Open Journal Systems

Synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by Perchlorated Zirconia (HClO4/ZrO2) nanoparticles as a novel solid acid catalyst

Seyed Yousef Mosavian

Abstract

Zirconia was synthesized in nanosize by sol-gel method and perchlorated zirconia (HClO4/ZrO2) with various calcination temperatures were prepared and characterized by XRD, FTIR and SEM techniques. The catalyst acidity characters, including the acidicstrength and the total number of acid sites were determined by potentiometric titration. The catalytic performance experiments show that the HClO4/ZrO2 with calcination temperature of 300 °C has the best catalytic activity. 2,3-Dihydroquinazolin-4(1H)-ones were

prepared in good to excellent yields via condensation reaction of oaminobenzamide and various types of aldehydes and ketones in the presence of HClO4/ZrO2 nanoparticles as an efficient solid acid catalyst. The catalyst is reusable with moderate loss in activity.


Full Text:

PDF

References

Jin Zhang; Jiawen Zhao; Liangpeng Wang, Design, synthesis and docking studies of some spiro-oxindole dihydroquinazolinones as antibacterial agents, Tetrahedron Lett. 72 (2016) 936-943.

A. Kamal; E.V. Bharathi; J.S. Reddy; M.J. Ramaiah; D. Dastagiri, Synthesis and biological evaluation of 3,5-diaryl

isoxazoline/isoxazole linked 2,3-dihydroquinazolinone hybrids as anticancer agents, J. Med.Chem. 46 (2011) 691-703.

K. Hemalatha; G. Madhumitha; Lokesh Ravi, Binding mode of dihydroquinazolin ones with lysozyme and its antifungal activity against Aspergillus species, Journal of Photochemistry and Photobiology B: Bi-ology.161 (2016)71-79.

Kung, P.-P.; Casper, M.D.; Cook, K.L.; Wilson-Lingardo, L.; Risen, L.M.; Vickers, T.A.; Ranken, R.; Blyn, L.B.; Wyatt, J.R.; Cook, P.D., et al, Structure−Activity Relationships of Novel 2-Substituted Quina-zoline Antibacterial Agents, J. Med. Chem. 42 (1999) 4705-4713.

Dandia, A.; Singh, R.; Sarawgi, P, Green chemical multi-component one-pot synthesis of fluorinated 2,3-disubstituted quinazolin-4(3H)-ones under solvent-free conditions and their anti-fungal activity, J. Fluorine Chem. 126 (2005) 307-312.

Xia, Y.; Yang, Z.-Y.; Hour, M.-J.; Kuo, S.-C.; Xia, P.; Bastow, et al, Antitumor Agents. Part 204: Synthesis and Biological Evaluation of Substituted 2-Aryl Quinazolinones,Bioorganic & Medicinal Chemistry Letters. 11 (2001) 1193-1196.

Lee, S.H.; Jung, S.Y.; Park, H.A.; Kang, H.B.; Kim, J.; Choo, D.J.; Handforth, A.; Lee, J.Y, Jpn. J. Pharmacol. 2001, 85, 339.

Jiang, J.B.; Hesson, D.P.; Dusak, B.A.; Dexter, D.L.; Kang, G.J.; Hamel, E, Synthesis and biological evaluation of 2-styrylquinazolin-4(3H)-ones, a new class of antimitotic anticancer agents which inhibit tubulin polymerization, J. Med. Chem. 33 (1990) 1721-1728.

Abdollahi-Alibeik, M.; Shabani, E, Synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by zirco-nium (IV) chloride as a mild and efficient catalyst, Chin. Chem. Lett. 22 (2011) 1163-1166.

Davoodnia, A.; Allameh, S.; Fakhari, A.R.; Tavakoli-Hoseini, N, Highly efficient solvent-free synthesis of quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones using tetrabutylammonium bromide as novel ionic liquid catalyst, Chin. Chem. Lett. 21 (2010) 550-553.

Rostami, A.; Tavakoli, A, Sulfamic acid as a reusable and green catalyst for efficient and simple syn-thesis of 2-substituted-2,3-dihydroquinazolin-4(1H)-ones in water or methanol, Chin. Chem. Lett. 22 (2011) 1317-1320.

Zong, Y.; Zhao, Y.; Luo, W.; Yu, X.H.; Wang, J.K.; Pan, Y, Highly efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropoly acids in water, Chin. Chem. Lett. 21 (2010) 778-781.

Junke Wang; Yingxiao Zong, Poly(4-vinylpyridine) supported acidic ionic liquid: A novel solid catalyst for the efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones under ultrasonic irradiation, Ultrasonics Sonochemistry. 21 (2014) 29–34.

Karimi-Jaberi, Z; Zarei, L, Synthesis of Coumarins and 2,3-dihydroquinazolin-4(1H)-ones Using Trichloroacetic Acid as a Catalyst, Acta Chim Slov. 60 (2013) 178–183.

Ghashang, M.; Mansoor, S.S.; Aswin, K, Synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by succinimide-N-sulfonic acid as a mild and efficient catalyst, Research on Chemical Intermediates. 41 (2015) 3447–3460.

Weizuo Li; Zhongkui Zhao, Morphology effect of zirconia support on the catalytic performance of supported Ni catalysts for dry reforming of methane, Chinese Journal of Catalysis. 37 (2016) 2122–2133.

Ashkarran A.A., Aghigh S.M., Ahmadi Afshar S.A., Kavianipour M., Ghoranneviss M., Synthesis and Characterization of ZrO2 Nanoparticles by Arc Discharge Method in Water, Metal-Organic, and Nano-Metal Chemistry. 41 (2011) 425-428.

Zhang X, He DH, Zhang QJ, Xu BQ, Zhu QM, Comparative studies on direct conversion of methane to methanol/formaldehyde over La–Co–O and ZrO2 supported molybdenum oxide catalysts, Top Catal. 32 (2005) 215–223.

Li J, Chen JL, Song W, Liu JL, Shen WJ, Influence of zirconia crystal phase on the catalytic perfor-mance of Au/ZrO2 catalysts for low-temperature water gas shift reaction, Appl Catal A. 334 (2008) 321–329.

Xu S, Wang XL, Highly active and coking resistant Ni/CeO2–ZrO2 catalyst for partial oxidation of methane, Fuel. 84 (2005) 563–567.

B. Jiang, B. Deng, Z. Zhang, Z. Wu, X. Tang, S. Yao, H. Lu, Effect of Zr addition on the low-temperature SCR activity and SO2 tolerance of Fe–Mn/Ti catalysts, J.Phys. Chem. C 118 (2014) 14866–14875.

Bampenrat, A.; Meeyoo, V.; Kitiyanan, B.; Rangsunvigit, P, Catalytic oxidation of naphthalene over CeO2–ZrO2 mixed oxide catalysts, Catal. Commun. 9 (2008) 2349-2352.

Liu, S.; Zhang, X.; Li, J.; Zhao, N, Preparation and application of stabilized mesoporous MgO–ZrO2 solid base, Catal. Commun. 9 (2008) 1527-1532.

Fujiwara, M.; Yamamura, I.; Nishiyama, M.; Shiokawa, K, Bisphenol A Imprinted SiO2‐ZrO2 Mixed Oxide Materials Prepared by Acetic Anhydride Sol‐Gel Method, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry. 37 (2007) 771-777.

Abdollahi-Alibeik, M.; Mohammadpoor-Baltork, I.; Zaghaghi, Z, Efficient synthesis of 1,5-benzodiazepines catalyzed by silica supported 12-tungstophosphoric acid, Catal. Commun. 9 (2008) 2496-2502.

Abdollahi-Alibeik, M.; Pouriayevali, M, Nanosized MCM-41 supported protic ionic liquid as an effi-cient novel catalytic system for Friedlander synthesis of quinolines, Catal. Commun. 22 (2012) 13-18.

Mohammadpoor-Baltork, I.; Abdollahi-Alibeik, M, Mild, efficient, and chemoselective dehydrogena-tion of 2-imidazolines, bis-imidazolines, and N-substituted-2-imidazolines with potassium permanganate supported on montmorillonite K-10, Can. J. Chem. 83 (2005) 110-114.

Mishra, H.K.; Parida, K.M, Effect of perchlorate ion on the textural and catalytic activity of zirconia, Appl. Catal. A: Gen. 184 (1999) 219-229.


DOI: http://dx.doi.org/10.18063/nn.v0i0.449
(62 Abstract Views, 52 PDF Downloads)

Refbacks

  • There are currently no refbacks.


Copyright (c) 2018 Nanoscience and Nanotechnology