Synthesis of 1,4-Disubstituted-1,2,3-Triazoles Catalyzed by Part-per-Million CuIin Magnetized DistilledWater

Subject Areas : Polymer

Mohammad Bakherad ¹ , Ali Keivanloo ² , Atefeh Abdia ³ , Soghra Kamrani Tamardasha ⁴

1 - Faculty of Chemistry, Shahrood University of Technology, Shahrood , Iran.
2 - Faculty of Chemistry, Shahrood University of Technology, Shahrood, Iran.
3 - Faculty of Chemistry, Shahrood University of Technology, Shahrood, Iran.
4 - Faculty of Chemistry, Shahrood University of Technology, Shahrood, Iran.

Received: 2022-04-23 Accepted : 2022-04-23 Published : 2022-07-01

Keywords:

Abstract :

The use of an extremely low quantity of copper is always a significant factor in Cu-catalyzed azide-alkyne cycloaddition reaction (CuAAC).Aninsignificant quantity of CuIshowed excellent catalytic activity for the clickreaction of terminal alkynes, benzyl chloride derivatives,and sodium azide in magnetized distilled water (MDW) as a green solvent.

References:

[1]. G.C. Tron, T. Pirali, R.A. Billington, P.L. Canonico, G. Sorba, A.A. Genazzani, Med. Res. Rev.,
28, 278 (2008).
[2]. H.Y. Guo, F.F. Yang, Z.Y. Jiao, J.R. Lin, Chin. Chem. Lett., 24, 450 (2013).
[3]. Y. Zhang, V.K.R. Tangadanchu, R. Rammohan, Y. Bheemanaboina, Y. Cheng. H.Z. Cheng,
Eur. J. Med. Chem., 155, 579 (2018).
[4]. K. Pluta, B. Morak-Młodawska, M. Jeleń, Eur. J. Med. Chem., 46, 3179 (2011).
[5]. F. Suzuki, K. Hashimoto, M. Ishihara, G. Westman, K. Samuelsson, M. Kawase, N. Motohashi,
H. Sakagami, Anticancer Res., 27, 4233 (2007).
[6]. S.R. Patpi, L. Pulipati, P. Yogeeswari, D. Sriram, N. Jain, B. Sridhar, S. Kantevari, J. Med.
Chem. 55, 3911 (2012).
[7]. V.R. Vsevolod, G.G. Luke, V.F. Valery, K.B. Sharpless, Chem. Int. Ed., 114, 2596 (2002).
[8]. G.A. Molander, J. Ham, Org. Lett., 13, 2767 (2006).
[9]. F. Ilgen, B. Konig, Green Chem., 11, 848 (2009).
[10]. F. Alonso, Y. Moglie, G. Radivoy, M. Yus, Synlett, 23, 2179 (2012).
[11]. S. Lal, S. Díez-Gonzalez, J. Org. Chem., 76, 2367 (2011).
[12]. N. Mukherjee, S. Ahammed, S. Bhadra, B.C. Ranu, Green Chem., 15, 389 (2013).
[13]. A.K. Feldman, B. Colasson, V.V. Fokin, Org. Lett., 22, 3897 (2004).
[14]. H. Sharghi, R. Khalifeh, M.M. Doroodmand, Adv. Synth. Catal., 351, 207 (2009).
[15]. P. Veerakumar, M. Velayudham, K.L. Lub, S. Rajagopal, Catal. Sci. Technol. 1, 1512 (2011).
[16]. C. Ornelas, J. Ruiz Aranzaes, E. Cloutet, S. Alves, D. Astruc, Angew,Chem. Int. Ed., 119, 890
(2007).
[17]. D. Astruc, L. Liang, A. Rapakousiou, J. Ruiz, Acc. Chem. Res., 45, 630 (2012).
[18]. V.K. Golovleva, G.E. Dunaevskii, T.L. Levdikova, Y.S. Sarkisov, Y.I. Tsyganok, Russ. Phys.
J., 43, 1009 (2000).
[19]. O. Mosin, I. Ignatov, Nanotechnol. Res. Pract., 4, 187 (2014).
[20]. O. Mosin, I. Ignatov, Nanotechnol. Res. Pract., 6, 81 (2015).
[21]. E. Esmaeilnezhad, H.L. Choi, M. Schaffie, M. Gholizadeh, M. Ranjbar, J. Clean. Prod., 161,
908 (2017).
[22]. Y. Absalan, M. Gholizadeh, H.J. Choi, J. Mol. Liq.,335, 116167 (2021).
[23]. M. Bakherad, A. Keivanloo, M. Gholizadeh, R. Doosti, M. Javanmardi, Res. Chem. Intermed.,
43,1013 (2017). 

[24]. M. Bakherad, R. Doosti, A. Keivanloo, M. Gholizadeh, A.H. Amin, Lett. Org. Chem., 14, 510
(2017).
[25]. M. Bakherad, G.A. Bagherian, A. Rezaeifard, F. Mosayebi, B. Shokoohi, A. Keivanloo, J.
Iran. Chem. Soc., 18, 839 (2021).
[26]. M.Bakherad, Z. Moosavi-tekyeh, A. Keivanloo, M. Gholizadeh, Z. Toozandehjani, Res. Chem.
Intermed., 44, 373 (2018).
[27]. C. Deraedt, N. Pinaud, D. Astruc, J. Am. Chem. Soc., 136, 12092 (2014).
[28]. N. Candelon, D. Laste´coue`res, A. Khadri Diallo, J. Ruiz Aranzaes, D. Astruc, J.M. Vincent,
Chem. Commun., 741, 741 (2008).
[29]. B.S.P. Anil Kumar, K.H.V. Reddy, B. Madhav, K. Ramesh, Y.V.D. Nageswar, Tetrahedron
Lett., 53, 4595 (2012).
[30]. S.B. Otvos, G. Hatoss, A. Georgiades, S. Kovacs, I.M. Mandity, Z. Novak, F. Fulop, RSC
Adv., 4, 46666 (2014).
[31]. R. Sasikala, S.K. Rani, D. Easwaramoorthy, K. Karthikeyan, RSC Adv.5, 56507 (2015).
[32]. K. Lal, P. Yadav, A. Kumar, Med. Chem. Res.,25, 644 (2016).
[33]. M. Bakherad, R. Doosti, Z. Qasemifar, J. Appl. Chem. Res.,14, 8 (2020).