Abstract
Zirconia supported silica from rice husk (an agricultural waste) has been utilized as a novel and efficient heterogeneous catalyst for the synthesis of bioactive tetrahydro-1-benzopyran derivatives via multicomponent condensation of various aldehydes with dimedone and malononitrile. This protocol offers various advantages such as high yields, simple experimental work-up procedure, short reaction time, no by-products, economic availability, easy purification, and reusability of the catalyst.
Similar content being viewed by others
REFERENCES
Hassankhani, A., Maghsoodlou, M.T., Habibi-Khorassani, S.M., Hosseini-Mahdiabad, H., and Marandi, G., Arkivoc, 2008, vol. 2008, no. 2, p. 134. https://doi.org/10.3998/ark.5550190.0009.215
Bonsignore, L., Loy, G., Secci, D., and Calignano, A., Eur. J. Med. Chem., 1993, vol. 28, p. 517. https://doi.org/10.1016/0223-5234(93)90020-F
Salvi, P.P., Mandhare, A.M., Sartape, A.S., Pawar, D.K., Han, S.H., and Kolekar, S.S., C. R. Chim., 2011, vol. 14, p. 878. https://doi.org/10.1016/j.crci.2011.02.007
Joshi, V.M., Magar, R.L., Throat, P.B., Tekale, S.U., Patil, B.R., Kale, M.P., and Pawar, R.P., Chin. Chem. Lett., 2014, vol. 25, p. 455. https://doi.org/10.1016/j.cclet.2013.12.016
Kiyani, H. and Ghorbani, F., J. Saudi Chem. Soc., 2014, vol. 18, p. 689. https://doi.org/10.1016/j.jscs.2014.02.004
Zhi, H., Lü, C., Zhang, Q., and Luo, J., Chem. Commun., 2009, no. 20, p. 2878. https://doi.org/10.1039/b822481a
Wang, J.-L., Liu, D., Zhang, Z.-J., Shan, S., Han, X., Srinivasula, S.M., Croce, C.M., Alnemri, E.S., and Huang, Z., Proc. Natl. Acad. Sci. U. S. A., 2000, vol. 97, p. 7124. https://doi.org/10.1073/pnas.97.13.7124
Tabatabaeian, K., Heidari, H., Mamaghani, M., and Mahmoodi, N.O., Appl. Organomet. Chem., 2012, vol. 26, p. 56. https://doi.org/10.1002/aoc.1866
Hekmatshoar, R., Majedi, S., and Bakhtiari, K., Catal. Commun., 2008, vol. 9, p. 307. https://doi.org/10.1016/j.catcom.2007.06.016
Rathod, S., Arbad, B., and Lande, M., Chin. J. Catal., 2010, vol. 31, p. 631. https://doi.org/10.1016/S1872-2067(09)60078-4
Balalaie, S., Bararjanian, M., Sheikh-Ahmadi, M., Hekmat, S., and Salehi, P., Synth. Commun., 2007, vol. 37, p. 1097. https://doi.org/10.1080/00397910701196579
Wang, L.M., Shao, J.H., Tian, H., Wang, Y.H., and Liu, B., J. Fluorine Chem., 2006, vol. 127, p. 97. https://doi.org/10.1016/j.jfluchem.2005.10.004
Payá, J., Monzó, J., Borrachero, M., Mellado, A., and Ordoñez, L., Cem. Concr. Res., 2001, vol. 31, p. 227. https://doi.org/10.1016/S0008-8846(00)00466-X
Chen, W.-S., Chang, F.-W., Roselin, L.S., Ou, T.-C., and Lai, S.-C.. J. Mol. Catal. A: Chem., 2010, vol. 318, p. 36. https://doi.org/10.1016/j.molcata.2009.11.005
Adam, F. and Iqbal, A., Chem. Eng. J., 2010, vol. 160, p. 742. https://doi.org/10.1016/j.cej.2010.04.003
Adam, F. and Iqbal, A., Microporous Mesoporous Mater., 2011, vol. 141, p. 119. https://doi.org/10.1016/j.micromeso.2010.10.037
Adam, F. and Iqbal, A., Chem. Eng. J., 2011, vol. 171, p. 1379. https://doi.org/10.1016/j.cej.2011.05.052
Ghattas, M.S., Microporous Mesoporous Mater., 2006, vol. 97, p. 107. https://doi.org/10.1016/j.micromeso.2006.08.012
Adam, F. and Andas, J., J. Colloid Interface Sci., 2007, vol. 311, p. 135. https://doi.org/10.1016/j.jcis.2007.02.083
Nizam, A. and Päsha, M.A., Synth. Commun., 2010, vol. 40, p. 2864. https://doi.org/10.1080/00397910903320654
Bonacin, J.A., Passos, R.R., and Pocrifka, L.A., Mater. Res., 2015, vol. 18, p. 639. https://doi.org/10.1590/1516-1439.009015
Tamaddon, F. and Tavakoli, F., J. Mol. Catal. A: Chem., 2011, vol. 337, p. 52. https://doi.org/10.1016/j.molcata.2011.01.013
Sun, W.-B., Zhang, P., Fan, J., Chen, S.-H., and Zhang, Z.-H., Synth. Commun., 2010, vol. 40, p. 587. https://doi.org/10.1080/00397910903007079
Kaupp, G., Naimi-Jamal, M.R., and Schmeyers, J., Tetrahedron, 2003, vol. 59, p. 3753. https://doi.org/10.1016/S0040-4020(03)00554-4
Mohammadi, A.A., Asghariganjeh, M.R., and Hadadzahmatkesh, A., Arab. J. Chem., 2017, vol. 10, p. S2213. https://doi.org/10.1016/j.arabjc.2013.07.055
Mobinikhaledi, A., Foroughifar, N., and Bodaghi Fard, M.A., Synth. React. Inorg., Met.-Org., Nano-Met. Chem., 2010, vol. 40, p. 179. https://doi.org/10.1080/15533171003629121
Abdollahi-Alibeik, M. and Nezampour, F., React. Kinet. Mech. Catal., 2013, vol. 108, p. 213. https://doi.org/10.1007/s11144-012-0504-7
ACKNOWLEDGMENTS
The authors gratefully acknowledge CHRIST (Deemed to be University) for the support and for the facilities to carry out this project. We are thankful for IISc and St. Joseph’s College, Bangalore, for NMR, SEM, and XRD analysis.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflict of interest.
Rights and permissions
About this article
Cite this article
Mishra, M., Devi, K.R.S., Pinheiro, D. et al. Zirconia Supported on Rice Husk Silica from Biowaste: A Novel, Efficient, and Recoverable Nanocatalyst for the Green Synthesis of Tetrahydro-1-benzopyrans. Russ J Org Chem 56, 1784–1789 (2020). https://doi.org/10.1134/S107042802010019X
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S107042802010019X