Synthesis of Benzodiazepines Promoted by CeO₂/CuO@Nitrogen Graphene Quantum Dots@NH₂ Nanocomposite

References

• L. Z. Wang, X. Q. Li, and Y. S. An, “1,5-Benzodiazepine derivatives as potential antimicrobial agents: design, synthesis, biological evaluation, and structure-activity relationships,” Organic & Biomolecular Chemistry 13, no. 19 (2015): 5497–509.
   PubMed Web of Science ®Google Scholar
• Y. Chen, V. Le, X. Xu, X. Shao, J. Liu, and Z. Li, “Discovery of novel 1,5-benzodiazepine-2,4-dione derivatives as potential anticancer agents,” Bioorganic & Medicinal Chemistry Letters 24, no. 16 (2014): 3948–51.
   PubMed Web of Science ®Google Scholar
• B. E. Leonard, “Therapeutic applications of benzodiazepine receptor ligands in anxiety,” Human Psychopharmacology: Clinical and Experimental 14, no. 2 (1999): 125–35.
   Web of Science ®Google Scholar
• Jiří Schimer, Petr Cígler, Jan Veselý, Klára Grantz Šašková, Martin Lepšík, Jiří Brynda, Pavlína Rezáčová, Milan Kožíšek, Ivana Císařová, Heike Oberwinkler, et al. “Structure-aided design of novel inhibitors of HIV protease based on a benzodiazepine scaffold,” Journal of Medicinal Chemistry 55, no. 22 (2012): 10130–5.,
   PubMed Web of Science ®Google Scholar
• P. Chen, Q. Zhang, Y. B. Ma, Z. Y. Jiang, X. M. Zhang, F. X. Zhang, and J. J. Chen, “Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloro-quinolin-2-one and 5-aryl-7-chloro-1,4-benzodiazepine derivatives,” Bioorganic & Medicinal Chemistry Letters 18, no. 13 (2008): 3787–9.
   PubMed Web of Science ®Google Scholar
• G. Maiti, U. Kayal, R. Karmakar, and R. N. Bhattacharya, “Terminal alkynes as keto-methyl equivalent toward one pot synthesis of 1, 5-benzodiazepine derivatives under catalysis of Hg (OTf)2,” Tetrahedron Letters 53, no. 12 (2012): 1460–3.
   Web of Science ®Google Scholar
• H. Thakuria, A. Pramanik, B. M. Borah, and G. Das, “A One-pot synthesis and self-assembled superstructure of organic salts of a 1, 5-benzodiazepine derivative,” Tetrahedron Letters 47, no. 18 (2006): 3135–8.
   Web of Science ®Google Scholar
• M. Curini, F. Epifano, M. C. Marcotullio, and O. Rosati, “Ytterbium triflate promoted synthesis of 1, 5-benzodiazepine derivatives,” Tetrahedron Letters 42, no. 18 (2001): 3193–5.
   Web of Science ®Google Scholar
• R. Varala, R. Enugala, S. Nuvula, and S. R. Adapa, “Ceric ammonium nitrate (CAN) promoted efficient synthesis of 1, 5-benzodiazepine derivatives,” Synlett 2006, no. 07 (2006): 1009–14.
   Google Scholar
• S. K. De, and R. A. Gibbs, “Scandium (III) triflate as an efficient and reusable catalyst for synthesis of 1, 5-benzodiazepine derivatives,” Tetrahedron Letters 46, no. 11 (2005): 1811–3.
   Web of Science ®Google Scholar
• T. D. Le, K. D. Nguyen, V. T. Nguyen, T. Truong, and N. T. S. Phan, “1,5-Benzodiazepine synthesis via cyclocondensation of 1,2-diamines with ketones using iron-based metal–organic framework MOF-235 as an efficient heterogeneous catalyst,” Journal of Catalysis 333, (2016): 94–101.
   Web of Science ®Google Scholar
• J. Wang, L. Wang, S. Guo, S. Zha, and J. Zhu, “Synthesis of 2,3-benzodiazepines via Rh(III)-catalyzed C-H functionalization of N-Boc hydrazones with diazoketoesters,” Organic Letters 19, no. 13 (2017): 3640–3.
   PubMed Web of Science ®Google Scholar
• M. M. Korbekandi, M. Nasr-Esfahani, I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad, and V. Mirkhani, “Preparation and application of a new supported nicotine-based organocatalyst for synthesis of various 1,5-benzodiazepines,”Catalysis Letters 149, no. 4 (2019): 1057–66.
   Web of Science ®Google Scholar
• M. T. Jafari-Chermahini, H. Tavakol, and W. Salvenmoser, “Sulfur–doped graphene as an efficient metal–free carbocatalyst for the synthesis of 1,5–benzodiazepines derivatives,” Chemistryselect 5, no. 3 (2020): 968–78.
   Web of Science ®Google Scholar
• J. Safaei-Ghomi, and H. Shahbazi-Alavi, “Synthesis of 2-oxo-pyridines catalyzed by biosynthesized CuO nanoparticles,” Polycyclic Aromatic Compounds 51, (2019): 1–5.
   Google Scholar
• M. Roushani, A. Valipour, and M. Bahrami, “The potentiality of graphene quantum dots functionalized by nitrogen and thiol-doped (GQDs-N-S) to stabilize the antibodies in designing of human chorionic gonadotropin immunosensor,” Nanochemical Research 4, (2019): 20–6.
   Google Scholar
• Behiye Şenel, Neslihan Demir, Gülay Büyükköroğlu, and Mustafa Yıldız, “Graphene quantum dots: synthesis, characterization, cell viability, genotoxicity for biomedical applications,” Saudi Pharmaceutical Journal 27, no. 6 (2019): 846–58.
   PubMed Web of Science ®Google Scholar
• M. J. Molaei, “Carbon quantum dots and their biomedical and therapeutic applications: a review,” RSC Advances 9, no. 12 (2019): 6460–81.
   PubMed Web of Science ®Google Scholar
• T. F. Yeh, C. Y. Teng, S. J. Chen, and H. Teng, “Nitrogen-doped graphene oxide quantum dots as photocatalysts for overall water-splitting under visible light illumination,” Advanced Materials (Deerfield Beach, Fla.) 26, no. 20 (2014): 3297–303.
   PubMed Web of Science ®Google Scholar
• F. Xi, J. Zhao, C. Shen, J. He, J. Chen, Y. Yan, K. Li, J. Liu, and P. Chen, “Amphiphilic graphene quantum dots as a new class of surfactants,” Carbon 153, (2019): 127–35.
   Web of Science ®Google Scholar
• Y. Wang, Y. Shao, D. W. Matson, J. Li, and Y. Lin, “Nitrogen-doped graphene and its application in electrochemical biosensing,”ACS Nano 4, no. 4 (2010): 1790–8.
   PubMed Web of Science ®Google Scholar
• Q. Li, S. Zhang, L. Dai, and L. S. Li, “Nitrogen-doped colloidal graphene quantum dots and their size-dependent electrocatalytic activity for the oxygen reduction reaction,” Journal of the American Chemical Society 134, no. 46 (2012): 18932–5. − 
   PubMed Web of Science ®Google Scholar
• A. L. M. Reddy, A. Srivastava, S. R. Gowda, H. Gullapalli, M. Dubey, and P. M. Ajayan, “Synthesis of nitrogen-doped graphene films for lithium battery application,” ACS Nano 4, no. 11 (2010): 6337–42.
   PubMed Web of Science ®Google Scholar
• M. T. Hasan, R. Gonzalez-Rodriguez, C. Ryan, K. Pota, K. Green, J. L. Coffer, and A. V. Naumov, “Nitrogen-doped graphene quantum dots: optical properties modification and photovoltaic applications,” Nano Research 12, no. 5 (2019): 1041–7.
   Web of Science ®Google Scholar
• Filipp Temerov, Andrey Belyaev, Bright Ankudze, and Tuula T. Pakkanen, “Preparation and photoluminescence properties of graphene quantum dots by decomposition of graphene-encapsulated metal nanoparticles derived from Kraft Lignin and transition metal salts,” Journal of Luminescense. 206, (2019): 403–11.
   Web of Science ®Google Scholar
• S. Zhu, Y. Song, X. Zhao, J. Shao, J. Zhang, and B. Yang, “Investigating the surface state of graphene quantum dots,” Nano Research 8, no. 2 (2015): 355–81.
   Web of Science ®Google Scholar
• D. Qu, M. Zheng, J. Li, Z. Xie, and Z. Sun, “Tailoring color emissions from N-doped graphene quantum dots for bioimaging applications,” Light: Science & Applications 4, no. 12 (2015): e364–371.
   Google Scholar
• S. Sajjadi, A. Khataee, R. D. C. Soltani, and A. Hasanzadeh, “N, S co-doped graphene quantum dot–decorated Fe3O4 nanostructures: preparation, characterization and catalytic activity,” Journal of Physical Chemistry Solids. 127, (2019): 140–50.
   Web of Science ®Google Scholar
• Y. Du, and S. Guo, “Chemically doped fluorescent carbon and graphene quantum dots for bioimaging, sensor, catalytic and photoelectronic applications,”Nanoscale 8, no. 5 (2016): 2532–43.
   PubMed Web of Science ®Google Scholar
• Y. Yan, J. Gong, J. Chen, Z. Zeng, W. Huang, K. Pu, J. Liu, and P. Chen, “Recent advances on graphene quantum dots: from chemistry and physics to applications,” Advanced Materials 31, no. 21 (2019): 1808283–305.
   Web of Science ®Google Scholar
• M. Li, T. Chen, J. J. Gooding, and J. Liu, “Review of carbon and graphene quantum dots for sensing,” ACS Sensors 4, no. 7 (2019): 1732–48.
   PubMed Web of Science ®Google Scholar
• Z. Wang, H. Zeng, and L. Sun, “Graphene quantum dots: versatile photoluminescence for energy, biomedical, and environmental applications,” Journal of Materials Chemistry C 3, no. 6 (2015): 1157–65.
   PubMed Web of Science ®Google Scholar
• D. Qu, M. Zheng, P. Du, Y. Zhou, L. Zhang, D. Li, H. Tan, Z. Zhao, Z. Xie, and Z. Sun, “Highly luminescent S, N co-doped graphene quantum dots with broad visible absorption bands for visible light photocatalysts,” Nanoscale 5, no. 24 (2013): 12272–7.
   PubMed Web of Science ®Google Scholar
• A. Maleki, and M. Kamalzare, “An efficient synthesis of benzodiazepine derivatives via a one-pot, three-component reaction accelerated by a chitosan-supported superparamagnetic iron oxide nanocomposite,” Tetrahedron Letters 55, no. 50 (2014): 6931–4.
   Web of Science ®Google Scholar
• N. N. Kolos, E. N. Yurchenko, V. D. Orlov, S. V. Shishkina, and O. V. Shishkin, “Investigation of the products of interaction of cyclic diketones with nitrogen-containing 1,4-binucleophiles,” Chemistry of Heterocyclic Compounds 40, no. 12 (2004): 1550–9.
   Google Scholar
• A. Shaabani, A. H. Rezayan, S. Keshipour, A. Sarvary, and S. W. Ng, “A novel one-pot three-(in situ five-)component condensation reaction: an unexpected approach for the synthesis of tetrahydro-2,4-dioxo-1H-benzo[b][1,5]diazepine-3-yl-2-methylpropanamide derivatives,” Organic Letters 11, no. 15 (2009): 3342–5.
   PubMed Web of Science ®Google Scholar
• M. A. Ghasemzadeh, and N. Ghasemi-Seresht, “Facile and efficient synthesis of benzo[b][1,5]diazepines by three-component coupling of aromatic diamines, meldrum’s acid, and isocyanides catalyzed by Fe3O4 nanoparticles,” Research on Chemical Intermediates 41, no. 11 (2015): 8625–36.
   Web of Science ®Google Scholar
• N. N. Tonkikh, A. Strakovs, K. V. Rizhanova, and M. V. Petrova, “11-aryl-3,3-Dimethyl-7- and 7,8-substituted 1,2,3,4,10,11-hexahydro-5h-dibenzo[b,e]-1,4-diazepin-1-ones,” Chemistry of Heterocyclic Compounds 40, no. 7 (2004): 949–55.
   Google Scholar
• S. M. Vahdat, and S. Baghery, “An efficient one-pot synthesis of 1,8-dioxo-decahydroacridines by indium(Iii)chloride under ambient temperature in ethanol,” Heterocyclc Letters 2, (2012): 43–51.
   Google Scholar
• A. Maleki, and R. Paydar, “Graphene oxide–chitosan bionanocomposite: a highly efficient nanocatalyst for the one-pot three-component synthesis of trisubstituted imidazoles under solvent-free conditions,” RSC Advances 5, no. 42 (2015): 33177–84.
   Web of Science ®Google Scholar
• J. Safaei-Ghomi, H. Shahbazi-Alavi, and P. Babaei, “One-pot multicomponent synthesis of furo[3,2-c]coumarins promoted by amino-functionalized Fe3O4@SiO2 nanoparticles,” Zeitschrift Für Naturforschung B 71, no. 8 (2016): 849–56.
   Google Scholar