Nanoporous metal-organic framework Cu2(BDC)2(DABCO) as an efficient heterogeneous catalyst for one-pot facile synthesis of 1,2,3-triazole derivatives in ethanol: Evaluating antimicrobial activity of the novel derivatives

Document Type : Article

Authors

Research Laboratory of Green Organic Synthesis & Polymers, Department of Chemistry, Iran University of Science and Technology, Tehran, P.O. Box 16846-13114, I.R. Iran.

Abstract

Solvent-free ball-milling synthesized porous metal-organic framework Cu2(BDC)2(DABCO) (BDC: benzene-1,4-dicarboxylic acid, DABCO: 1,4-diazabicyclo[2.2.2]octane) proved to be a practical catalyst for facile and convenient synthesis of 1,2,3–triazole derivatives via multicomponent reaction of terminal alkynes, benzyl or alkyl halides, and sodium azide in ethanol. Avoidance of usage and handling of hazardous organic azides, using ethanol as an easy available solvent and catalyst simple preparation and its recycling makes this procedure truly a scale-up-able method. The high loading of copper ions in the catalyst causes efficient catalytic activity and hence its low weight usage in reaction. The catalyst was recycled and reused several times without significant loss of its activity. Furthermore, novel derivatives were examined to investigate their potential antimicrobial activity via microdilution method.

Keywords

Main Subjects


1. Petrova, K.T., Potewar, T.M., Correia-da-Silva, P., Barros, M.T., Calhelha, R.C., _Ciric, A., Sokovi_c, M., and Ferreira, I.C.F.R. Antimicrobial and cytotoxic activities of 1,2,3-triazole-sucrose derivatives", Carbohydr. Res., 417, pp. 66-71 (2015). 2. Dai, Z.C., Chen, Y.F., Zhang, M., Li, S.K., Yang, T.T., Shen, L., Wang, J.X., Qian, S.S., Zhu, H.L., and Ye, Y.H. Synthesis and antifungal activity of 1,2,3- triazole phenylhydrazone derivatives", Org. Biomol. Chem., 13(2), pp. 477-486 (2015). 3. Hou, W., Luo, Z., Zhang, G., Cao, D., Li, D., Ruan, H., Ruan, B.H., Su, L., and Xu, H. Click chemistrybased synthesis and anticancer activity evaluation of novel C-14 1,2,3-triazole dehydroabietic acid hybrids", Eur. J. Med. Chem., 138, pp. 1042-1052 (2017). 4. Lazrek, H., Taourirte, M., Oulih, T., Barascut, J., Imbach, J., Pannecouque, C., Witrouw, M., and De Clercq, E. Synthesis and anti-HIV activity of new modi_ed 1, 2, 3-triazole acyclonucleosides", Nucleosides, Nucleotides Nucleic Acids, 20(12), pp. 1949- 1960 (2001). 5. Gavlik, K.D., Sukhorukova, E.S., Shafran, Y.M., Slepukhin, P.A., Benassi, E., and Belskaya, N.P. 2-aryl-5-amino-1,2,3-triazoles: new e_ective blueemitting uorophores", Dyes Pigm., 136, pp. 229-242 (2017). 6. Gonz_alez-Olvera, R., Rom_an-Rodr__guez, V., Negr_on- Silva, G.E., Espinoza-V_azquez, A., Rodr__guez-G_omez, F.J. and Santillan, R. Multicomponent synthesis and evaluation of new 1, 2, 3-triazole derivatives of dihydropyrimidinones as acidic corrosion inhibitors for steel", Molecules, 21(2), p. 250 (2016). 7. Saraei, M., Ghasemi, Z., Dehghan, G., Hormati, M. and Ojaghi, K. Synthesis of some novel 1,2,3- triazole derivatives containing kojic acid moiety and evaluation for their antioxidant activity", Monatsh. Chem., 148(5), pp. 917-923 (2017). 8. Huisgen, R. 1, 3-dipolar cycloadditions. Past and future", Angew. Chem. Int. Ed., 2(10), pp. 565-598 (1963). 9. Rostovtsev, V.V., Green, L.G., Fokin, V.V., and Sharpless, K.B. A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective ligation" of azides and terminal alkynes", Angew. Chem. Int. Ed., 41(14), pp. 2596-2599 (2002). 10. Wang, Y., Liu, J., and Xia, C. Insights into supported copper(II)-catalyzed azide-alkyne cycloaddition in water", Adv. Synth. Catal., 353(9), pp. 1534-1542 (2011). 11. Slimi, R., Kalhor-Monfared, S., Plancq, B., and Girard, C. A-21.CuI as a catalyst for huisgen's reaction: about iodination as a side-reaction", Tetrahedron Lett., 56(29), pp. 4339-4344 (2015). 12. Kim, J.H. and Kim, S. Phase transfer agent assisted biphasic CuAAC reaction", RSC Adv., 4(50), pp. 26516-26523 (2014). 13. Intrieri, D., Zardi, P., Caselli, A., and Gallo, E. Organic azides: energetic reagents for the intermolecular amination of C-H bonds", Chem. Commun., 50(78), pp. 11440-11453 (2014). 14. Wang, D., Zhao, M., Liu, X., Chen, Y., Li, N., and Chen, B. Quick and highly e_cient copper-catalyzed cycloaddition of organic azides with terminal alkynes", Org. Biomol. Chem., 10(2), pp. 229-231 (2012). 15. Ji, P., Atherton, J.H., and Page, M.I. Copper catalysed azide-alkyne cycloaddition (CuAAC) in liquid ammonia", Org. Biomol. Chem., 10(39), pp. 7965-7969 (2012). 1494 H. Tourani et al./Scientia Iranica, Transactions C: Chemistry and ... 26 (2019) 1485{1496 16. Gonda, Z. and Novak, Z. Highly active coppercatalysts for azide-alkyne cycloaddition", Dalton Trans., 39(3), pp. 726-729 (2010). 17. Bai, S.Q., Jiang, L., Zuo, J.L., and Hor, T.S.A. Hybrid NS ligands supported Cu(i)/(ii) complexes for azide-alkyne cycloaddition reactions", Dalton Trans., 42(31), pp. 11319-11326 (2013). 18. Nasir Baig, R.B. and Varma, R.S. A highly active magnetically recoverable nano ferrite-glutathionecopper (nano-FGT-Cu) catalyst for huisgen 1,3-dipolar cycloadditions", Green Chem., 14(3), pp. 625-632 (2012). 19. Masteri-Farahani, M. and Modarres, M. Encapsulation of Keggin-type phosphotungstic acid into the mesopores of SBA-16 as a reusable heterogeneous catalyst for the epoxidation of ole_ns", Sci. Iran., 24(6), pp. 2993-3001 (2017). 20. Bamoniri, A. and Yaghmaeiyan-Mahabadi, N. Nano kaolin-SO3H as a new e_cient and reusable catalyst for one-pot synthesis of 2,4,5-trisubstituted imidazoles under solvent-free conditions", Sci. Iran., 25(3), pp. 1344-1353 (2018). 21. Kantam, M.L., Jaya, V.S., Sreedhar, B., Rao, M.M., and Choudary, B.M. Preparation of alumina supported copper nanoparticles and their application in the synthesis of 1,2,3-triazoles", J. Mol. Catal. A: Chem., 256(1-2), pp. 273-277 (2006). 22. Bagherzadeh, M., Mahmoudi, H., Amini, M., Gautam, S., and Chae, K.H. SBA-15-supported copper (II) complex: an e_cient heterogeneous catalyst for azidealkyne cycloaddition in water", Sci. Iran., 25(3), pp. 1335-1343 (2018). 23. Pourjavadi, A., Tajbakhsh, M., Farhang, M., and Hosseini, S.H. Copper-loaded polymeric magnetic nanocatalysts as retrievable and robust heterogeneous catalysts for click reactions", New J. Chem., 39(6), pp. 4591-4600 (2015). 24. Zohreh, N., Hosseini, S.H., Pourjavadi, A., and Bennett, C. Immobilized copper(II) on nitrogenrich polymer-entrapped Fe3O4 nanoparticles: a highly loaded and magnetically recoverable catalyst for aqueous click chemistry", Appl. Organomet. Chem., 30(2), pp. 73-80 (2016). 25. Presolski, S. Protein sca_olds: Design, synthesis, and applications", in Methods in Molecular Biology, 1th Edn., pp. 187-193, Humana Press, Springer, New York (2018). 26. Masuyama, Y., Yoshikawa, K., Suzuki, N., Hara, K., and Fukuoka, A. Hydroxyapatite-supported copper(II)-catalyzed azide-alkyne [3+2] cycloaddition with neither reducing agents nor bases in water", Tetrahedron Lett., 52(51), pp. 6916-6918 (2011). 27. Shojaei, A.F., Tabatabaeian, K., and Zebardast, M. Ferric ion modi_ed nano-MOF-5 synthesized by direct mixing approach: A highly e_cient adsorbent for methylene blue dye", Sci. Iran., 25(3), pp. 1323-1334 (2018). 28. Liu, J., Chen, L., Cui, H., Zhang, J., Zhang, L., and Su, C.Y. Applications of metal-organic frameworks in heterogeneous supramolecular catalysis", Chem. Soc. Rev., 43(16), pp. 6011-6061 (2014). 29. Zhu, Q.L. and Xu, Q. Metal-organic framework composites", Chem. Soc. Rev., 43(16), pp. 5468-5512 (2014). 30. Panahi, L., Naimi-Jamal, M.R., Mokhtari, J., and Morsali, A. Mechanochemically synthesized nano-porous metal-organic framework Cu2(BDC)2 (DABCO): An e_cient heterogeneous catalyst for preparation of carbamates", Microporous Mesoporous Mater., 244, pp. 208-217 (2017). 31. Seki, K. and Mori, W. Syntheses and characterization of microporous coordination polymers with open frameworks", J. Phys. Chem. B, 106(6), pp. 1380-1385 (2002). 32. Alavi, M.A. and Morsali, A. Ultrasound assisted synthesis of [Cu2(BDC)2(dabco)].2DMF.2H2O nanostructures in the presence of modulator; new precursor to prepare nano copper oxides", Ultrason. Sonochem., 21(2), pp. 674-680 (2014). 33. Ali, A.A., Chetia, M., Saikia, B., Saikia, P.J., and Sarma, D. AgN(CN)2/DIPEA/H2O-EG: a highly e_cient catalytic system for synthesis of 1,4- disubstituted-1,2,3 triazoles at room temperature", Tetrahedron Lett., 56(43), pp. 5892-5895 (2015). 34. Tale, R.H., Gopula, V.B., and Toradmal, G.K. 'Click' ligand for 'click' chemistry: (1-(4-methoxybenzyl)- 1-H-1,2,3-triazol-4-yl)methanol (MBHTM) accelerated copper-catalyzed [3+2] azide-alkyne cycloaddition (CuAAC) at low catalyst loading", Tetrahedron Lett., 56(43), pp. 5864-5869 (2015). 35. Wang, Q.Y., Sheng, W.S., Sheng, S.R., Li, Y., and Cai, M.Z. Click chemistry on polymer support: synthesis of 1-vinyl- and 1-allyl-1,2,3-triazoles via selenium linker", Synth. Commun., 44(1), pp. 59-67 (2014). 36. Li, X., Chen, X., Jiang, Y., Chen, S., Qu, L., Qu, Z., Yuan, J., and Shi, H. Highly e_cient ultrasonicassisted CuCl-catalyzed 1,3-dipolar cycloaddition reactions in water: synthesis of coumarin derivatives linked with 1,2,3-triazole moiety", J. Heterocycl. Chem., 53(5), pp. 1402-1411 (2016). 37. Pericherla, K., Khedar, P., Khungar, B., and Kumar, A. Click chemistry inspired structural modi_cation of azole antifungal agents to synthesize novel 'drug like' molecules", Tetrahedron Lett., 53(50), pp. 6761-6764 (2012). 38. Nemati, F., Heravi, M.M., and Elhampour, A. Magnetic nano-Fe3O4@TiO2/Cu2O core-shell composite: an e_cient novel catalyst for the regioselective synthesis of 1,2,3-triazoles using a click reaction", RSC Adv., 5(57), pp. 45775-45784 (2015). H. Tourani et al./Scientia Iranica, Transactions C: Chemistry and ... 26 (2019) 1485{1496 1495 39. Hosseinzadeh, R., Abolfazli, M.K., Mohseni, M., Mohadjerani, M., and Lasemi, Z. E_cient synthesis and antibacterial activities of some novel 1,2,3-triazoles prepared from propargylic alcohols and benzyl azides", J. Heterocycl. Chem., 51(5), pp. 1298-1305 (2014). 40. Movassagh, B. and Rezaei, N. Polystyrene resinsupported CuI-cryptand 22 complex: a highly e_cient and reusable catalyst for three-component synthesis of 1,4-disubstituted 1,2,3-triazoles under aerobic conditions in water", Tetrahedron, 70(46), pp. 8885-8892 (2014). 41. Doiron, J., Soultan, A.H., Richard, R., Tour_e, M.M., Picot, N., Richard, R., _Cuperlovi_c-Culf, M., Robichaud, G.A., and Touaibia, M. Synthesis and structure-activity relationship of 1- and 2-substituted- 1,2,3-triazole letrozole-based analogues as aromatase inhibitors", Eur. J. Med. Chem., 46(9), pp. 4010-4024 (2011). 42. Joshi, N. and Banerjee, S. PVP coated copper-iron oxide nanocomposite as an e_cient catalyst for click reactions", Tetrahedron Lett., 56(28), pp. 4163-4169 (2015). 43. Fletcher, J.T., Keeney, M.E., and Walz, S.E. 1- allyl-and 1-benzyl-3-methyl-1, 2, 3-triazolium salts via tandem click transformations", Synthesis, 2010(19), pp. 3339-3345 (2010). 44. Sun, S., Bai, R., and Gu, Y. From waste biomass to solid support: lignosulfonate as a cost-e_ective and renewable supporting material for catalysis", Chem. - Eur. J., 20(2), pp. 549-558 (2014). 45. Mandal, B.H., Rahman, M.L., Yuso_, M.M., Chong, K.F., and Sarkar, S.M. Bio-waste corn-cob cellulose supported poly (hydroxamic acid) copper complex for huisgen reaction: waste to wealth approach", Carbohydr. Polym., 156, pp. 175-181 (2017). 46. Pourjavadi, A., Hosseini, S.H., Zohreh, N., and Bennett, C. Magnetic nanoparticles entrapped in the cross-linked poly (imidazole/imidazolium) immobilized Cu (II): an e_ective heterogeneous copper catalyst", RSC Adv., 4(87), pp. 46418-46426 (2014). 47.  Oz_cubuk_cu, S., Ozkal, E., Jimeno, C. and Pericas, M.A. A highly active catalyst for huisgen 1, 3-dipolar cycloadditions based on the tris (triazolyl) methanol- Cu (I) structure", Org. Lett., 11(20), pp. 4680-4683 (2009). 48. Wan, L. and Cai, C. Multicomponent synthesis of 1, 2, 3-triazoles in water catalyzed by silica-immobilized NHC-Cu (I)", Catal. Lett., 142(9), pp. 1134-1140 (2012). 49. Lai, B., Huang, Z., Jia, Z., Bai, R., and Gu, Y. Silica-supported metal acetylacetonate catalysts with a robust and exible linker constructed by using 2- butoxy-3, 4-dihydropyrans as dual anchoring reagents and ligand donors", Catal. Sci. Technol., 6, pp. 1810- 1820 (2016). 50. Zhang, C., Huang, B., Chen, Y., and Cui, D.M. Porous copper catalyzed click reaction in water", New J. Chem., 37(9), pp. 2606-2609 (2013). 51. Liu, J., Liu, M., Yue, Y., Yao, M., and Zhuo, K. Environmental friendly azide-alkyne cycloaddition reaction of azides, alkynes, and organic halides or epoxides in water: e_cient click" synthesis of 1, 2, 3-triazole derivatives by Cu catalyst", Chin. J. Chem., 30(3), pp. 644-650 (2012). 52. B_en_eteau, V., Olmos, A., Boningari, T., Sommer, J., and Pale, P. Zeo-click synthesis: CuI-zeolitecatalyzed one-pot two-step synthesis of triazoles from halides and related compounds", Tetrahedron Lett., 51(28), pp. 3673-3677 (2010). 53. Purnima, K., Sreenu, D., Bhasker, N., Nagaiah, K., Lingaiah, N., Subba Reddy, B., and Yadav, J. Copper salt of 12-tungstophosphoric acid: an e_cient and reusable heteropoly acid for the click chemistry", Chin. J. Chem., 31(4), pp. 534-538 (2013). 54. Worell, B.T., Malik, J.A., and Fokin, V.V. Direct evidence of a dinuclear copper intermediate in Cu(I)- catalyzed azide-alkyne cyScience, 340, pp. 457-460 (2013).