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Current Organocatalysis


ISSN (Print): 2213-3372
ISSN (Online): 2213-3380

Research Article

ZIF@ZnTiO3 Nanocomposite as a Reusable Organocatalyst for the Synthesis of 3, 4-dihydropyrano[c]chromene Derivatives

Author(s): Taybeh Farahmand, Saeedeh Hashemian* and Ali Shibani

Volume 6 , Issue 3 , 2019

Page: [248 - 256] Pages: 9

DOI: 10.2174/2213337206666190610094227


Background: Dihydropyrano [3, 2-c]chromenes and their derivatives have great attention for scientists. They have different activities such as biological properties, spasmolytic, diuretic, anticoagulant, anti-cancer, and anti-anaphylactic activity. For these vary biological activities, chromene derivatives have made significant for further progress in medicinal and organic synthesis studies. So, in view of the importance of chromenes, we aimed to synthesis of 3, 4-dihydropyrano [3, 2-c] chromene derivatives. ZIF@ZnTiO3nanocomposite as organocatalyst was used.

Results: An effective and applicable technique was used for preparation of 3, 4-dihydropyrano [3, 2- c] chromene derivatives. Dihydropyrano [c] chromenederivatives were prepared by using ZIF@ZnTiO3compositeas a recyclable catalyst. One-pot three-component reaction of aromatic aldehydes, malononitrile, and 4-hydroxycoumarin was done for synthesis of dihydropyrano [c] chromenederivatives over composite catalyst with excellent yields. The as prepared dihydropyrano [c] chromenederivatives were measured by melting point, FTIR, 1H NMR, and 13C NMR. The nano catalyst could be recycled several times.

Methods: A novel nano catalyst of MOF containing Mn2+ ions and 2- methyl imidazole (ZIF) and zinctitanate (ZIF@ZnTiO3) composite was prepared. The synthesized organocatalyst was studied for preparation of 3, 4-dihydropyrano [3, 2-c] chromene derivatives. One-pot three-component reaction of aromatic aldehydes, malononitrile, and 4-hydroxycoumarin was done for synthesis of dihydropyrano [c] chromene derivatives over composite catalyst with excellent yields. The reaction was optimized.

Conclusion: The organocatalyst composite of consist of ZIF and zinctitanate was prepared. The ZIF@ZnTiO3 was used as catalyst for synthesis of 3, 4-dihydropyrano [3, 2-c] chromene derivatives via one-pot three-component condensations of aromatic aldehydes,malononitrile, and 4 hydroxycoumarin. The results of melting point, FTIR, 1H NMR, 13C NMR also confirmed the formation of high yield of 3, 4-dihydropyrano [3, 2-c] chromene derivatives at short time. The appealing properties of this method are environmentally friendly, mild reaction conditions (low reaction time and high yields of pure products), easy work up and recyclability of reaction catalyst.

Keywords: Chromene, MOF, nanocomposite, organocatalyst, reusable, ZIF@ZnTiO3.

Graphical Abstract
Abdolmohammadi, S. Balalaie, S: Novel and efficient catalysts for the one-pot synthesis of 3,4-dihydropyrano[c]chromene derivatives in aqueous media. Tetrahedron Lett., 2007, 48, 3299-3303.
Khurana, J.M.; Nand, B.; Saluja, P. DBU: a highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano [4,3-b] pyranes, 2-amino-4Hbenzo [h] chromenes and 2-amino-4H benzo[g]chromenes in aqueous medium. Tetrahed, 2010, 66(30), 5637-5641.
Sheikhhosseini, E. Ghazanfari, D.:Nezamabadi, V.:A new method for synthesis of tetrahydrobenzo[b]pyrans and dihydropyrano[c]chromenes using p-dodecylbenzenesulfonic acid as catalyst in water, Iran. J. Catal., 2013, 3(4), 197-201.
Zonouzi, A.; Mirzazadeh, R.; Safavi, M.; Kabudanian Ardestani, S.; Emami, S.; Foroumadi, A. 2-Amino-4-(nitroalkyl)-4H-chromene-3-carbonitriles as New Cytotoxic Agents. Iran. J. Pharm. Res., 2013, 12(4), 679-685.
[PMID: 24523747]
Ghaffari Khaligh, N. Synthesis and characterization of some novel 4-arylglyoxal-chromene derivatives in the presence of a polymeric catalyst and biological evaluation against Escherichia coli. MonatsheftefürChemie, 2018, 149(1), 33-38.
Zavar, S. A novel three component synthesis of 2-amino-4Hchromenes derivatives using nanoZnO catalyst. Arab. J. Chem., 2017, 10, S67-S70.
Vijaykumar, J.M. Rupali L. M.:Prashant, B.T.:Sunil, U.T.:Bhagavan, R. P.:Mangal P. K.:Rajendra P.P. Chin. Chem. Lett., 2014, 25(3), 455-458.
Ezzatzadeh, E. Hossaini, Z.:Rostamian, R.:Vaseghi, S.:Mousavi, S. F.:Fe3O4magnetic nanoparticles (MNPs) as reusable catalyst for the synthesisof chromene derivatives using multicomponent reaction of4-Hydroxycumarin basis on cheletropic reaction. J. Heterocycl. Chem., 2014, 54, 2906-2911.
Sharma, P. Gupta, M.: Kant, R.: Gupta, V. K.:One-pot synthesis of various 2-amino-4H-chromene derivatives using a highly active supported ionic liquid catalyst. RSC Advances, 2016, 38, 32052.
Safari, J. Heydarian, M.: Zarnegar, Z.:Synthesis of 2-amino-7-hydroxy-4H-chromene derivatives under ultrasound irradiation: A rapid procedure without catalyst. Arab. J. Chem., 2017, 10, S2994.
Magara, R.L. Thorat, P.B.: Patil, B.R.: Pawar, R.P. Organocatalyzed synthesis of 2-Amino-4H-Chromenes: Annantioselective Approach. Curr. Organocatal., 2018, 5, 74-81.
Adeyemo, A.A. Olatunbosun, A. I.: Solomon, B.O.: Metal organic frameworks as adsorbents for dye adsorption: overview,prospects and future challenges. Toxicol. Environ. Chem., 2012, 94(10), 1846-1863.
Hu, L. Deng, G.: Lu, W.: Lu, Y.: Zhang, Y.:Peroxy mono sulfate activation by Mn3O4/metal‐organic framework for degradation of refractory aqueous organic pollutant rhodamine B. Chin. J. Catal., 2017, 38, 1360-1372.
Hashemian, S. Sedrpoushan, A. R.: HosseiniEshbala, F.: Co-Zeolite Imidazolate Frameworks (ZIF-9@Zeolite) as Heterogen Catalyst for Alcohols Oxidation. Catal. Lett., 2017, 147, 196-203.
Hadinejad, E. Hashemian, S.:Yasini,S. A.: Comparison of catalytic effect of Fe-MOF and Fe-ZIF for Fenton degradation of Eriochrome black T, Desal. Water Treat., 2017, 90, 180-188.
Farzaneh, F. Hamidipour,L.:Mn-Metal Organic Framework as Heterogenous Catalyst for Oxidation of Alkanes and Alkenes, J. Sci. Islamic Republic of Iran, 2016, 27(1), 31-37.
Majedi, A. Davar, F.: Abbasi,A. R.: Metal-organic framework materials as nanophotocatalyst. Int. J. Nanodimens., 2016, 7(1), 1-14.
Amiri, S. Hashemian, S.:Mohebat, R.:Zeoliticimidazolate framework supported on silica for removal of bromophenol blue, Desal. Water Treat., 2017, 86, 165-173.
Gross, A.F.; Sherman, E.; Vajo, J.J. Aqueous room temperature synthesis of cobalt and zinc sodalite zeolitic imidizolate frameworks. Dalton Trans., 2012, 41(18), 5458-5460.
[] [PMID: 22406684]
Andrew Lin, K.Y. Chang,H. A.: ZeoliticImidazoleFramework-67(ZIF-67) as a heterogeneous catalyst to activate peroxy mono sulfate for degradation of Rhodamine B in water. J. Taiwan Inst. Chem. Eng., 2015, 53, 40-45.
Liu, X. Jin,H.: Li,Y.:Bux,H.: Hu,Z.: Ban, Y.: Yang,W.: Metal-organic framework ZIF-8 nanocomposite membrane for efficient recovery of furfural via pervaporation and vapor permeation. J. Membr. Sci., 2013, 428, 498-506.
Basu, S. Maes,M.: Cano-Odena, A.: Alaerts, L.: Vos, D.E.D.: Vankelecom,I. F.J.: Solvent resistant nanofiltration (SRNF) membranes based on metal-organic frameworks. J. Membr. Sci., 2009, 344, 190-198.
Iordanova, R. Bachvarova-Nedelcheva, A.: Dimitriev, Y.: Iliev,Tz.: Mechanochemical synthesis and photocatalytic properties of zinc titanates. Bulg. Chem. Commun, 2011, 43(3), 378-382.
Wei, F.H. Chen,D.: Liang,Z.: Zhao,S.-qi: Luo,Y.: Synthesis and characterization of metal-organic frameworks fabricated by microwave-assisted ball milling for adsorptive removal of Congo red from aqueous solutions. RSC Advances, 2017, 7, 46520-46528.
Tian, H. Wang,S.: Zhang, C.: Veder, J.P.: Pan, J., Jaroniec, M., Wang, L.: Liu, J.: Design and synthesis of porous ZnTiO3/TiO2 nanocages with heterojunctions for enhanced photocatalytic H2 production. J. Mater. Chem. A Mater. Energy Sustain., 2017, 23(5), 11615-11622.
Perween, S. Ranjan,A.: Improved visible-light photocatalytic activity in ZnTiO3 nanopowder prepared by sol-electrospinning. Sol. Energy Mater. Sol. Cells, 2017, 163, 148-156.
Liu, S. Qu,Y.: Li, R.: Wang, G.: Li,Y.:Photocatalytic activity of MTiO3 (M = Ca, Ni, and Zn) nanocrystals for water decomposition to hydrogen. J. Mater. Res., 2014, 29(11), 1295-1301.
Stoyanova, A. Hitkova, H.:bachvarova-nedelcheva,A.:Iordanova, R.: Ivanova, N.: Sredkova, M.: Synthesis, photocatalytic and antibacterial properties of nanosized ZnTiO3 powders obtained by different sol-gel methods. Dig. J. Nanomater. Biostruct., 2012, 7(2), 777-784.
Niknam, K.; Jamali, A. Silica-Bonded N-Propylpiperazine Sodium n-Propionate as Recyclable Basic Catalyst for Synthesis of 3,4-Dihydropyrano[c]chromenederivatives and biscoumarins. Dig. J. Nanomater. Biostruct., 2012, 33, 1840-1849.
Jitender, M.K. Kumar, S.: Tetrabutylammonium bromide (TBAB): a neutral and efficient catalyst for the synthesis of biscoumarin and 3,4-dihydropyrano[c]chromene derivatives in water and solvent-free conditions. Tetra.Lett., 2009, 50, 4125-4127.
Wang, Y.Ye. H.: Zuo, G.:Luo, J.:Synthesis of a novel poly (ethylene glycol) grafted N,N-dimethylaminopyridine functionalized dicationic ionic liquid and its application in one-pot synthesis of 3,4-dihydropyrano[3,2-c]chromene derivatives in water. J. Mol. Liq., 2015, 212, 418-422.
Hazeri, N. TaherMaghsoodlou, M.: Mir, F.: Kangani, M.:Saravani, H.:Molashahi, E.: An Efficientone‐potthree‐component Synthesis of tetrahydrobenzo[b]pyranand3,4‐dihydropyrano[c]chromene derivatives using starch solutionas catalyst. Chin. J. Catal., 2014, 35, 391-395.

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