Document Type: Original Research Article

Authors

1 Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, P.O. BOX 14515-755, Tehran, Iran

2 Department of Chemistry, Yasouj University, Yasouj 75918-74831, Iran

10.33945/SAMI/ECC.2020.2.8

Abstract

An efficient and one-pot procedure for the preparation of 1,4-disubstituted 1,2,3-triazoles derivatives from reactions of various aryl azides and different terminal alkynes in the presence of functionalized carbon nanotubes (CNTs) by metformin and subsequent coordination with copper(I) has been developed. The catalysts showed environmentally benign character, which can be easily prepared, stored, and recovered several times without obvious significant loss of activity.

Graphical Abstract

Keywords

[1]        (a) B. Maleki, M. Baghayeri, S.A.J. Abadi, R. Tayebee, A. Khojastehnezhad, RSC Adv., 2016, 6, 96644-96661; (b) A. Javid, A. Khojastehnezhad, H. Eshghi, F. Moeinpour, F.F. Bamoharram, J. Ebrahimi, Org. Prep. Proc. Int., 2016, 48, 377-384; (c) U.U. Shaikh, Q. Tamboli, S. Pathange, Z.A. Dahan, Z. Pudukulathan, Chem. Methodol., 2018, 2, 73-82; (d) J. Sharma, R. Bansal, P. Soni, S. Singh, A. Halve, Asian J. Green Chem., 2018, 1, 135-142; (e) B. Mohammadi, L. Salmani, Asian J. Green Chem., 2018, 2, 51-58; (f) M. Soleiman-Beigi, Z. Arzehgar, Monatsh Chem., 2016, 147, 1759-1763; (g) F. Ghandehari, M. Fani, M. Rezaee, J. Med. Chem. Sci., 2018, 1, 28-30; (h) M. Keyhaniyan, A. Shiri, H. Eshghi, A. Khojastehnezhad, Appl. Organomet. Chem., 2018, 32, e4344; (i) B. Maleki, S. Barat Nam Chalaki, S. Sedigh Ashrafi, E. Rezaee Seresht, F. Moeinpour, A. Khojastehnezhad, R. Tayebee, Appl. Organomet. Chem., 2015, 29, 290-295; (j) B. Maleki, H. Eshghi, M. Barghamadi, N. Nasiri, A. Khojastehnezhad, S.S. Ashrafi, O. Pourshiani, Res. Chem. Intermed., 2016, 42, 3071-3093.

[2]        (a) M.J. Taghizadeh, S. Afghihi, H. Saidi, Asian. J. Nanosci. Mat., 2018, 1, 71-77; (b) E. Teymoori, A. Davoodnia, A. Khojastehnezhad, N. Hosseininasab, Iran. Chem. Commun., 2019, 7, 271-282; (c) M. Keyhaniyan, A. Shiri, H. Eshghi, A. Khojastehnezhad, New J. Chem., 2018, 42, 19433-19441; (d) S. Gupta, M. Lakshman, J. Med. Chem. Sci., 2019, 2, 51-54; (e) B. Maleki, E. Sheikh, E.R. Seresht, H. Eshghi, S.S. Ashrafi, A. Khojastehnezhad, H. Veisi, Org. Prep. Proced. Int., 2016, 48, 37-44; (f) A. Khojastehnezhad, M. Bakavoli, A. Javid, M.M.K. Siuki, F. Moeinpour, Catal. Lett., 2019, 149, 713-722; (g) A. Khojastehnezhad, M. Bakavoli, A. Javid, M.M.K. Siuki, M. Shahidzadeh, Res. Chem. Intermed., 2019, 1-13; (h) H. Eshghi, A. Javid, A. Khojastehnezhad, F. Moeinpour, F.F. Bamoharram, M. Bakavoli, M. Mirzaei, Chin. J. Catal., 2015, 36, 299-307; (i) H. Eshghi, A. Khojastehnezhad, F. Moeinpour, M. Bakavoli, S.M. Seyedi, M. Abbasi, RSC Adv., 2014, 4, 39782-39789; (j) H. Eshghi, A. Khojastehnezhad, F. Moeinpour, S. Rezaeian, M. Bakavoli, M. Teymouri, A. Rostami, K. Haghbeen, Tetrahedron 2015, 71, 436-444.

[3]        H. Miyagawa, M. Misra, A.K. Mohanty, J. Nanosci. & Nanotech., 2005, 5, 1593-1615.

[4]        V.N. Popov, Mat. Sci. & Eng. R. Reports 2004, 43, 61-102.

[5]        J. Che, T. Cagin, W.A. Goddard III, Nanotechnology 2000, 11, 65.

[6]        (a) C. Biswas, Y.H. Lee, Adv. Func. Mat., 2011, 21, 3806-3826; (b) P. Serp, M. Corrias, P. Kalck, Appl. Catal. A: General, 2003, 253, 337-358; (c) P. Serp, E. Castillejos, ChemCatChem 2010, 2, 41-47; (d) R.H. Baughman, A.A. Zakhidov, W.A. De Heer, Science 2002, 297, 787-792.

[7]        (a) G.G. Wildgoose, C.E. Banks, R.G. Compton, Small 2006, 2, 182-193; (b) V. Georgakilas, D. Gournis, V. Tzitzios, L. Pasquato, D.M. Guldi, M. Prato, J. Mater. Chem., 2007, 17, 2679-2694.

[8]        R. Huisgen, Angew. Chem. Int. 1963, 2, 565-598.

[9]        C.W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem., 2002, 67, 3057-3064.

[10]      V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int., 2002, 114, 2708-2711.

[11]      (a) M. Meldal, C.W. Tornøe, Chem. Rev., 2008, 108, 2952-3015; (b) M.M Heravi, H. Hamidi, V. Zadsirjan, Curr. Org. Synth. 2014, 11, 647-675.

[12]      M. Soleiman-Beigi, Z. Arzehgar, J. Sulfur Chem., 2015, 36, 395-402.

[13]      W. Zhang, X. He, B. Ren, Y. Jiang, Z. Hu, Tetrahedron Lett., 2015, 56, 2472-2475.

[14]      A.A. Ali, M. Chetia, D. Sarma, Tetrahedron Lett., 2016, 57, 1711-1714.

[15]      Y.-J. Song, C.-Y. Yoo, J.-T. Hong, S.-J. Kim, S.-U. Son, H.-Y. Jang, Bull. Korean Chem. Soc., 2008, 29, 1561-1564.

[16]      R.P. Jumde, C. Evangelisti, A. Mandoli, N. Scotti, R. Psaro, J. Catal., 2015, 324, 25-31.

[17]      L. Mohammadi, M.A. Zolfigol, A. Khazaei, M. Yarie, S. Ansari, S. Azizian, M. Khosravi, Appl. Organomet. Chem., 2018, 32.

[18]      M.K. Barman, A.K. Sinha, S. Nembenna, Green Chem., 2016, 18, 2534-2541.

[19]      H. Sharghi, R. Khalifeh, M.M. Doroodmand, Adv. Synth. Catal., 2009, 351, 207-218.

[20]      (a) E. Akhavan, S. Hemmati, M. Hekmati, H. Veisi, New J. Chem., 2018, 42, 2782-2789; (b) H. Veisi, Y. Metghalchi, M. Hekmati, S. Samadzadeh, Appl. Organomet. Chem., 2017, 31, e3676; (c) M. Baghayeri, H. Veisi, H. Veisi, B. Maleki, H. Karimi-Maleh, H. Beitollahi, RSC Adv., 2014, 4, 49595-49604.

[21]      B.E. Velasco, G. López-Téllez, N. González-Rivas, I. García-Orozco, E. Cuevas-Yañez, Can. J. Chem., 2012, 91, 292-299.

[22]      M. Chetia, P.S. Gehlot, A. Kumar, D. Sarma, Tetrahedron Lett., 2018, 59, 397-401.

[23]      M. Chetia, A.A. Ali, D. Bhuyan, L. Saikia, D. Sarma, New J. Chem., 2015, 39, 5902-5907.

[24]      N. Boechat, V.F. Ferreira, S.B. Ferreira, M.D.L.G. Ferreira, F.D.C. da Silva, M.M. Bastos, M.D.S. Costa, M.C.S. Lourenço, A.C. Pinto, A.U. Krettli, J. Med. Chem., 2011, 54, 5988-5999.

[25]      A.A. Ali, M. Chetia, P.J. Saikia, D. Sarma, RSC Adv., 2014, 4, 64388-64392.

[26]      K. Namitharan, M. Kumarraja, K. Pitchumani, Chem. Eur. J., 2009, 15, 2755-2758.

[27]      A.A. Ali, M. Chetia, B. Saikia, P.J. Saikia, D. Sarma, Tetrahedron Lett., 2015, 56, 5892-5895.

[28]      D. Wang, N. Li, M. Zhao, W. Shi, C. Ma, B. Chen, Green Chem., 2010, 12, 2120-2123.

[29]      P. Veerakumar, M. Velayudham, K.-L. Lu, S. Rajagopal, Catal. Sci. Technol., 2011, 1, 1512-1525.

[30]      F. Zareanshahraki, V. Mannari, Int. J. Cosmet. Sci. 2018, 40, 555-564.