Document Type: Original Article

Authors

1 Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran‎

2 Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran

Abstract

N,N,N',N'-tetramethyl-N,N'-bis(sulfo)ethane-1,2-diaminium mesylate ‎‎([TMBSED][Oms]2) is used as a highly efficient and dual-functional catalyst for the one-pot multi-component condensation of 2-naphthol with arylaldehydes and thioacetamide under green, mild (70 °C), and solvent-free conditions. In this reaction, 1-thioamidoalkyl-2-naphthols are produced in high to excellent yields and in relatively short reaction times. In this reaction, products are identified by analysis of its 1H NMR, 13C NMR, and FT-IR data. Moreover, a plausible mechanism based on dual-functionality of the catalyst was proposed.

Graphical Abstract

Keywords

[1] Devi I., Bhuyan P.J. Tetrahedron Lett., 2004, 45:8625

‎[2] ‎Mashraqui S.H., Patil M.B., Mistry H.D., Ghadigaonkar S., Meetsma A.‎ Chem. Lett., 2004, 33:1058

[3] Karami M., Gholami B., Hekmat-Zadeh T., Zare A. Chem. Methodol., 2019, 3:509

[4] Taghavi Fardood S., Ramazani A., Ayubi M., Moradnia F., Abdpour S., Forootan R. Chem. Methodol., 2019, 3:583

[5] Abshirini Z., Zare A. Z. Naturforsc., 2018, 73b:191

[6] Sujatha K., Vedula R.R. J. Heterocyclic. Chem., 2019, 56:832

[7] Kumari S., Kumar D., Gajaganti S., Srivastava V., Singh S. Synth. Commun., 2019, 49:431

[8] ‏Kumari P., Bharti R., Parvin T. Mol. Divers., 2019, 23:205

[9] Shen A.Y., Tsai C.T., Chen C.L. Eur. J. Med. Chem., 1999, 34:877

[10] Gyémánt N., Engi H., Schelz Z., Szatmári I., Tóth D., Fülöp F., Molnár J., de Witte P.A.M., Br. J. Cancer, 2010, 103:178

[11] Kidwai M., Chauhan R. Asian J. Org. Chem., 2013, 2:395

[12] Wei H.X., Lu D., Sun V., Zhang J., Gu Y., Osenkowski P., Ye W., Selkoe D.J., Wolfe M.S., Augelli-Szafran C.E. Bioorg. Med. Chem. Lett., 2016, 26:2133

[13] Hassanabadi A., Hosseini-Tabatabaei M.R. J. Chem. Res., 2012, 36:510

[14] Eshghi H., Zohuri G.H., Damavandi S. Synth. Commun., 2012, 42:516

[15] Ghorbani-Choghamarani A., Rashidimoghadam S. Res. Chem. Intermed., 2015, 41:6271

[16] Khazaei A., Abbasi F., Moosavi‐Zare A.R., Khazaei M., Beyzavi M.H. J.Chin. Chem Soc., 2015, 62:850

[17] Khazaei A., Zolfigol M.A., Moosavi-Zare A.R., Abi F., Zare A., Kaveh H., Khakyzadeh V., Kazem-Rostami M., Parhami A., Torabi-Monfared H. Tetrahedron, 2013, 69:212

[18] Saadat A., Zare A., Jamadi F., Abdolalipour-Saretoli M. Bull. Chem. React. Eng. Catal., 2018, 13:204

[19] Khazaei A., Abbasi F., Moosavi-Zare A.R. J. Sulfur Chem., 2015, 36:364

[20] Zare A., Kaveh H., Merajoddin M., Moosavi-Zare A.R., Hasaninejad A., Zolfigol M.A. Phosphorus Sulfur Silicon Relat. Elem., 2013, 188:573

[21] Ghorbani-Choghamarani A., Rashidimoghadam S. Chin. J. Catal., 2014, 35:1024

[22] Shaterian H.R., Azizi K., Fahimi N. Res. Chem. Intermed., 2014, 40:2613

[23] Lang X.D., Li Z.M., He L.N. Catal. Today., 2019, 324:167

[24] Ullah Z., Bustam M.A., Man Z., Khan A.S., Sarwono A., Muhammad N., Farooq N., Shah S.N., Ahmad, P., Haider S. Int. J. Environ. Sci.,‏ 2019, 16:1269

[25] Keshapolla D., Srinivasarao K., Gardas R.L. J. Chem. Therm., 2019, 133:170

[26] Kanj A.B., Verma R., Liu M., Helfferich J., Wenzel W., Heinke L. Nano Lett., 2019, 19:2114

[27] Kargar-Dolatabadi A., Zare A. Chem. Methodol., 2019, 3:655

[28] Zare A., Nasouri Z. J. Mol. Liq., 2016, 216:364

[29] Reddy A.R., Farooq S., Dar B.A. Chem. Methodol., 2019, 3:663

[30] Zare A., Sharif E., Arghoon A., Ghasemi M., Dehghani B., Ahmad-Zadeh S., Zarei F. Iran. J. Catal., 2017, 7:233

[31] Irannejad-Gheshlaghchaei N., Zare A., Sajadikhah S.S., Banaei A. Res. Chem. Intermed., 2018, 44:6253