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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

MoO3 Nanoparticles as an Efficient Catalyst for the Synthesis of Pyrazoles in Aqueous-alcoholic Medium at Room Temperature

Author(s): Sonatai Patil*, Ananda Mane and Savita Dhongade-Desai

Volume 17, Issue 9, 2020

Page: [694 - 703] Pages: 10

DOI: 10.2174/1570178617666191127103433

Price: $65

Abstract

We have successfully explored the potential MoO3 nanoparticles as a heterogeneous catalyst for the cyclocondensation of hydrazines/hydrazides with 1,3-dicarbonyl compound in aqueousalcoholic medium at room temperature. The present method has been developed using green chemistry measures and offers a range of N-substituted pyrazoles with moderate to excellent yields. Utilization of non-toxic catalyst, wide substrate scope and environmentally benign reaction medium are the important features of the developed protocol. Interestingly, MoO3 nanocatalyst can easily be recovered from the reaction mixture and showed excellent reusability with a modest change in product yield. We have reported herein the synthetic pathway with less disastrous effect in the atmosphere.

Keywords: Pyrazoles, MoO3 nanoparticles, cosolvent, Aqueous alcoholic medium, heterogeneous catalysis, reusability.

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[1]
Pan, Y.; Shen, X.; Yao, L.; Bentalib, A.; Peng, Z. Catalysts, 2018, 8, 478.
[http://dx.doi.org/10.3390/catal8100478]
[2]
Wang, F.; Ueda, W. Chem. Eur. J., 2009, 15(3), 742-753.
[http://dx.doi.org/10.1002/chem.200801153] [PMID: 19035603]
[3]
Said, M.S.; Khandare, L.; Shinde, S.S. Tetrahedron Lett., 2017, 58, 59-62.
[http://dx.doi.org/10.1016/j.tetlet.2016.11.099]
[4]
Pourshojaei, Y.; Jadidi, M.; Eskandari, K.; Foroumadi, A.; Asadipour, A. Res. Chem. Intermed., 2018, 44, 4195-4212.
[http://dx.doi.org/10.1007/s11164-018-3363-7]
[5]
Kumar, K.H.; Paricharak, S.; Mohan, C.D.; Bharathkumar, H.; Nagabhushana, G.P.; Rajashekar, D.K.; Chandrappa, G.T.; Bender, A. Basappa; Rangappa, K.S. New J. Chem., 2016, 40, 2189-2199.
[http://dx.doi.org/10.1039/C5NJ02729B]
[6]
Dighore, N.R.; Anandgaonker, P.L.; Gaikwad, S.T.; Rajbhoj, A.S. Mater. Sci-Poland, 2015, 33, 163-168.
[http://dx.doi.org/10.1515/msp-2015-0024]
[7]
(a)Kuwahara, Y.; Furuichi, N.; Seki, H.; Yamashita, H. J. Mater. Chem. A, 2017, 5, 18518-18526.
[http://dx.doi.org/10.1039/C7TA06288E]
(b)Chandra, P.; Doke, D.S.; Umbarkar, S.B.; Biradar, A.V. J. Mater. Chem. A, 2014, 2, 19060-19066.
[http://dx.doi.org/10.1039/C4TA03754E]
(c)Fernandes, C.I.; Capelli, S.C.; Vaz, P.D.; Nunes, C.D. Appl. Catal. A Gen., 2015, 504, 344-350.
[http://dx.doi.org/10.1016/j.apcata.2015.02.027]
[8]
Malakooti, R.; Shafie, S.; Hosseinabadi, R.; Heravi, M.M.; Zakeri, M.; Mohammadi, N. Synth. React. Inorg. M., 2014, 44, 1401-1406.
[http://dx.doi.org/10.1080/15533174.2013.809740]
[9]
Manivel, A.; Lee, G-J.; Chen, C-Y.; Chen, J-H.; Ma, S-H.; Horng, T-L.; Wu, J. J. Mater. Res. Bull., 2015, 62, 184-191.
[http://dx.doi.org/10.1016/j.materresbull.2014.11.016]
[10]
Simon, M-O.; Li, C-J. Chem. Soc. Rev., 2012, 41, 1415-1427.
[http://dx.doi.org/10.1039/C1CS15222J]
[11]
(a)Cheng, T.; Zhang, D.; Li, H.; Liu, G. Green Chem., 2014, 16, 3401-3427.
[http://dx.doi.org/10.1039/C4GC00458B]
(b)Alizadeh, A.; Khodaei, M.M.; Beygzadeh, M.; Kordestani, D.; Feyzi, M. Bull. Korean Chem. Soc., 2012, 33, 2546-2552.
[http://dx.doi.org/10.5012/bkcs.2012.33.8.2546]
(c)Du, Q.; Zhang, W.; Ma, H.; Zheng, J.; Zhou, B.; Li, Y. Tetrahedron, 2012, 68, 3577-3584.
[http://dx.doi.org/10.1016/j.tet.2012.03.008]
(d)Wang, Y.; Jiang, P.; Zhang, W. Zheng. J. Appl. Surf. Sci., 2013, 270, 531-538.
[http://dx.doi.org/10.1016/j.apsusc.2013.01.082]
[12]
(a)Davies, D.T. Aromatic Heterocyclic Chemistry; Oxford, 1997, pp. 28-29.
(b)Kiyani, H.; Albooyeh, F.; Fallahnezhad, S. J. Mol. Struct., 2015, 1091, 163-169.
[http://dx.doi.org/10.1016/j.molstruc.2015.02.069]
(c)Ansari, A.; Ali, A.; Asif, M. Shamsuzzaman. New J. Chem., 2017, 41, 16-41.
[http://dx.doi.org/10.1039/C6NJ03181A]
[13]
(a)Karrouchi, K.; Radi, S.; Ramli, Y.; Taoufik, J.; Mabkhot, Y.N.; Al-aizari, F.A.; Ansar, M. Molecules, 2018, 23, 134.
[http://dx.doi.org/10.3390/molecules23010134]
(b)Naim, M.J.; Alam, O.; Nawaz, F.; Alam, M.J. Alam. P. J. Pharm. Bioall. Sci., 2016, 8(1), 2-17.
[14]
Fiorucci, S.; Santucci, L.; Distrutti, E. Dig. Liver Dis., 2007, 39(12), 1043-1051.
[http://dx.doi.org/10.1016/j.dld.2007.09.001] [PMID: 17997373]
[15]
(a)Lin, C.; Wang, H.; Wang, Y.; Cheng, Z. Talanta, 2010, 81(1-2), 30-36.
[http://dx.doi.org/10.1016/j.talanta.2009.11.032] [PMID: 20188883]
(b)Bose, R.; Murty, D.S.R.; Chakrapani, G. J. Radioanal. Nucl. Chem., 2005, 265, 115-122.
[http://dx.doi.org/10.1007/s10967-005-0795-5]
[16]
Karci, F.; Karci, F.; Demircali, A.; Yamac, M. J. Mol. Liq., 2013, 187, 302-308.
[http://dx.doi.org/10.1016/j.molliq.2013.08.005]
[17]
Willy, B.; Müller, T.J.J. Org. Lett., 2011, 13(8), 2082-2085.
[http://dx.doi.org/10.1021/ol2004947] [PMID: 21417307]
[18]
Gao, X.C.; Cao, H.; Zhang, L.Q.; Zhang, B.W.; Cao, Y.; Huang, C.H. J. Mater. Chem., 1999, 9, 1077-1080.
[http://dx.doi.org/10.1039/a900276f]
[19]
Wang, M.; Zhang, J.; Liu, J.; Xu, C.; Ju, H. J. Lumin., 2002, 99, 79-83.
[http://dx.doi.org/10.1016/S0022-2313(01)00204-6]
[20]
Burschka, J.; Kessler, F.; Nazeeruddin, M.K.; Gratzel, M. Chem. Mater., 2013, 25, 2986-2990.
[http://dx.doi.org/10.1021/cm400796u]
[21]
Kauhanka, U.M.; Kauhanka, M.M. Liq. Cryst., 2006, 33, 121-127.
[http://dx.doi.org/10.1080/02678290500429976]
[22]
Chou, P-T.; Chi, Y. Chem. Eur. J., 2007, 13(2), 380-395.
[http://dx.doi.org/10.1002/chem.200601272] [PMID: 17146830]
[23]
(a)Ye, C.; Gard, G.L.; Winter, R.W.; Syvret, R.G.; Twamley, B.; Shreeve, J.M. Org. Lett., 2007, 9(19), 3841-3844.
[http://dx.doi.org/10.1021/ol701602a] [PMID: 17715932 ]
(b)Gondek, E. Mater. Lett., 2013, 112, 94-96.
[http://dx.doi.org/10.1016/j.matlet.2013.08.128]
[24]
Polshettiwar, V.; Varma, R.S. Tetrahedron Lett., 2008, 49, 397-400.
[http://dx.doi.org/10.1016/j.tetlet.2007.11.017]
[25]
Chandak, H.S.; Lad, N.P.; Dange, D.S. Green Chem. Lett. Rev., 2012, 5, 135-138.
[http://dx.doi.org/10.1080/17518253.2011.585352]
[26]
Kidwai, M.; Jain, A.; Poddar, R. J. Organomet. Chem., 2011, 696, 1939-1944.
[http://dx.doi.org/10.1016/j.jorganchem.2010.09.012]
[27]
Chen, X.; She, J.; Shang, Z.; Wu, J.; Wu, H.; Zhang, P. Synthesis, 2008, 21, 3478-3486.
[28]
Sreekumar, R.; Padmakumar, R. Synth. Commun., 1998, 28, 1661-1665.
[http://dx.doi.org/10.1080/00397919808006870]
[29]
Nasseri, M.A.; Salimi, M.; Esmaeili, A.A. RSC Adv., 2014, 4, 61193-61199.
[http://dx.doi.org/10.1039/C4RA11440J]
[30]
Teimouri, A.; Chermahini, A.N.; Ghorbanian, L. Iran. J. Catal., 2014, 4, 9-15.
[31]
Barge, M.; Kamble, S.; Kumbhar, A.; Rashinkar, G.; Salunkhe, R. Monatsh. Chem., 2013, 144, 1213-1218.
[http://dx.doi.org/10.1007/s00706-013-0944-4]
[32]
da Silva, M.J.V.; Poletto, J.; Jacomini, A.P.; Pianoski, K.E.; Gonçalves, D.S.; Ribeiro, G.M. de S Melo, S.M.; Back, D.F.; Moura, S.; Rosa, F.A. J. Org. Chem., 2017, 82(23), 12590-12602.
[http://dx.doi.org/10.1021/acs.joc.7b02361] [PMID: 29094945]
[33]
Texier-Boullet, F.; Klein, B.; Hamelin, J. Synthesis, 1986, 5, 409-411.
[http://dx.doi.org/10.1055/s-1986-31655]
[34]
Shetty, M.R.; Samant, S.D. Synth. Commun., 2012, 42, 1411-1418.
[http://dx.doi.org/10.1080/00397911.2010.540365]
[35]
Xiong, W.; Chen, J.X.; Liu, M-C.; Ding, J.C.; Wu, H.Y.; Su, W.K. J. Braz. Chem. Soc., 2009, 20, 367-374.
[http://dx.doi.org/10.1590/S0103-50532009000200023]
[36]
Chen, X.; She, J.; Shang, Z-C.; Wu, J.; Zhang, P. Synth. Commun., 2009, 39, 947-957.
[http://dx.doi.org/10.1080/00397910802441551]
[37]
Yang, G.P.; He, X.; Yu, B.; Hu, C.W. Appl. Organomet. Chem., 2018, 32e4532
[http://dx.doi.org/10.1002/aoc.4532]
[38]
Curini, M.; Rosati, O.; Campagna, V.; Montanari, F.; Cravotto, G.; Boccalini, M. Synlett, 2005, 19, 2927-2930.
[http://dx.doi.org/10.1055/s-2005-921904]
[39]
(a)Vaddula, B.R.; Varma, R.S.; Leazer, J. Tetrahedron Lett., 2013, 54, 1538-1541.
(b)Polshettiwar, V.; Varma, R.S. Tetrahedron, 2010, 66, 1091-1097.
[http://dx.doi.org/10.1016/j.tet.2009.11.015]
[40]
(a)Patil, S.; Mane, A.; Dhongade-Desai, S. J. Iran. Chem. Soc., 2019, 16, 1665 -1675.
[http://dx.doi.org/10.1007/s13738-019-01640-3]
(b)Patil, S.; Mane, A.; Dhongade-Desai, S. Chem. Sci. Rev. Lett., 2018, 7, 732-740.
(c)Mane, A.H.; Patil, A.D.; Kamat, S.R.; Salunkhe, R.S. ChemistrySelect, 2018, 3, 6454-6458.
[http://dx.doi.org/10.1002/slct.201800677]
(d)Mane, A.; Lohar, T.; Salunkhe, R. Tetrahedron Lett., 2016, 57, 2341-2346.
[http://dx.doi.org/10.1016/j.tetlet.2016.04.057]
(e)Mane, A.; Salokhe, P.; More, P.; Salunkhe, R. J. Mol. Catal., B Enzym., 2015, 121, 75-81.
[http://dx.doi.org/10.1016/j.molcatb.2015.05.020]
[41]
Klinbumrung, A.; Thongtem, T.; Thongtem, S. J. Nanomater., 2012, p. 1-5.
[42]
Desai, N.; Mali, S.; Kondalkar, V.; Mane, R.; Hong, C.; Bhosale, P. J. Nanomed. Nanotechnol., 2015, 6(6), p. 1-10.
[http://dx.doi.org/10.4172/2157-7439.1000338]

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