Abstract
Copper (II) acetate is covalently anchored onto the surface of chemically modified starch and the resultant heterogeneous catalyst was investigated for the regioselective synthesis of 1,4-disubstituted-1,2,3-triazoles via Huisgen 1,3-dipolar cycloaddition reaction between terminal alkynes, benzyl/allyl/alkyl halides and NaN3 in distilled water at room temperature. Further, starch functionalized copper (II) acetate could be recovered by simple filtration and recycled up to several consecutive runs without loss of significant activity. The catalyst is characterized by FTIR, thermal analysis, XRD, SEM, TEM, and AAS.
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W. Q. Fan and A. R. Katritzky, 1,2,3 Triazoles. In Comprehensive heterocycle chemistry II; A. R. Katritzky, C. W. Rees, E. F. V. Scriven, Eds.; Pergamon Press: New York, NY, USA, 4, 1, (1996)
A.R. Katritzky, Y. Zhang, S.K. Singh, Heterocycles 60, 1225 (2003)
A.G. Nasibulin, E.I. Kauppinen, D.P. Brown, J.K. Jokiniemi, J. Phys. Chem. B 105, 11067 (2001)
R. Alvarez, S. Velazquez, R. San, S. Aquaro, C.E. De, C.F. Perno, A. Karlsson, J. Balzarini, M.J. Camarasa, J. Med. Chem. 37, 4185 (1994)
S. Velazquez, R. Alvarez, C. Perez, F. Gago, C.E. De, J. Balzarini, J.M. Camarasa, Antiviral Chem. Chemother. 9, 481 (1998)
M. Whiting, J. Muldoon, Y.C. Lin, S.M. Silverman, W. Lindstrom, A.J. Olson, H.C. Kolb, M.G. Finn, B.K. Sharpless, J.H. Elder, V.V. Fokin, Angew. Chem. Int. Ed. 45, 1435 (2006)
A. Brik, J. Muldoon, Y.C. Lin, J.H. Elder, D.S. Goodsell, A.J. Olson, V.V. Fokin, K.B. Sharpless, C.H. Wong, Chem. Bio. Chem. 4, 1246 (2003)
M.J. Genin, D.A. Allwine, D.J. Anderson, M.R. Barbachyn, D.M. Emmert, S.A. Garmon, D.R. Graber, K.C. Grega, J.B. Hester, D.K. Hutchinson, J. Morris, R.J. Reischer, C.W. Ford, G.E. Zurenko, J.C. Hamel, R.D. Schaadt, D. Stapert, B.H. Yagi, J. Med. Chem. 43, 953 (2000)
L.L. Brockunier, E.R. Parmee, H.O. Ok, M.R. Candelore, M.A. Cascieri, L.F. Colwell, L. Deng, W.P. Feeney, M.J. Forrest, G.J. Hom, D.E. MacIntyre, L. Tota, M.J. Wyvratt, M.H. Fisher, A.E. Weber, Bioorg. Med. Chem. Lett. 10, 2111 (2000)
V. Pande, M.J. Ramos, Bioorg. Med. Chem. Lett. 15, 5129 (2005)
P.H. Olesen, A.R. Sorensen, B. Urso, P. Kurtzhals, A.N. Bowler, U. Ehrbar, B.F. Hansen, J. Med. Chem. 46, 3333 (2003)
A. Krasinski, Z. Radic, R. Manetsch, J. Raushel, P. Taylor, B.K. Sharpless, H.C. Kolb, J. Am. Chem. Soc. 127, 6686 (2005)
V.P. Mocharla, B. Colasson, L.V. Lee, S. Roeper, B.K. Sharpless, C.H. Wong, H.C. Kolb, Angew. Chem. Int. Ed. 1, 116 (2005)
R.G. Micetich, S.N. Maiti, P. Spevak, T.W. Hall, S. Yamabe, N. Ishida, M. Tanaka, T. Yamazaki, A. Nakai, K. Ogawa, J. Med. Chem. 30, 1469 (1987)
P. Actor, J.V. Uri, L. Phillips, C.S. Sachs, J.R.G. Zajac, D.A. Berges, G.L. Dunn, J.R.E. Hoover, J.A. Weisbach, J. Antibiot. 28, 594 (1975)
H.C. Kolb, K.B. Sharpless, Drug Discov Today 8, 1128 (2003)
R.K. O’Reilly, M.J. Joralemon, K.L. Wooley, C.J. Hawker, Chem. Mater. 17, 5976 (2005)
D.A. Fleming, C.J. Thode, M.E. Williams, Chem. Mater. 18, 2327 (2006)
J.P. Collman, N.K. Devaraj, T.P.A. Eberspacher, C.E.D. Chidsey, Langmuir 22, 2457 (2006)
R. Huisgen, Proc. Chem. Soc. 357 (1961)
H.C. Kolb, M.G. Finn, K.B. Sharpless, Angew. Chem. Int. Ed. 40, 2004 (2001)
J. Barluenga, C. Valdes, G. Beltran, M. Escribano, F. Aznar, Angew. Chem. Int. Ed. 45, 6893 (2006)
B.C. Boren, S. Narayan, L.K. Rasmussen, L. Zhang, H. Zhao, Z. Lin, G. Jia, V.V. Fokin, J. Am. Chem. Soc. 130, 8923 (2008)
D. Wang, N. Li, M. Zhao, W. Shi, C. Ma, B. Chen, Green Chem. 12, 2120 (2010)
M. Liu, O. Reiser, Org. Lett. 13, 1102 (2011)
J. Albadia, J. A. Shiranb, A. Mansournezhad, J. Chem. Sci. 147 (2014)
B.S.P.A. Kumar, K.H.V. Reddy, B. Madhav, K. Ramesh, Y.V.D. Nageswar, Tetrahedron Lett. 53, 4595 (2012)
R.B.N. Baig, R.S. Varma, Green Chem. 15, 1839 (2013)
N. Aflak, H.B.E. Ayouchia, L. Bahsis, H. Anane, R. Laamari, A. Pascual-Alvarez, D. Armentano, S.-E. Stirib, Polyhedron 170, 630 (2019)
J.-C. Castillo, N.-F. Bravo, L.-V. Tamayo, P.-D. Mestizo, J. Hurtado, M. Macias, J. Portilla, ACS Omega 5, 30148 (2020)
H. Lee, J.K. Lee, S.-J. Min, H. Seo, Y. Lee, H. Rhee, J. Org. Chem. 83, 4805 (2018)
M. Rajabi, J. Albadi, A. Momeni, Res. Chem. Intermed. 46, 3879 (2020)
A.G. Samuel, B. Jebasingh, ChemistrySelect 5, 645 (2020)
A. Khoshnoud, A. Pourali, Org. Prep. Proced. Int. 53, 1 (2021)
P. Saini, G. Singh, G. Kaur, J. Singh, H. Singh, Mol. Catal. 504, 111432 (2021)
X. Chen, W. Yao, F. Gao, D. Zheng, Q. Wang, J. Cao, H. Tan, Y. Zhang, J. Renew. Mater. 9, 979 (2021)
P. Kumar, P. Gupta, C. Sharma, Catal. Sci. Technol. 11, 3775 (2021)
P. Gupta, N. Prakash, Y. Ramawat, P. Rajput, A. Fayaz, T.K. Roy, Lett. Org. Chem. 19, 19 (2022)
A. Mahajan, P. Gupta, New J. Chem. 44, 12897 (2020)
A. Mahajan, P. Gupta, Environ. Chem. Lett. 18, 299 (2020)
Z. Gonda, Z. Novak, Dalton Trans. 39, 726 (2010)
S. Kale, S. Kahandal, S. Disale, R. Jayaram, Current. Chem. Lett. 1, 69 (2012)
T. Miao, L. Wang, Synthesis 363 (2008)
K. Kacprzak, Synlett 5, 943 (2005)
C. Girard, E. Onen, M. Aufort, S. Beauviere, E. Samson, J. Herscovici, Org. Lett. 8, 1689 (2006)
A.N. Prasad, B.M. Reddy, E.-Y. Jeong, S.-E. Park, RSC Adv. 4, 29772 (2014)
F. Rezaei, M.A. Amrollahi, R. Khalifeh, Inorg. Chim. Acta 489, 8 (2019)
A. Kumar, S. Verma, D.D. Pathak, J. Environ. Chem. Eng. 9, 105791 (2021)
A. Nunes, L. Djakovitch, L. Khrouz, F.-X. Felpin, V. Dufaud, J. Mol. Catal. A Chem. 437, 15 (2017)
Y. Zhang, Z. Zhang, Y. Chen, Y. Li, Res. Chem. Intermed. 43, 7307 (2017)
F.M. Mogaddam, M. Eslami, S.E. Ayati, ChemistrySelect 2, 11942 (2017)
A. Khoshnoud, A.R. Pourali, Org. Prep. Proced. Int. 53, 509 (2021)
A.K. Sardarian, F. Mohammadi, M. Esmaeilpour, Res. Chem. Intermed. 45, 1437–1456 (2019)
Acknowledgements
We are grateful to SAIF, Punjab University, Chandigarh, for XRD, SEM and TEM; Head, Institute Instrumentation Centre, Indian Institute of Technology, Roorkee for TGA; and SAIF, Nagpur University, Nagpur, for AAS analysis.
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Dr. Princy prepared the manuscript and Dr. Tahira performed the experiments in lab. Pawan Kumar and Bindu Syal revised/modified the manuscript, performed the repeated experiments in the lab as per the directions of Editor/reviewers.
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Gupta, P., Kumar, P., Syal, B. et al. Synthesis of 1,4-disubstituted-1,2,3-triazoles using starch-functionalized copper (II) acetate as a recyclable heterogeneous catalyst in water. Res Chem Intermed 48, 4601–4615 (2022). https://doi.org/10.1007/s11164-022-04829-z
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DOI: https://doi.org/10.1007/s11164-022-04829-z