154
Views
4
CrossRef citations to date
0
Altmetric
Articles

Facile route for the synthesis and cytotoxic effect of 2-amino-4H-benzo[b]pyran derivatives in aqueous media using copper oxide nanoparticles decorated on cellulose nanocrystals as heterogeneous catalyst

, , &
Pages 313-321 | Received 01 Sep 2018, Accepted 24 Aug 2019, Published online: 09 Sep 2019

References

  • Mobinikhaledi, A.; Fard, M. A. B. Tetrabutylammonium Bromide in Water as a Green Media for the Synthesis of Pyrano[2,3-d]pyrimidinone and Tetrahydrobenzo[b]pyran Derivatives. Acta Chim. Slov. 2010, 57, 931–935.
  • Armetso, D.; Horspool, W. M.; Martin, N.; Ramos, A.; Seaone, C. Synthesis of Cyclobutenes by the Novel Photochemical Ring Contraction Of 4-Substituted 2-Amino-3,5-Dicyano-6-Phenyl-4h-Pyrans. J. Org. Chem. 1989, 54, 3069–3072. DOI: 10.1021/jo00274a021.
  • Balalaie, S.; Bararjanian, M.; Amani, A. M.; Movassagh, B. (S)-Proline as a Neutral and Efficient Catalyst for the One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives in Aqueous Media. Synlett 2006, 2, 0263–0266. DOI: 10.1055/s-2006-926227.
  • Kumar, D.; Reddy, V. B.; Sharad, S.; Dube, U.; Kapur, S. A Facile One-Pot Green Synthesis and Antibacterial Activity of 2-Amino-4H-Pyrans and 2-Amino-5-Oxo-5,6,7,8-Tetrahydro-4H-Chromenes. Eur. J. Med. Chem. 2009, 44, 3805–3809. DOI: 10.1016/j.ejmech.2009.04.017.
  • Yu, L. Q.; Liu, F.; You, Q. D. One-Pot Synthesis of Tetrahydrobenzo[ b ]Pyran Derivatives Catalyzed by Amines in Aqueous Media. Org. Prep. Proced. Int. 2009, 41, 77–82. DOI: 10.1080/00304940802711275.
  • Sun, W. O.; Zhang, P.; Fan, J.; Chen, S. H.; Zhang, Z. H. Lithium Bromide as a Mild, Efficient, and Recyclable Catalyst for the One-Pot Synthesis of Tetrahydro-4 H -Chromene Derivatives in Aqueous Media. Synth. Commun. 2010, 40, 587–594. DOI: 10.1080/00397910903007079.
  • Banerjee, S.; Horn, A.; Khatri, A.; Sereda, G. A Green One-Pot Multicomponent Synthesis of 4H-Pyrans and Polysubstituted Aniline Derivatives of Biological, Pharmacological, and Optical Applications Using Silica Nanoparticles as Reusable Catalyst. Tetrahedron Lett. 2011, 52, 1878–1881. DOI: 10.1016/j.tetlet.2011.02.031.
  • Davoodnia, A.; Allameh, S.; Fazli, S.; Tavakoli-Hoseini, N. One-pot Synthesis of 2-Amino-3-Cyano-4-Arylsubstituted Tetrahydrobenzo[b]pyrans Catalysed by Silica Gel-Supported Polyphosphoric Acid (PPA-SiO2) as an Efficient and Reusable Catalyst. Chem. Pap. 2011, 65, 714–720.
  • Khurana, J. M.; Chaudhary, A. Efficient and Green Synthesis of 4 H -Pyrans and 4 H -Pyrano[2,3- c ] Pyrazoles Catalyzed by Task-Specific Ionic Liquid [Bmim]OH under Solvent-Free Conditions. Green Chem. Lett. Rev 2012, 5, 633–638. DOI: 10.1080/17518253.2012.691183.
  • Arturo, S.; Fernando, H.; Paulo, C. C.; Yolanda, A.; Joaquin, T.; Francisco, D.; Vazquez, M. A. Infrared Irradiation-Assisted Multicomponent Synthesis of 2-Amino-3-Cyano-4H-Pyran Derivatives. J. Mex. Chem. Soc. 2012, 56, 121–127.
  • Khoobi, M.; Ma’mani, L.; Rezazadeh, F.; Zareie, Z.; Foroumadi, A.; Ramazani, A.; Shafiee, A. One-Pot Synthesis of 4H-Benzo[b]Pyrans and Dihydropyrano[c]Chromenes Using Inorganic–Organic Hybrid Magnetic Nanocatalyst in Water. J. Mol. Catal. A: Chem. 2012, 359, 74–80. DOI: 10.1016/j.molcata.2012.03.023.
  • Guo, R. Y.; An, Z. M.; Mo, L. P.; Wang, R. Z.; Liu, H. X.; Wang, S. X.; Zhang, Z. H. Meglumine: A Novel and Efficient Catalyst for One-Pot, Three-Component Combinatorial Synthesis of Functionalized 2-Amino-4 H -Pyrans. ACS Comb. Sci. 2013, 15, 557–563. DOI: 10.1021/co400107j.
  • Essamlali, Y.; Amadine, O.; Maati, H.; Abdelouahdi, K.; Fihri, A.; Zahouily, M.; Varma, R. S.; Solhy, A. Highly Efficient One-Pot Three-Component Synthesis of Naphthopyran Derivatives in Water Catalyzed by Phosphates. ACS Sustainable Chem. Eng. 2013, 1, 1154–1159. DOI: 10.1021/sc400072s.
  • Azath, I. A.; Puthiaraj, P.; Pitchumani, K. One-Pot Multicomponent Solvent-Free Synthesis of 2-Amino-4 H -Benzo[ b ]pyrans Catalyzed by per-6-Amino-β-Cyclodextrin. ACS Sustainable Chem. Eng. 2013, 1, 174–179. DOI: 10.1021/sc3000866.
  • Brahmachari, G.; Banerjee, B. Facile and One-Pot Access to Diverse and Densely Functionalized 2-Amino-3-Cyano-4 H -Pyrans and Pyran-Annulated Heterocyclic Scaffolds via an Eco-Friendly Multicomponent Reaction at Room Temperature Using Urea as a Novel Organo-Catalyst. ACS Sustainable Chem. Eng. 2014, 2, 411–422. DOI: 10.1021/sc400312n.
  • Kiyani, H.; Ghorbani, F. J. Potassium Phthalimide Promoted Green Multicomponent Tandem Synthesis of 2-Amino-4H-Chromenes and 6-Amino-4H-Pyran-3-Carboxylates. Saudi Chem. Soc. 2014, 18, 689–701. DOI: 10.1016/j.jscs.2014.02.004.
  • Rajput, J. K.; Kaur, G. Synthesis and Applications of CoFe 2 O 4 Nanoparticles for Multicomponent Reactions. Catal. Sci. Technol. 2014, 4, 142–151. DOI: 10.1039/C3CY00594A.
  • Jain, S.; Paliwal, P. K.; Babu, G. N.; Bhatewara, A. DABCO Promoted One-Pot Synthesis of Dihydropyrano(c)Chromene and Pyrano[2,3-d]pyrimidine Derivatives and Their Biological Activities. J. Saudi Chem. Soc. 2014, 18, 535–540. DOI: 10.1016/j.jscs.2011.10.023.
  • Manjulla, G.; Monika, G.; Rajnikant, R.; Vivek, K. G. Salicyldimine-Based Schiff's Complex of Copper(II) as an Efficient Catalyst for the Synthesis of Nitrogen and Oxygen Heterocycles. New J. Chem. 2015, 39, 3578–3587. DOI: 10.1039/C4NJ02391A.
  • Rajput, J. K.; Arora, P.; Kaur, G.; Kaur, M. CuFe2O4 Magnetic Heterogeneous Nanocatalyst: Low Power Sonochemical-Coprecipitation Preparation and Applications in Synthesis of 4H-Chromene-3-Carbonitrile Scaffolds. Ultrason. Sonochem. 2015, 26, 229–240. DOI: 10.1016/j.ultsonch.2015.01.008.
  • Sadeh, F. N.; Maghsoodlou, M. T.; Hazeri, N.; Kangani, M. A Facile and Efficient Synthesis of Tetrahydrobenzo[b]Pyrans Using Lactose as a Green Catalyst. Res. Chem. Intermed. 2015, 41, 5907–5914. DOI: 10.1007/s11164-014-1710-x.
  • Esmaeilpour, M.; Javidi, J.; Dehghani, F.; Dodeji, F. N. A Green One-Pot Three-Component Synthesis of Tetrahydrobenzo[b]Pyran and 3,4-Dihydropyrano[c]chromene Derivatives Using a Fe 3 O 4 @SiO 2 –Imid–PMA n Magnetic Nanocatalyst under Ultrasonic Irradiation or Reflux Conditions. RSC Adv. 2015, 5, 26625–26633. DOI: 10.1039/C5RA01021G.
  • Albadi, J.; Mansournezhad, A. Aqua-Mediated Multicomponent Synthesis of Various 4H-Pyran Derivatives Catalyzed by Poly(4-Vinylpyridine)-Supported Copper Iodide Nanoparticle Catalyst. Res. Chem. Intermed. 2016, 42, 5739–5752. DOI: 10.1007/s11164-015-2400-z.
  • Zhou, Z.; Zhang, Y.; Hu, X. Efficient One-Pot Synthesis of Tetrahydrobenzo[ b ]pyrans by Ethylenediamine Diacetate-Catalyzed Multicomponent Reaction under Solvent-Free Conditions. Polycycl. Aromat. Compd. 2017, 37, 39–45. DOI: 10.1080/10406638.2015.1088042.
  • Dekamin, M. G.; Peyman, S. Z.; Karimi, Z.; Javanshir, S.; Naimi-Jamal, M.,R.; Barikani, M. Sodium Alginate: An Efficient Biopolymeric Catalyst for Green Synthesis of 2-Amino-4H-Pyran Derivatives. Int. J. Biol. Macromol. 2016, 87, 172–179. DOI: 10.1016/j.ijbiomac.2016.01.080.
  • Hamzeh, K.; Mozhgan, S. J. Facile and Efficient Access to Tetrahydrobenzo[b]pyrans Catalyzed by N,N-Dimethylbenzylamine. Heterocycles 2016, 92, 75–85.
  • Naeimi, H.; Zarabi, M. F. Gold Nanoparticles Supported on Thiol-Functionalized Reduced Graphene Oxide as Effective Recyclable Catalyst for Synthesis of Tetrahydro-4H-Chromenes in Aqueous Media. Appl. Organometal. Chem. 2018, 32, e4225. DOI: 10.1002/aoc.4225.
  • Khandan-Barani, K.; Kangani, M.; Mirbaluchzehi, M.; Siroos, Z. Synthesis of Tetrahydrobenzo[b]Pyran and 3,4-Dihydropyrimidinone Derivatives Using Glutamic Acid as an Efficient Catalyst. Inorg. Nano-Met. Chem. 2017, 47, 751–755. DOI: 10.1080/15533174.2016.1212233.
  • Kiyani, H.; Ghorbani, F. Efficient Tandem Synthesis of a Variety of Pyran-Annulated Heterocycles, 3,4-Disubstituted Isoxazol-5(4H)-Ones, and α,β-Unsaturated Nitriles Catalyzed by Potassium Hydrogen Phthalate in Water. Res. Chem. Intermed. 2015, 41, 7847–7882.
  • Pourian, E.; Javanshir, S.; Dolatkhah, Z.; Molaei, S.; Maleki, A. Ultrasonic-Assisted Preparation, Characterization, and Use of Novel Biocompatible Core/Shell Fe 3 O 4 @GA@Isinglass in the Synthesis of 1,4-Dihydropyridine and 4 H -Pyran Derivatives. ACS Omega 2018, 3, 5012–5020. DOI: 10.1021/acsomega.8b00379.
  • Ahmed, K.; Ali, M. A.; Moustafa, O. A.; El-Wassimy, M. T. One‐Pot Multicomponent Synthesis of Novel 2‐Tosyloxyphenylpyrans under Green and Conventional Condition with Anti‐inflammatory Activity. J. Heterocyclic Chem. 2017, 54, 1442–1449. DOI: 10.1002/jhet.2730.
  • Sakineh, A.; Majid, M. Synthesis and Characterization of Pyridine-4-Carboxylic Acid-Functionalized Fe3O4 Nanoparticles as a Magnetic Catalyst for the Synthesis of Tetrahydrobenzo[B]pyran Derivatives Under Solvent-Free Conditions. Inorg. Nano-Met. Chem. 2017, 47, 1004–1011.
  • Kiyani, H. Recent Advances in Three-Component Cyclocondensation of Dimedone with Aldehydes and Malononitrile for Construction of Tetrahydrobenzo[b]pyrans Using Organocatalysts. Current Org. Synth. 2018, 15, 1043–1072. DOI: 10.2174/1570179415666181031124459.
  • Dong, C.; Zhang, H.; Pang, Z.; Liu, Y.; Zhang, F. Sulfonated Modification of Cotton Linter and Its Application as Adsorbent for High-Efficiency Removal of Lead(II) in Effluent. Bioresour. Technol. 2013, 146, 512–518. DOI: 10.1016/j.biortech.2013.07.108.
  • Madhu, K.; Moores, A. Review: Nanocelluloses as Versatile Supports for Metal Nanoparticles and Their Applications in Catalysis. Green Chem. 2016, 18, 622–637. DOI: 10.1039/C5GC02500A.
  • Geyer, U.; Heinze, T.; Stein, A.; Klemm, D.; Marsch, S.; Schumann, D.; Schmauder, H. P. Formation, Derivatization and Applications of Bacterial Cellulose. Int. J. Biol. Macromol. 1994, 16, 343–347.
  • Ma, M.; Qing, S.; Li, S.; Zhu, J.; Fu, L.; Sun, R. Microwave Synthesis of Cellulose/CuO Nanocomposites in Ionic Liquid and Its Thermal Transformation to CuO. Carbohydr. Polym. 2013, 91, 162–168. DOI: 10.1016/j.carbpol.2012.08.025.
  • Zhou, Z.; Lu, C.; Wu, X.; Zhang, X. Cellulose Nanocrystals as a Novel Support for CuO Nanoparticles Catalysts: facile Synthesis and Their Application to 4-Nitrophenol Reduction. RSC Adv. 2013, 3, 26066–26073. DOI: 10.1039/c3ra43006e.
  • Clarina, T.; Priya Dharsini, G. R.; Rama, V. Synthesis, Characterization and In Vitro Antibacterial Effect of 4H-Benzo[g]chromene Derivatives using Nano-NiO. Chem. Sci. Trans. 2017, 6, 523–534.
  • Priya Dharsini, G. R.; Clarina, T.; Rama, V. Synthesis, Characterization, Chemical Nuclease Activity and Antimicrobial Evaluation of Tridentate (NOS Donor) Schiff Base Ligand: 2-(4-(Thiophen-2-yl)but-3-en-2-ylideneamino)phenol and their Metal-Organic Hybrids. Chem. Sci. Trans. 2017, 6, 637–645.
  • Shukla, S. K.; Nidhi, S.; Pooja, N.; Charu, A.; Silvi, M.; Rizwana, A.,B.; Dubey, G. C.; Ashutosh, T. Preparation And Characterization Of Cellulose Derived From Rice Husk For Drug Delivery. Adv. Mat. Lett. 2013, 4, 714–719.
  • Radhakrishnan, A. A.; Beena, B. B. Structural and Optical Absorption Analysis of CuO Nanoparticles. Ind. J. Adv. Chem. Sci. 2014, 2, 158–161.
  • Zain, N. F. M.; Yusop, S. M.; Ahamed, I. Preparation and characterization of cellulose and nanocellulose from Pomelo (Citrus grandis) Albedo. J. Nutr. Food Sci. 2014, 5, 334– 337.
  • Mosmann, T. Rapid Colorimetric Assay for Cellular Growth and Survival: application to Proliferation and Cytotoxicity Assays. J. Immunol. Methods. 1983, 65, 55–63. DOI: 10.1016/0022-1759(83)90303-4.
  • Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A.; et al. Feasibility of a High-Flux Anticancer Drug Screen Using a Diverse Panel of Cultured Human Tumor Cell Lines. J. Natl. Cancer Inst. 1991, 83, 757–766. DOI: 10.1093/jnci/83.11.757.
  • Wang, X.; Yang, J.; Shi, L.; Gao, M. Surfactant-Free Synthesis of CuO with Controllable Morphologies and Enhanced Photocatalytic Property. Nanoscale Res. Lett. 2016, 11, 125–131.
  • Trung, D. B.; Hanh, N. N. Nanocellulose: extraction from non-wood crop residues and application in nanocomposite.Vietnam J. Chem. 2013, 51, 403–407.
  • Trung, D. B.; Hanh, N. N. Comparison of nanocellulose extraction from hardwood and softwood agricultural residues. Vietnam J. Sci. Tech. 2013, 51, 184–189.
  • Kotal, A.; Paira, T. K.; Banerjee, S.; Mandal, T. K. Ultrasound-Induced in Situ Formation of Coordination Organogels from Isobutyric Acids and Zinc Oxide Nanoparticles. Langmuir 2010, 26, 6576–6582. DOI: 10.1021/la903923q.
  • Mushtag, A. D.; Sang, H. N.; Youn, S. K.; Won, B. K. Synthesis, Characterization, and Electrochemical Properties of Self-Assembled Leaf-Like CuO Nanostructures J. Solid State Electrochem. 2010, 14, 1719–1726.
  • Hu, H.; Qiu, F.; Ying, A.; Yang, J.; Meng, H. An Environmentally Benign Protocol for Aqueous Synthesis of Tetrahydrobenzo[b]Pyrans Catalyzed by Cost-Effective Ionic Liquid. Int. J. Mol. Sci. 2014, 15, 6897–6909. DOI: 10.3390/ijms15046897.
  • Beheshtiha, S. Y.; Oskooie, H. A.; Pourebrahimi, F. S.; Zadsirjan, V. Hexamethylenetetramine as an Efficient Catalyst for One-Pot, Three Component Synthesis of 2-Amino-4H-Pyran Derivatives. Chem. Sci. Trans. 2015, 4, 689–693.
  • Baghbanian, S. M.; Rezaei, N.; Tashakkorian, H. Nanozeolite Clinoptilolite as a Highly Efficient Heterogeneous Catalyst for the Synthesis of Various 2-Amino-4H-Chromene Derivatives in Aqueous Media. Green Chem. 2013, 15, 3446–3458. DOI: 10.1039/c3gc41302k.
  • Hekmatshoar, R.; Majedi, S.; Bakhtiari, K. Sodium Selenate Catalyzed Simple and Efficient Synthesis of Tetrahydro Benzo[b]Pyran Derivatives. Catal. Commun. 2008, 9, 307–310. DOI: 10.1016/j.catcom.2007.06.016.
  • Katkar, S. S.; Lande, M. K.; Arbad, B. R.; Gaikwad, S. T. A Recyclable and Highly Effective ZnO-Beta Zeolite as a Catalyst for One-Pot Three-Component Synthesis of Tetrahydrobenzo[b]Pyrans. Chin. J. Chem. 2011, 29, 199–202. DOI: 10.1002/cjoc.201190052.
  • Chen, L.; Lin, J.; Chen, B.; Zhao, L. Sodium Ethylene Diamine Tetraacetate Catalyzed Synthesis of Chromene Derivatives via Multi-Component Reactions at Low Catalyst Loading. Res. Chem. Intermed. 2017, 43, 6691–6700. DOI: 10.1007/s11164-017-3015-3.
  • Dekamin, M. G.; Eslami, M. Highly Efficient Organocatalytic Synthesis of Diverse and Densely Functionalized 2-Amino-3-Cyano-4H-Pyrans under Mechanochemical Ball Milling. Green Chem. 2014, 16, 4914–4921. DOI: 10.1039/C4GC00411F.
  • Chen, L.; Li, Y. Q.; Huang, X. J.; Zheng, W. N, N -Dimethylamino-Functionalized Basic Ionic Liquid Catalyzed One-Pot Multicomponent Reaction for the Synthesis of 4 H -Benzo[ b ]Pyran Derivatives under Solvent-Free Condition. Heteroatom Chem. 2009, 20, 91–94. DOI: 10.1002/hc.20516.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.