A highly effective and mild protocol for the production of 1-thioamidoalkyl-2-naphthols using 1,3-disulfonic acid imidazolium trifluoroacetate as a dual-functional catalyst
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Mostafa Karami
Abstract
A solvent-free protocol for the production of 1-thioamidoalkyl-2-naphthols via a one-pot multi-component reaction of arylaldehydes with 2-naphthol and thioacetamide using the ionic liquid 1,3-disulfonic acid imidazolium trifluoroacetate ([Dsim][TFA]) is described. Furthermore, a plausible and attractive mechanism based on the dual functionality of the catalyst is proposed. Because of the dual functionality of [Dsim][TFA] (possessing acidic and basic sites), it is found to be generally highly effective, affording the products in high yields and short reaction times under mild conditions. We claim that this is one of the best protocols for the synthesis of 1-thioamidoalkyl-2-naphthols (in terms of yield, temperature, conditions, and/or the reaction time).
Acknowledgment
We thank Research Council of Payame Noor University for providing the necessary research facilities and financial support for carrying out this work.
References
[1] H.-X. Wei, D. Lu, V. Sun, J. Zhang, Y. Gu, P. Osenkowski, W. Ye, D. J. Selkoe, M. S. Wolfe, C. E. Augelli-Szafran, Bioorg. Med. Chem. Lett.2016, 26, 2133.10.1016/j.bmcl.2016.03.042Search in Google Scholar
[2] M. Kidwai, R. Chauhan, Asian J. Org. Chem.2013, 2, 395.10.1002/ajoc.201300039Search in Google Scholar
[3] N. Gyemant, H. Engi, Z. Schelz, I. Szatmari, D. Toth, F. Fulop, J. M. Nar, P. D. Witte, Br. J. Cancer2010, 103, 178.10.1038/sj.bjc.6605716Search in Google Scholar
[4] A. Y. Shen, C. T. Tsai, C. L. Chen, Eur. J. Med. Chem.1999, 34, 877.10.1016/S0223-5234(99)00204-4Search in Google Scholar
[5] M. Akaiwa, T. Kanbara, H. Fukumoto, T. Yamamoto, J. Organomet. Chem.2005, 690, 4192.10.1016/j.jorganchem.2005.06.026Search in Google Scholar
[6] F. Arnaud-Neu, G. Barrett, D. Corry, S. Cremin, G. Ferguson, J. F. Gallagher, S. J. Harris, M. A. McKervey, M.-J. Schwing-Weill, J. Chem. Soc., Perkin Trans.1997, 2, 575.10.1039/a605417jSearch in Google Scholar
[7] J. H. Miwa, A. K. Patel, N. Vivatrat, S. M. Popek, A. M. Meyer, Org. Lett.2001, 3, 3373.10.1021/ol0166092Search in Google Scholar PubMed
[8] J. M. Goldberg, R. F. Wissner, A. M. Klein, E. J. Petersson, Chem. Commun.2012, 48, 1550.10.1039/C1CC14708KSearch in Google Scholar
[9] F. Wang, R. Langley, G. Gulten, L. G. Dover, G. S. Besra, W. R. Jacobs Jr., J. C. Sacchettini, J. Exp. Med.2007, 204, 73.10.1084/jem.20062100Search in Google Scholar PubMed PubMed Central
[10] P. W. Tan, A. M. Mak, M. B. Sullivan, D. J. Dixon, J. Seayad, Angew. Chem. Int. Ed.2017, 56, 16550.10.1002/anie.201709273Search in Google Scholar PubMed
[11] Y. Singjunla, M. Pigeaux, R. Laporte, J. Baudoux, J. Rouden, Eur. J. Org. Chem.2017, 2017, 4319.10.1002/ejoc.201700870Search in Google Scholar
[12] M. N. Xanthopoulou, S. K. Hadjikakou, N. Hadjiliadis, E. R. Milaeva, J. A. Gracheva, V. Y. Tyurin, N. Kourkoumelis, K. C. Christoforidis, A. K. Metsios, S. Karkabounas, K. Charalabopoulos, Eur. J. Med. Chem.2008, 43, 327.10.1016/j.ejmech.2007.03.028Search in Google Scholar PubMed
[13] C. Jiang, P. J. Young, S. Brown-Xu, J. C. Gallucci, M. H. Chisholm, Inorg. Chem.2017, 56, 1433.10.1021/acs.inorgchem.6b02517Search in Google Scholar PubMed
[14] A. Khazaei, F. Abbasi, A. R. Moosavi-Zare, M. Khazaei, M. H. Beyzavi, J. Chin. Chem. Soc.2015, 62, 850.10.1002/jccs.201500125Search in Google Scholar
[15] H. Eshghi, G. H. Zohuri, S. Damavandi, Synth. Commun.2012, 42, 516.10.1080/00397911.2010.526281Search in Google Scholar
[16] A. Ghorbani-Choghamarani, S. Rashidimoghadam, Res. Chem. Intermed.2015, 41, 6271.10.1007/s11164-014-1738-ySearch in Google Scholar
[17] A. Khazaei, M. A. Zolfigol, A. R. Moosavi-Zare, F. Abi, A. Zare, H. Kaveh, V. Khakyzadeh, M. Kazem-Rostami, A. Parhami, H. Torabi-Monfared, Tetrahedron2013, 69, 212.10.1016/j.tet.2012.10.042Search in Google Scholar
[18] A. Khazaei, F. Abbasi, A. R. Moosavi-Zare, J. Sulfur Chem.2015, 36, 364.10.1080/17415993.2015.1028938Search in Google Scholar
[19] A. Zare, H. Kaveh, M. Merajoddin, A. R. Moosavi-Zare, A. Hasaninejad, M. A. Zolfigol, Phosphorus Sulfur Silicon Relat. Elem.2013, 188, 573.10.1080/10426507.2012.692131Search in Google Scholar
[20] A. Hassanabadi, M. R. Hosseini-Tabatabaei, J. Chem. Res.2012, 36, 510.10.3184/174751912X13408123396599Search in Google Scholar
[21] A. Zare, S. Akbarzadeh, E. Foroozani, H. Kaveh, A. R. Moosavi-Zare, A. Hasaninejad, M. Mokhlesi, M. H. Beyzavi, M. A. Zolfigol, J. Sulfur Chem.2012, 33, 259.10.1080/17415993.2012.690415Search in Google Scholar
[22] A. S. Amarasekara, Chem. Rev.2016, 116, 6133.10.1021/acs.chemrev.5b00763Search in Google Scholar PubMed
[23] R. L. Vekariya, J. Mol. Liq.2017, 227, 44.10.1016/j.molliq.2016.11.123Search in Google Scholar
[24] A. A. Marzouk, A. A. Abdelhamid, S. K. Mohamed, J. Simpson, Z. Naturforsch.2017, 72b, 23.10.1515/znb-2016-0121Search in Google Scholar
[25] A. K. Dutta, P. Gogoi, R. Borah, RSC Adv.2014, 4, 41287.10.1039/C4RA07323ASearch in Google Scholar
[26] M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare, H. G. Kruger, Z. Asgari, V. Khakyzadeh, M. Kazem-Rostami, J. Org. Chem.2012, 77, 3640.10.1021/jo300137wSearch in Google Scholar PubMed
[27] A. Zare, Z. Nasouri, J. Mol. Liq.2016, 216, 364.10.1016/j.molliq.2016.01.056Search in Google Scholar
[28] A. Zare, T. Yousofi, A. R. Moosavi-Zare, RSC Adv.2012, 2, 7988.10.1039/c2ra20679jSearch in Google Scholar
[29] M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Appl. Catal. A2011, 400, 70.10.1016/j.apcata.2011.04.013Search in Google Scholar
[30] A. R. Moosavi-Zare, M. A. Zolfigol, V. Khakyzadeh, C. Böttcher, M. H. Beyzavi, A. Zare, A. Hasaninejad, R. Luque, J. Mater. Chem. A2014, 2, 770.10.1039/C3TA13484ASearch in Google Scholar
[31] J. Safaei-Ghomi, S. H. Nazemzadeh, H. Shahbazi-Alavi, Z. Naturforsch.2017, 72b, 927.10.1515/znb-2017-0091Search in Google Scholar
[32] E. Lamera, S. Bouacida, M. L. Borgne, Z. Bouaziz, A. Bouraiou, Tetrahedron Lett.2017, 58, 1305.10.1016/j.tetlet.2017.02.047Search in Google Scholar
[33] M. Himaja, D. Poppy, K. Asif, Int. J. Res. Ayurveda Pharm.2011, 2, 1079.Search in Google Scholar
[34] G. B. D. Rao, S. Nagakalyanb, G. K. Prasad, RSC Adv.2017, 7, 3611.10.1039/C6RA26664ASearch in Google Scholar
[35] A. Zare, A. R. Moosavi-Zare, M. Merajoddin, M. A. Zolfigol, T. Hekmat-Zadeh, A. Hasaninejad, A. Khazaei, M. Mokhlesi, V. Khakyzadeh, F. Derakhshan-Panah, M. H. Beyzavi, E. Rostami, A. Arghoon, R. Roohandeh, J. Mol. Liq.2012, 167, 69.10.1016/j.molliq.2011.12.012Search in Google Scholar
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