4-Hydroxypyridinium Antimony Tetrachloride-Functionalized Silica Gel Nanoparticles-Catalyzed One-Pot Synthesis of Naphtho-Bis-[1,3]-Oxazin-3-One/Thione

References

• (a) P. Laszlo, Organic Reactions: Simplicity and Logic (New York: Wiley, 1995);
   Google Scholar
  (b) N. Kaur, P. Bhardwaj, M. Devi, Y. Verma, N. Ahlawat, and P. Grewal “Ionic Liquids for the Synthesis of Five-Membered N,N-,N,N,N- and N,N,N,N-Heterocycles,” Current Organic Chemistry 23, no. 11 (2019): 1214–38.
   Web of Science ®Google Scholar
• R. Afshari and A. Shaabani, “Materials Functionalization with Multicomponent Reactions: State of the Art,” ACS Combinatorial Science 20, no. 9 (2018): 499–528.
   PubMed Web of Science ®Google Scholar
• D. Insuasty, J. Castillo, D. Becerra, H. Rojas, and R. Abonia, “Synthesis of Biologically Active Molecules through Multicomponent Reactions,” Molecules 25, no. 3 (2020): 505.
   PubMed Web of Science ®Google Scholar
• M. Patel, R. J. McHugh, B. C. Cordova, R. M. Klabe, S. Erickson-Viitanen, G. L. Trainor, and S. S. Ko, “Synthesis and Evaluation of Benzoxazinones as HIV-1 Reverse Transcriptase Inhibitors. Analogs of Efavirenz (SUSTIVATM),” Bioorganic and Medicinal Chemistry Letters 9, no. 22 (1999): 3221–4.
   PubMed Web of Science ®Google Scholar
• T. Haneishi, T. Okazaki, T. Hata, C. Tamura, M. Nomura, A. Naito, I. Seki, and M. Arai, “Oxazinomycin, a New Carbon-Linked Nugleoside Antibiotic,” The Journal of Antibiotics 24, no. 11 (1971): 797–9.
   PubMed Web of Science ®Google Scholar
• K. Sasaki, Y. Kusakabe, and S. Esumi, “The Structure of Minimycin, A Novel Carbon-Linked Nucleoside Antibiotic Related to β-Pseudouridine,” The Journal of Antibiotics 25, no. 3 (1972): 151–4.
   PubMed Web of Science ®Google Scholar
• Y. Kusakabe, J. Nagatsu, M. Shibuya, O. Kawaguchi, C. Hirose, and S. Shirato, “Minimycin, A New Antibiotic,” The Journal of Antibiotics 25, no. 1 (1972): 44–7.
   PubMed Web of Science ®Google Scholar
• S. M. Kupchan, Y. Komoda, W. A. Court, G. J. Thomas, R. M. Smith, A. Karim, C. J. Gilmore, R. C. Haltiwanger, and R. F. Bryan, “Tumor Inhibitors. LXXIII. Maytansine, a Novel Antileukemic Ansa Macrolide from Maytenus Ovatus,” Journal of the American Chemical Society 94, no. 4 (1972): 1354–6.
   PubMed Web of Science ®Google Scholar
• M. C. Wani, H. L. Taylor, and M. E. Wall, “Plant Antitumour Agents.: XII. Texensine, a New Peptide Alkaloid from Colubrina Texensis,” Chemical Communications 14, no. 47 (1973): 4675–8.
   Google Scholar
• P. Y. Johnson and R. B. Silver, “The Synthesis and Antitumor Properties of a 6‐Alkoxy Tetrahydrooxazine,” Journal of Heterocyclic Chemistry 10, no. 6 (1973): 1029–30.
   Web of Science ®Google Scholar
• S. Remillard, L. Rebhun, G. Howie, and S. Kupchan, “Antimitotic Activity of the Potent Tumor Inhibitor Maytansine,” Science 189, no. 4207 (1975): 1002–5.
   PubMed Web of Science ®Google Scholar
• G. Y. Lesher and A. R. Surrey, “A New Method for the Preparation of 3-Substituted-2-Oxazolidones,” Journal of the American Chemical Society 77, no. 3 (1955): 636–41.
   Web of Science ®Google Scholar
• H. S. Mosher, M. B. Frankel, and M. Gregory, “Heterocyclic Diphenylmethane Derivatives,” Journal of the American Chemical Society 75, no. 21 (1953): 5326–8.
   Web of Science ®Google Scholar
• Y. Wang, X. Li, and K. Ding, “Synthesis of a New Type of Chiral Amino Phosphine Ligands for Asymmetric Catalysis,” Tetrahedron: Asymmetry 13, no. 12 (2002): 1291–7.
   Google Scholar
• (a) D. Balouchzehi and A. Hassanabadi, “Synthesis of 2-Aryl-4-Thioxo-4H-Naphtho [2, 3-e][1,3] Oxazine-5, 10-Dione under Solvent-Free Conditions at Ambient Temperature,” Polycyclic Aromatic Compounds 39, (2019): 1–7;
   Google Scholar
  (b) A. Rashidi, M. H. Mosslemin, and A. Hassanabadi, “Synthesis of 2-Aryl-7-Methyl-4-Selenoxo-4H-Pyrano [3, 4-e][1,3] Oxazin-5-One via a Three-Component Condensation,” Phosphorus, Sulfur, Silicon, and the Related. Elements 196, (2021): 497–500 ;
   Web of Science ®Google Scholar
  (c) A. Khazaeian and A. Hassanabadi, “Synthesis of 2-Aryl-7-Methyl-4-Thioxo-4H-Pyrano [3, 4-e][1,3] Oxazin-5-One by Three-Component Condensation,” Journal of Chemical Research 39, (2015) 492–3.
   Google Scholar
• Z. Benzekri, S. Hamia, R. Benhdidou, H. Serrar, S. Boukhris, A. Hassikou, and A. Souizi, “One-Pot Solvent-Free Synthesis of Naphtho [1,2-e][1,3] Oxazin-3-One/Thione Derivatives Using a Snail Shell as a Green and Efficient Catalyst,” Journal of Materials and Environmental Science 8, (2017): 2986–92.
   Google Scholar
• M. Dabiri, A. Delbari, and A. Bazgir, “A Novel Three-Component, One-Pot Synthesis of 1, 2-Dihydro-1-Arylnaphtho [1,2-e][1,3] Oxazine-3-One Derivatives under Microwave-Assisted and Thermal Solvent-Free Conditions,” Synlett 2007, (2007): 821–3.
   Google Scholar
• M. Dabiri, A. Delbari, and A. Bazgir, “A Simple and Environmenttally Benign Method for the Synthesis of Naphthoxazin-3-One Derivatives,” Heterocycles 71, no. 3 (2007): 543–8.
   Web of Science ®Google Scholar
• G. Sabitha, K. Arundhathi, K. Sudhakar, B. S. Sastry, and J. S. Yadav, “A Novel Three-Component One-Pot Reaction Involving β-Naphthol, Aldehydes, and Urea Promoted by TMSCl/NaI,” Journal of Heterocyclic Chemistry 47, (2010): 272–5.
   Web of Science ®Google Scholar
• A. H. Abbastabar, G. H. Mahdavinia, K. Marjani, and A. Hafezian, “A One-Pot Synthesis of 1, 2-Dihydro-1-Arylnaphtho [1, 2-e][1,3] Oxazine-3-One Derivatives Catalyzed by Perchloric Acid Supported on Silica (HClO4/SiO2) in the Absence of Solvent,” Journal of the Iranian Chemical Society 7, no. 3 (2010): 770–4.
   Web of Science ®Google Scholar
• A. CHaskar, V. Vyavhare, V. Padalkar, K. Phatangare, and H. Deokar, “An Environmentally Benign One-Pot Synthesis of 1, 2-Dihydro-1-Arylnaphtho [1, 2-e][1,3] Oxazine-3-One Derivatives Catalysed by Phosphomolybdic Acid,” Journal of the Serbian Chemical Society 76, no. 1 (2011): 21–6.
   Web of Science ®Google Scholar
• S. S. Kottawar, S. A. Siddiqui, and S. R. Bhusare, “A Novel One-Pot Synthesis of 1, 2-Dihydro-1-Phenyl-Naphtho [1, 2-e][1,3] Oxazin-3-Ones,” Rasayan Journal of Chemistry 3, (2010): 646–8.
   Google Scholar
• R. G. B. Dharma, M. P. Kaushik, and A. K. Halve, “An Efficient Synthesis of Naphtha [1,2-e] Oxazinone and 14-Substituted-14H-Dibenzo [a,j] Xanthene Derivatives Promoted by Zinc Oxide Nanoparticle under Thermal and Solvent-Free Conditions,” Tetrahedron Letters 53, no. 22 (2012): 2741–4.
   Web of Science ®Google Scholar
• A. Kumar, A. Saxena, A. De, R. Shankar, and S. Mozumdar, “Facile Synthesis of Size-Tunable Copper and Copper Oxide Nanoparticles Using Reverse Microemulsions,” RSC Advances 3, no. 15 (2013): 5015–21.
   Web of Science ®Google Scholar
• M. Lei, L. Ma, and L. Hu, “Highly Chemoselective Condensation of β-Naphthol, Aldehyde, and Urea Catalyzed by Thiamine Hydrochloride,” Synthetic Communications 41, no. 22 (2011): 3424–32.
   Web of Science ®Google Scholar
• J. Chenggang, G. Xin, Z. Zonglei, X. Hangxian, and W. Cunde, “Chlorotrimethylsilane-Promoted Synthesis of 1, 2-Dihydro-1-Arylnaphtho [1, 2-e][1,3] Oxazine-3-Ones,” Journal of Chemical Research 34, (2010): 19–21.
   Google Scholar
• J. Safaei-Ghomi, S. Zahedi, and M. A. Ghasemzadeh, “ZnO Nanoparticles: A Highly Effective and Readily Recyclable Catalyst for the One-Pot Synthesis of 1, 8-Dioxo-Decahydroacridine and 1, 8-Dioxooctahydro-Xanthene Derivatives,” Iranian Journal of. Catalysis 57, (2013): 1–7.
   Google Scholar
• F. Nemati and A. Beyzai, “A Facile One-Pot Solvent-Free Synthesis of 1, 2-Dihydro-1-Arylnaphtho [1, 2-e][1,3] Oxazine-3-Ones Catalyzed by Wet Cyanuric Chloride,” Journal of Chemistry 2013, (2012): 1–4.
   Google Scholar
• X. Zhu and Y. R. Lee, “RuCl 2 (PPh 3) 3-Catalyzed Facile One-Pot Synthesis of 1, 2-Dihydro-1-Arylnaphtho [1,2-e][1,3] Oxazine-3-Ones and 1, 2-Dihydro-1-Arylnaphtho [1,2-e][1,3] Oxazine-3-Thiones,” Bulletin of the Korean Chemical Society 33, no. 11 (2012): 3831–4.
   Web of Science ®Google Scholar
• F. Dong, Y. Li-Fang, and Y. Jin-Ming, “Synthesis of 1, 2-Dihydro-1-Arylnaphtho [1, 2-e][1,3] Oxazine-3-One Catalyzed by Pyridinium-Based Ionic Liquid,” Research on Chemical Intermediates 39, no. 6 (2013): 2505–12.
   Web of Science ®Google Scholar
• F. Hatamjafari, “A Facile one- Pot Solvent- Free Synthesis of 1,2- Dihydro- 1- arylnaphtho [1,2-e] [1,3] oxazine- 3- one- Catayzed by Nano- Fe2O3,” International Journal of Bio-Inorganic Hybrid Nanomaterials 3, (2014): 111–5.
   Google Scholar
• A. Kumar, A. Saxena, M. Dewan, A. De, and S. Mozumdar, “Recyclable Nanoparticulate Copper Mediated Synthesis of Naphthoxazinones in PEG-400: A Green Approach,” Tetrahedron Letters 52, no. 38 (2011): 4835–9.
   Web of Science ®Google Scholar
• M. Dabiri, S. C. Azimi, H. R. Khavasi, and A. Bazgir, “A Novel Reaction of 6-Amino-Uracils and Isatins,” Tetrahedron 64, no. 30–31 (2008): 7307–11.
   Web of Science ®Google Scholar
• A. Nizam and M. A. Päsha, “Iodine-Catalyzed, Rapid and Efficient, One-Pot Synthesis of 1, 2-Dihydro-1-Arylnaphtho [1, 2 e][1,3] Oxazine-3-Ones under Solvent-Free Conditions,” Synthetic Communications 40, no. 19 (2010): 2864–8.
   Web of Science ®Google Scholar
• H. R. Khavasi, A. Bazgir, V. Amani, and R. Rahimi, “Synthesis and Crystal Structure of 1, 2-Dihydro-1-(4-Chlorophenyl) Naphtho [1, 2-e][1,3] Oxazin-3-One,”Journal of Chemical Research 2008, no. 8 (2008): 450–1.
   Google Scholar
• A. Abdollahi-Irandegan, and A.Hassanabadi, “Synthesis of 4-Aryl-7-Methyl-3, 4-Dihydropyrano [3,4-e][1,3] Oxazine-2, 5-Dione in Aqueous Media, Journal of Chemical Research 40 (2016): 727–8.
   Google Scholar
• A. Hajra, D. Kundu, and A. Majee, “An Efficient One‐Pot Synthesis of Naphthoxazinones by A Three‐Component Coupling of Naphthol, Aldehydes, and Urea Catalyzed by Zinc Triflate,” Journal of Heterocyclic Chemistry 46, no. 5 (2009): 1019–22.
   Web of Science ®Google Scholar
• J. G. Rudick, S. Shaabani, and A. Dömling, “Isocyanide-Based Multicomponent Reactions,” Frontiers in Chemistry 7, (2020): 918.
   PubMed Web of Science ®Google Scholar
• Y. L. Nene and P. N. Thapliyal, Fungicides in Plant Disease Control (New Delhi, India: IBH, 1982).
   Google Scholar