Document Type: Original Research Article

Authors

1 Department of Chemistry, Payame Noor University of Bushehr, Bushehr, Iran

2 Department of Chemistry, Payame Noor University, P.O. Box 19395‐3697 Tehran, Iran

3 Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran

10.30473/icc.2019.44250.1514

Abstract

A green and highly effective solvent-free protocol has been reported for the synthesis of N,N′-alkylidene bisamides via the reaction of arylaldehydes (1 eq.) with primary amides (2 eq.) in the presence of saccharin-N-sulfonic acid (SaSA) as a solid-acid catalyst. The mentioned compounds have been obtained in high yields and short reaction times.

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[1] S.A. Ramachandran, P.S. Jadhavar, S.K. Miglani, M.P. Singh, D.P. Kalane, A.K. Agarwal, B.D. Sathe, K. Mukherjee, A. Gupta, S. Haldar, M. Raja, S. Singh, S.M. Pham, S. Chakravarty, K. Quinn, S. Belmar, I.E. Alfaro, C. Higgs, S. Bernales, F.J. Herrera, R. Rai, Bioorg. Med. Chem. Lett., 2017, 27, 2153-2160.

[2] X.-L. Wang, X.-T. Sha,G.-C. Liu, N.-L. Chen, Y. Tian, CrystEngComm, 2015, 17, 7290-7299.

[3] R.S. Mulla, M.S. Beecroft, R. Pal, J.A. Aguilar, J. Pitarch‐Jarque, E. García‐España, E. Lurie‐Luke, G.J. Sharples, J.A.G. Williams, Chem. Eur. J., 2018, 24, 7137-7148.

[4] M.-N. Chang, X.-K. Yang, P. M. Chhetri, J.-D. Chen, Polymers, 2017, 9, 691; doi:10.3390/polym9120691.

[5] M. Rodriguez, P. Dubreuil, J. P. Bali, J. Martinez, J. Med. Chem., 1987, 30, 758-763.

[6] J.W. Bode, Curr. Opin. Drug Discovery, 2006, 9, 765-775.

[7] M. Goodman, H. Shao, Pure Appl. Chem., 1996, 68, 1303-1308.

[8] T. Yamazaki, K.I. Nunami, M. Goodman, Biopolymers, 1991, 31, 1513-1528.

[9] J.P. Wan, Y.F. Chai, J.M. Wu, Y.J. Pan, Synlett, 2008, 19, 3068-3072.

[10] A.H. Fernandez, R.M. Alvarez, T.M. Abajo, Synthesis, 1996, 1299-1301.

[11] H.R. Saadati-Moshtaghin, F.M. Zonoz, M.M. Amini, J. Solid State Chem., 2018, 260, 16-22.

[12] T.L. Lambat, S.S. Deo, F.S. Inam, T.B. Deshmukh, A.R. Bhat, Karbala Int. J. Modern Sci., 2016, 2, 63-68.

[13] M. Tajbakhsh, R. Hosseinzadeh, H. Alinezhad, P. Rezaee, Synth. Commun., 2013, 43, 2370-2379.

[14] B. Maleki, M. Baghayeri, RSC Adv., 2015, 5, 79746-79758.

[15] M. Kour, S. Paul, New J. Chem., 2015, 39, 6338-6350.

[16] G. Ramachandran, R. Saraswathi, M. Kumarraja, P. Govindaraj, T. Subramanian, Synth. Commun., 2018, 48, 216-222.

[17] H.A. Soliman, A.Y. Mubarak, S.S. Elmorsy, Chin. Chem. Lett., 2016, 27, 353-356.  

[18] B. Maleki, F. Mohammadi Zonoz, H.A. Akhlaghi, Org. Prep. Proced. Int., 2015, 47, 361-367.

[19] Z. Karimi-Jaberi, B. Pooladian, Monatsh. Chem., 2013, 144, 659-663.

[20] E. Noroozizadeh, A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, R. Karamian, M. Asadbegy, S. Yari, S.H. Moazzami Farida, J. Iran. Chem. Soc., 2018, 15, 471-481.[21] F. Shirini, M.A. Zolfigol, M. Abedini, Monatsh. Chem.,2009, 140, 1495-1498.

[22] F. Shirini, M.A. Zolfigol, M. Abedini, J. Iran. Chem. Soc.,2010, 7, 603-607.

[23] M.A. Zolfigol, M. Navazeni, M. Yarie, R. Ayazi-Nasrabadi, Res. Chem. Intermed., 2018, 44, 191-200.

[24] A. Nakhaei, A. Davoodnia, S. Yadegarian, Iran. Chem. Commun., 2018, 6, 334-345. 

[25] A. Khazaei, N. Sarmasti, J. Yousefi Seyf, Appl. Organomet. Chem., 2018, 32, e4308.

[26] A. Zare, H. Asvar, F. Zarei, M. Khalili, Z. Kordrostami, A.R. Moosavi-Zare, V. Khakyzadeh, J. Appl. Chem. Res., 2016, 10, 59-67.

[27] A. Zare, J. Sanjideh, Iran. Chem. Commun., 2018, 6, 416-422.

[28] A. Zare, M. Maghsoudi, B. Gholami, A.R. Moosavi-Zare, J. Appl. Chem. Res., 2016, 10, 31-39.

[29] A. Zare, A. Kohzadiana, Z. Abshirini, S.S. Sajadikhah, J. Phipps, M. Benamara, M.H. Beyzavi, New J. Chem., 2019, 43, 2247-2257.

[30] S. Sajjadifar, G. Mansouri, S. Miraninezhad, Asian J. Nano. Mat., 2018, 1, 11-18.

[31] N. Noroozi Pesyan, A. Gharib, A. Monfared, Iran. Chem. Commun., 2018, 6, 346-358.

[32] N. Irannejad-Gheshlaghchaei, A. Zare, S.S. Sajadikhah, A. Banaei, Res. Chem. Intermed., 2018, 44, 6253-6266.