Document Type: Original Research Article

Authors

1 Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

2 Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran

10.33945/SAMI/ECC.2020.3.4

Abstract

The catalytic activity of newly prepared functionalized graphene oxide nanosheets, denoted as GO-SB-H2PMo, has been investigated in the synthesis of amidoalkyl naphthols through the one-pot, three-component reaction of β‐naphthol with various aryl aldehydes and acetamide. The reactions occur under solvent-free conditions and the process is operative with various aryl aldehydes, giving the corresponding products in high yields over short reaction times. Moreover, the catalyst could be easily recovered from the reaction mixture and reused such that considerable catalytic activity can still be achieved after the fifth run.

Graphical Abstract

Keywords

[1]        A. Maleki, V. Eskandarpour, J. Iran. Chem. Soc., 2019, 16, 1459-1472.

[2]        A. Maleki, M. Aghaei, N. Ghamari, Appl. Organometal. Chem., 2016, 30, 939-942.

[3]        H. Salavati, A. Teimouri, S. KazemiChem. Methodol., 2017, 112-27.

[4]        S.A. Moghadam Ziabari, M. Babamoradi, Z. Hajizadeh, A. Maleki,  Iran. Chem. Commun., 2019, 7, 512-520.

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

[6]        A. Nakhaei, A. Davoodnia, H. Nakhaei, J. Chem. Rev., 2019, 1, 139-153.

[7]        S. Sajjadifar, Z. Arzehgar, S. Khoshpoori, J. Inorg. Organomet. Polym. Mater., 2018, 28, 837-846.

[8]        S. Sajjadifar, K. Pal, H. Jabbari, O. Pouralimardan, F. Divsar, S. Mohammadi-Aghdam, I. Amini, H. Hamidi,  Chem. Methodol., 2019, 3, 226-236.

[9]        Z. Arzehgar, V. Azizkhani, S. Sajjadifar, M.H. Fekri, Chem. Methodol., 2019, 3, 251-260.

[10]      R. Kaur, K. Kumar, J. Med. Chem. Sci., 2019, 2, 110-117.

[11]      M. Soleiman-Beigi, Z. Arzehgar, Synlett, 2018, 29, 986-992.

[12]      M.M. Heravi, H.A. Oskooie, N. Karimi, H. Hamidi, Chin. Chem. Lett., 2011, 22, 1059-1062.

[13]      A. Maleki, R. Ghalavand, R. Firouzi-Haji, Iran. J. Catal., 2018, 8, 221-229.

[14]      M.M. Heravi, H. Hamidi, N. Karimi, A. Amouchi, Adv. J. Chem. A, 2018, 1, 1-6.

[15]      A. Nakhaei, Curr. Catal., 2018, 7, 72-78.

[16]      A. Nakhaei, Heterocycl. Lett., 2018, 8, 579-586.

[17]      A. Nakhaei, H. Nakhaei, Heterocycl. Lett., 2018, 8, 27-33.

[18]      W.S. Hummers, R.E. Offeman, J. Am. Chem. Soc., 1958, 80, 1339-1339.

[19]      D.R. Dreyer, S. Park, C.W. Bielawski, R.S. RuoffChem. Soc. Rev., 2010, 39, 228-240.

[20]      S. Kumari, A. Shekhar, D.D. Pathak, RSC Adv., 2014, 4, 61187-61192.

[21]      J. Zhao, Y. Xie, J. Fang, Y. Ling, Y. Gao, X. Liu, Q. Zhang, Q. Xu, H. Xiong, J. Mater. Sci., 2016, 51, 10574-10584.

[22]      J. Li, H. Xu, Talanta2017, 167, 623-629.

[23]      E. Kowsari, M.R. Chirani, Carbon, 2017, 118, 384-392.

[24]      Y. Wu, Z. Zhao, M. Chen, Z. Jing, F. Qiu, Monatsh. Chem., 2018, 149, 1367-1377.

[25]      S. Rostamizadeh, M. Rezgi, N. Shadjou, M. Hasanzadeh, J. Chin. Chem. Soc., 2013, 60, 1317-1322.

[26]      P.K. Khatri, S. Choudhary, R. Singh, S.L. Jain, O.P. Khatri, Dalton Trans., 2014, 43,

8054-8061.

[27]      S. Rayati, E. Khodaei, S. Shokoohi, M. Jafarian, B. Elmi, A. Wojtczak, Inorg. Chim. Acta, 2017, 466, 520-528.

[28]      M. Cano, U. Khan, T. Sainsbury, A. O’Neill, Z. Wang, I.T. McGovern, W.K. Maser, A.M. Benito, J.N. Coleman, Carbon, 2013, 52, 363-371.

[29]      S. Stankovich, R.D. Piner, S.T. Nguyen, R.S. Ruoff, Carbon, 2006, 44, 3342-3347.

[30]      B. Konkena, S. Vasudevan, Langmuir, 2012, 28, 12432-12437.

[31]      S. Verma, M. Aila, S. Kaul, S.L. Jain, RSC Adv., 2014, 4, 30598-30604.

[32]      S. Kumari, A. Shekhar, D.D. Pathak, RSC Adv., 2016, 6, 15340-15344.

[33]      R.R. Nagawade, D.B. Shinde, Mendeleev Commun., 2007, 17, 299-300.

[34]      L. Nagarapu, M. Baseeruddin, S. Apuri, S. Kantevari, Catal. Commun., 2007, 8, 1729-1734.

[35]      W.-Q. Jiang, L.-T. An, J.-P. Zou, Chin. J. Chem., 2008, 26, 1697-1701.

[36]      H.R. Shaterian, A. Amirzadeh, F. Khorami, M. Ghashang, Synth. Commun., 2008, 38, 2983-2994.

[37]      A. Kumar, M.S. Rao, I. Ahmad, B. Khungar, Can. J. Chem., 2009, 87, 714-719.

[38]      M. Lei, L. Ma, L. Hu, Tetrahedron Lett., 2009, 50, 6393-6397.

[39]      M. Wang, Y. Liang, Monatsh. Chem., 2011, 142, 153-157.

[40]      A. Zali, A. Shokrolahi, Chin. Chem. Lett., 2012, 23, 269-272.

[41]      A. Davoodnia, R. Mahjoobin, N. Tavakoli-Hoseini, Chin. J. Catal., 2014, 35, 490-495.

[42]      A. Bamoniri, B.F. Mirjalili, S. Nazemian, J. Iran. Chem. Soc., 2014, 11, 653-658.

[43]      S. Sheik Mansoor, K. Aswin, K. Logaiya, S.P.N. Sudhan, J. Saudi Chem. Soc., 2016, 20, 138-150.

[44]      A.R. Kiasat, L. Hemat-Alian, S.J. Saghanezhad, Res. Chem. Intermed., 2016, 42, 915-922.

[45]      S. Khanapure, M. Jagadale, R. Salunkhe, G. Rashinkar, Res. Chem. Intermed., 2016, 42, 2075-2085.

[46]      M. Kooti, M. Karimi, E. Nasiri, J. Nanopart. Res., 2018, 20, Art. No. 16.

[47]      S. Puri, B. Kaur, A. Parmar, H. Kumar, Org. Prep. Proced. Int., 2012, 44, 91-95.

[48]      M. Rohaniyan, A. Davoodnia, S.A. Beyramabadi, A. Khojastehnezhad, Appl. Organometal. Chem., 2019, 33, Art. No. e4881.

[49]      A. Emrani, A. Davoodnia, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc., 2011, 32, 2385-2390.

[50]      A. Davoodnia, A. Khojastehnezhad, M. Bakavoli, N. Tavakoli‐Hoseini, Chin. J. Chem., 2011, 29, 978-982.

[51]      A. Davoodnia, A. Khojastehnezhad, A. J. Chil. Chem. Soc., 2012, 57, 1385-1387.

[52]      A. Davoodnia, M. Khashi, N. Tavakoli-Hoseini, Chin. J. Catal., 2013, 34, 1173-1178.

[53]      M. Khashi, A. Davoodnia, V.S. Prasada Rao Lingam, Res. Chem. Intermed., 2015, 41, 5731-5742.

[54]      A. Davoodnia, A. Nakhaei, N. Tavakoli-Hoseini, Z. Naturforsch., 2016, 71b, 219-225.

[55]      S. Ameli, A. Davoodnia, M. Pordel, Org. Prep. Proced. Int., 2016, 48, 328-336.

[56]      M. Fattahi, A. Davoodnia, M. Pordel, Russ. J. Gen. Chem., 2017, 87, 863-867.

[57]      N. Hosseininasab, A. Davoodnia, F. Rostami-Charati, A. Khojastehnezhad, Russ. J. Gen. Chem., 2017, 87, 2436-2443.

[58]      F. Tajfirooz, A. Davoodnia, M. Pordel, M. Ebrahimi, A. Khojastehnezhad, Appl. Organometal. Chem., 2018, 32, Art. No. e3930.

[59]      E. Teymooria, A. Davoodnia, A. Khojastehnezhad, N. Hosseininasab, Iran. Chem. Commun., 2019, 7, 271-282.