oliveira, A. S., Lianes, L. C., Nunes, R. J., Yunes, R. A., Brighente, I. M. C. Green Sustain. Chem. 2014, 4, 177–184.10.4236/gsc.2014.44023Search in Google Scholar
13. Khurana, J. M., Lumb, A., Chaudhary, A., Nand, B. J. Heterocycl. Chem. 2014, 51, 1747–1751.10.1002/jhet.1871Search in Google Scholar
14. Tisseh, Z. N., Bazgir, A. Dyes Pigm. 2009, 83, 258–261.10.1016/j.dyepig.2008.09.003Search in Google Scholar
15. Wang, H., Wang, Z., Wang, C., Yang, F., Zhang, H., Yuea, H., Wang, L. RSC Adv. 2014, 4, 35686–35689.10.1039/C4RA06516FSearch in Google Scholar
16. Asghari-Haji, F., Rad-Moghadam, K., Mahmoodi, N. O. RSC Adv. 2016, 6, 27388–27394.10.1039/C5RA26580KSearch in Google Scholar
17. Li, Y., Du, B., Xu, X., Shi, D., Ji, S. Chin. J. Chem. 2009, 27, 1563–1568.10.1002/cjoc.200990264Search in Google Scholar
18. Brahmachari, G. ACS Sustain. Chem. Eng. 2015, 3, 2058–2066.10.1021/acssuschemeng.5b00325Search in Google Scholar
19. Zolfigol, M. A., Bahrami-Nejad, N., Baghery, S. J. Mol. Liq. 2016, 218, 558–564.10.1016/j.molliq.2016.03.006Search in Google Scholar
20. Zare, A., Ghobadpoor, A., Safdari, T. Res. Chem. Intermed. 2020, 46, 1319–1327.10.1007/s11164-019-04036-3Search in Google Scholar
21. Liu, L., Yao, S., Liang, B., Li, W. Res. Chem. Intermed. 2019, 45, 893–905.10.1007/s11164-018-3650-3Search in Google Scholar
22. Dashteh, M., Baghery, S., Zolfigol, M. A., Bayat, Y., Asgari, A. ChemistrySelect 2019, 4, 337–346.10.1002/slct.201803402Search in Google Scholar
23. Yarie, M., Zolfigol, M. A., Babaee, S., Baghery, S., Alonso, D. A., Khoshnood, A. Res. Chem. Intermed. 2018, 44, 2839–2852.10.1007/s11164-018-3264-9Search in Google Scholar
24. Babaee, S., Zolfigol, M. A., Zarei, M., Zamanian, J. ChemistrySelect 2018, 3, 8947–8954.10.1002/slct.201801476Search in Google Scholar
25. Zolfigol, M. A., Baghery, S., Moosavi-Zare, A. R., Vahdat, S. M., Alinezhad, H., Norouzi, M. RSC Adv. 2015, 5, 45027–45037.10.1039/C5RA02718GSearch in Google Scholar
26. Tian, L., Li, J., Liang, F., Chang, S., Zhang, H., Zhang, M., Zhang, S. J. Colloid Interface Sci. 2019, 536, 664–672.10.1016/j.jcis.2018.10.098Search in Google Scholar PubMed
27. Tian, L., Li, J., Liang, F., Wang, J., Li, S., Zhang, H., Zhang, S. Appl. Catal. B 2018, 225, 307–313.10.1016/j.apcatb.2017.11.082Search in Google Scholar
28. Zare, A., Hasaninejad, A., Beyzavi, M. H., Parhami, A., Moosavi Zare, A. R., Khalafi-Nezhad, A., Sharghi, H. Can. J. Chem. 2008, 86, 317–324.10.1139/v08-022Search in Google Scholar
29. Kamali, A. Green Production of Carbon Nanomaterials in Molten Salts and Applications; Springer: Singapore, 2020.10.1007/978-981-15-2373-1Search in Google Scholar
30. Yi, Z., Lin, N., Zhang, W., Wang, W., Zhu, Y., Qian, Y. Nanoscale 2018, 10, 13236–13241.10.1039/C8NR03829ESearch in Google Scholar PubMed
31. Imanzadeh, G. H., Khalafi-Nezhad, A., Zare, A., Hasaninejad, A., Moosavi Zare, A. R., Parhami, A. J. Iran. Chem. Soc. 2007, 4, 229–237.10.1007/BF03245971Search in Google Scholar
32. Liu, S., Han, W., Cui, B., Liu, X., Zhao, F., Stuart, J., Licht, S. J. Power Sources 2017, 342, 435–441.10.1016/j.jpowsour.2016.12.080Search in Google Scholar
33. Rodríguez-Sánchez, M. R., Sánchez-González, A., Marugán-Cruz, C., Santana, D. Energy Procedia 2014, 49, 504–513.10.1016/j.egypro.2014.03.054Search in Google Scholar
34. Wang, M., Tan, Q., Liu, L., Li, J. ACS Sustain. Chem. Eng. 2019, 7, 8287–8294.10.1021/acssuschemeng.8b06694Search in Google Scholar
35. Wang, W., Wu, Z., Li, B., Sundén, B. J. Therm. Anal. Calorim. 2019, 136, 1037–1051.10.1007/s10973-018-7765-ySearch in Google Scholar
36. Zoua, L.-L., Chena, X., Wua, Y.-T., Wang, X., Ma, C.-F. Sol. Energy Mater. Sol. Cells 2019, 190, 12–19.10.1016/j.solmat.2018.10.013Search in Google Scholar
37. Himaja, M., Poppy, D., Asif, K. Int. J. Res. Ayurveda Pharm. 2011, 2, 1079–1086.Search in Google Scholar
38. Zare, A., Lotfifar, N., Dianat, M. J. Mol. Struct. 2020, 1211, 128030.10.1016/j.molstruc.2020.128030Search in Google Scholar
39. Kordnezhadian, R., Shekouhy, M., Karimian, S., Khalafi-Nezhad, A. J. Catal. 2019, 380, 91–107.10.1016/j.jcat.2019.10.020Search in Google Scholar
40. Kordrostami, Z., Zare, A., Karami, M. Z. Naturforsch. 2019, 74b, 641–647.10.1515/znb-2019-0064Search in Google Scholar
41. Afsharpour, R., Zanganeh, S., Kamantorki, S., Fakhraei, F., Rostami, E. Asian J. Nanosci. Mater. 2020, 3, 148–156.Search in Google Scholar
42. Zare, A., Dianat, M., Eskandari, M. M. New J. Chem. 2020, 44, 4736–4743.10.1039/C9NJ06393ESearch in Google Scholar
43. Khanivar, R., Zare, A. Z. Naturforsch. 2018, 73b, 635–640.10.1515/znb-2018-0075Search in Google Scholar
Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/znb-2020-0174).
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