β‐Cyclodextrin: An Efficient Supramolecular Catalyst for the Synthesis of Pyranoquinolines Derivatives under Ultrasonic Irradiation in Water

Reference

• C. K. Jadhav, A. S. Nipate, A. V. Chate, P. M.  Kamble, G. A. Kadam, V. S. Dofe, V. M. Khedkar, and C. H. Gill, “Room Temperature Ionic Liquid Promoted Improved and Rapid Synthesis of Highly Functionalized Imidazole and Evaluation of Their Inhibitory Activity against Human Cancer Cells,” Journal of the Chinese Chemical Society (2021).
   PubMed Web of Science ®Google Scholar
• R. C. Cioc, E. Ruijter, and R. V. A. Orru, “Multicomponent Reactions: advanced Tools for Sustainable Organic Synthesis,” Green Chemistry. 16, no. 6 (2014): 2958–75.
   Web of Science ®Google Scholar
• M. Mamaghani, and R. Hossein Nia, “A Review on the Recent Multicomponent Synthesis of Pyranopyrazoles,” Polycyclic Aromatic Compounds, (2019): 1–69.
   Web of Science ®Google Scholar
• A. Dömling, W. Wang, and K. Wang, “Chemistry and Biology of Multicomponent Reactions,” Chemical Reviews 112, no. 6 (2012): 3083–135.
   PubMed Web of Science ®Google Scholar
• R. Mishra, A. Jana, A. K. Panday, and L. H. Choudhury, “Synthesis of Spirooxindoles Fused with Pyrazolo-Tetrahydropyridinone and Coumarin-Dihydropyridine-Pyrazole Tetracycles by Reaction Medium Dependent Isatin-Based Multicomponent Reactions,” New Journal of Chemistry 43, no. 7 (2019): 2920–32.
   Web of Science ®Google Scholar
• D. S. Aher, K. R. Khillare, L. D. Chavan, and S. G. Shankarwar, “Quaternary Vanado‐Molybdotungstophosphoric Acid [H 5 PW 6 Mo 4 V 2 O 40] over Natural Montmorillonite as a Heterogeneous Catalyst for the Synthesis 4 H ‐Pyran and Polyhydroquinoline Derivatives,” ChemistrySelect 5, no. 25 (2020): 7320–31.
   Web of Science ®Google Scholar
• C. K. Jadhav, A. S. Nipate, A. V. Chate, V. D. Songire, A. P. Patil, and C. H. Gill, “Efficient Rapid Access to Biginelli for the Multicomponent Synthesis of 1,2,3,4-Tetrahydropyrimidines in Room-Temperature Diisopropyl Ethyl Ammonium Acetate,” ACS Omega 4, no. 27 (2019): 22313–24.
   PubMed Web of Science ®Google Scholar
• J. Safari, and N. H. Nasab, “Ultrasonic Activated Efficient Synthesis of Indenopyrazolones via a One-Pot Multicomponent Reaction,” Polycyclic Aromatic Compounds (2019): 1–9.
   Web of Science ®Google Scholar
• E. Ruijter, and R. V. A. Orru, “Multicomponent Reactions - opportunities for the pharmaceutical industry,” Drug Discovery Today. Technologies 10, no. 1 (2013): e15–e20.
   PubMedGoogle Scholar
• C. K. Jadhav, A. S. Nipate, A. V. Chate, A. P. Patil, and C. H. Gill, “Ionic Liquid Catalyzed One‐Pot Multi‐Component Synthesis of Fused Pyridine Derivatives: A Strategy for Green and Sustainable Chemistry,” Journal of Heterocyclic Chemistry 57, no. 12 (2020): 4291–303. jhet.4135.
   Web of Science ®Google Scholar
• C. K. Jadhav, A. S. Nipate, A. V. Chate, V. S. Dofe, J. N. Sangshetti, V. M. Khedkar, and C. H. Gill, “Rapid Construction of Substituted Dihydrothiophene Ureidoformamides at Room Temperature Using Diisopropyl Ethyl Ammonium Acetate: A Green Perspective,” ACS Omega 5, no. 45 (2020): 29055–67.
   PubMed Web of Science ®Google Scholar
• R. Ghorbani-Vaghei, F. Rahmatpour, N. Sarmast, J. Mahmoudi, and A. Shahriari, “DABCO as a Green Catalyst for the Synthesis of Pyranoquinoline Derivatives,” Canadian Journal of Chemistry 95, no. 5 (2017): 601–4.
   Web of Science ®Google Scholar
• R. Pagadala, S. Maddila, S. Rana, and S. B. Jonnalagadda, “Ce–Zr/SiO2: A Versatile Reusable Heterogeneous Catalyst for Three-Component Synthesis and Solvent Free Oxidation of Benzyl Alcohol,” RSC Advances 4, no. 13 (2014): 6602.
   Web of Science ®Google Scholar
• A. Weyesa, and E. Mulugeta, “Recent Advances in the Synthesis of Biologically and Pharmaceutically Active Quinoline and Its Analogues: A Review,” RSC Advances 10, no. 35 (2020): 20784–93.
   PubMed Web of Science ®Google Scholar
• X.-F. Shang, S. L. Morris-Natschke, Y.-Q. Liu, X. Guo, X.-S. Xu, M. Goto, J.-C. Li, G.-Z. Yang, and K.-H. Lee, “Biologically Active Quinoline and Quinazoline Alkaloids Part I,” Medicinal Research Reviews 38, no. 3 (2018): 775–828.
   PubMed Web of Science ®Google Scholar
• R. A. Mekheimer, M. A. Al-Sheikh, H. Y. Medrasi, and K. U. Sadek, “Advancements in the Synthesis of Fused Tetracyclic Quinoline Derivatives,” RSC Advances 10, no. 34 (2020): 19867–935.
   PubMed Web of Science ®Google Scholar
• K. D. Upadhyay, N. M. Dodia, R. C. Khunt, R. S. Chaniara, and A. K. Shah, “Synthesis and Biological Screening of Pyrano[3,2-c]quinoline Analogues as Anti-inflammatory and Anticancer Agents ,” ACS Medicinal Chemistry Letters 9, no. 3 (2018): 283–8.
   PubMed Web of Science ®Google Scholar
• I.-S. Chen, I.-W. Tsai, C.-M. Teng, J.-J. Chen, Y.-L. Chang, F.-N. Ko, M. C. Lu, and J. M. Pezzuto, “Pyranoquinoline Alkaloids from Zanthoxylum Simulans,” Phytochemistry 46, no. 3 (1997): 525–9.
   Web of Science ®Google Scholar
• H. K. Wabo, P. Tane, J. D. Connolly, C. C. Okunji, B. M. Schuster, and M. M. Iwu, “Tabouensinium Chloride, a Novel Quaternary Pyranoquinoline Alkaloid from Araliopsis Tabouensis,” Natural Product Research 19, no. 6 (2005): 591–5.
   PubMed Web of Science ®Google Scholar
• J. P. Michael, “Quinoline, Quinazoline and Acridone Alkaloids,” Natural Product Reports 24, no. 1 (2007): 223–46.
   PubMed Web of Science ®Google Scholar
• C. Ito, M. Itoigawa, A. Furukawa, T. Hirano, T. Murata, N. Kaneda, Y. Hisada, K. Okuda, and H. Furukawa, “Quinolone Alkaloids with Nitric Oxide Production Inhibitory Activity from Orixa Japonica,” Journal of Natural Products 67, no. 11 (2004): 1800–3.
   PubMed Web of Science ®Google Scholar
• D. Mabire, S. Coupa, C. Adelinet, A. Poncelet, Y. Simonnet, M. Venet, R. Wouters, A. S. J. Lesage, L. Van Beijsterveldt, and F. Bischoff, “Synthesis, structure-activity relationship, and receptor pharmacology of a new series of quinoline derivatives acting as selective, noncompetitive mGlu1 antagonists,” Journal of Medicinal Chemistry 48, no. 6 (2005): 2134–53. [15771457]
   PubMed Web of Science ®Google Scholar
• M. Sekar, and K. J. R. Prasad, “Synthesis of Some Novel 2-Oxo‐Pyrano(2,3-b)- and 2-Oxo‐Pyrido(2,3-b)Quinoline Derivatives as Potential Antimalarial, Diuretic, Clastogenic and Antimicrobial Agents,” Journal of Chemical Technology & Biotechnology 72, no. 1 (1998): 50–4.
   PubMed Web of Science ®Google Scholar
• M. J. McLaughlin, and R. P. Hsung, “Total Syntheses of Pyranoquinoline Alkaloids: Simulenoline, Huajiaosimuline, and (+/-)-7-demethoxyzanthodioline,” The Journal of Organic Chemistry 66, no. 3 (2001): 1049–53.
   PubMed Web of Science ®Google Scholar
• H. Cairns, D. Cox, K. J. Gould, A. H. Ingall, and J. L. Suschitzky, “New Antiallergic Pyrano [3,2-g]Quinoline-2,8-Dicarboxylic Acids with Potential for the Topical Treatment of Asthma,” Journal of Medicinal Chemistry 28, no. 12 (1985): 1832–42.
   PubMed Web of Science ®Google Scholar
• R. Watpade, A. Bholay, and R. Toche, “Synthesis of New Pyrano-Fused Quinolines as Antibacterial and Antimicrobial Agents,” Journal of Heterocyclic Chemistry 54, no. 6 (2017): 3434–9.
   Web of Science ®Google Scholar
• A. M. El-Agrody, E. S. A. E. H. Khattab, A. M. Fouda, and A. M. Al-Ghamdi, “Synthesis and Antitumor Activities of Certain Novel 2-Amino-9-(4-Halostyryl)-4H-Pyrano[3,2-h]Quinoline Derivatives,” Medicinal Chemistry Research 21, no. 12 (2012): 4200–13.
   Web of Science ®Google Scholar
• J. Marco-Contelles, R. León, M. G. López, A. G. García, and M. Villarroya, “Synthesis and Biological Evaluation of New 4H-Pyrano[2,3-b]Quinoline Derivatives That Block Acetylcholinesterase and Cell Calcium Signals, and Cause Neuroprotection against Calcium Overload and Free Radicals,” European Journal of Medicinal Chemistry 41, no. 12 (2006): 1464–9.
   PubMed Web of Science ®Google Scholar
• A. A. A. Hafez, and N. M. Nahas, “Synthesis and Antifungal Testing of Some New Tricyclic Heterocyclic Quinolines,” Heterocyclic Communications 11, no. 6 (2005): 495–504.
   Web of Science ®Google Scholar
• J. P. Michael, “Quinoline, Quinazoline and Acridone Alkaloids,” Natural Product Reports 20, no. 5 (2003): 476–93.
   PubMed Web of Science ®Google Scholar
• O. Afzal, S. Kumar, M. R. Haider, M. R. Ali, R. Kumar, M. Jaggi, and S. Bawa, “A Review on Anticancer Potential of Bioactive Heterocycle Quinoline,” European Journal of Medicinal Chemistry 97, (2015): 871–910.
   PubMed Web of Science ®Google Scholar
• A. V. Chate, A. S. Kulkarni, C. K. Jadhav, A. S. Nipte, and G. M. Bondle, “Multicomponent Reactions and Supramolecular Catalyst: A Perfect Synergy for Eco‐Compatible Synthesis of Pyrido[2,3‐ d] Pyrimidines in Water,” Journal of Heterocyclic Chemistry 57, no. 5 (2020): 2184–93.
   Web of Science ®Google Scholar
• K. Tungala, P. Adhikary, V. Azmeera, K. Kumar, and S. Krishnamoorthi, “Dendritic Star Polymer of Polyacrylamide Based on a β-Cyclodextrin Trimer: A Flocculant and Drug Vehicle,” New Journal of Chemistry 41, no. 2 (2017): 611–8.
   Web of Science ®Google Scholar
• V. B. Yadav, P. Rai, H. Sagir, A. Kumar, and I. R. Siddiqui, “A Green Route for the Synthesis of Pyrrolo[2,3- d] Pyrimidine Derivatives Catalyzed by β-Cyclodextrin,” New Journal of Chemistry 42, no. 1 (2018): 628–33.
   Web of Science ®Google Scholar
• M. Murugan, R. Rajamohan, A. Anitha, and M. Fatiha, “Non-Covalent Bonding Interaction between Primaquine as Guest and 2-(Hydroxypropyl)-β-Cyclodextrin as Host,” Polycyclic Aromatic Compounds, (2020): 1–18.
   Web of Science ®Google Scholar
• G. S. Kumar, M. Zeller, M. A. Frasso, and K. J. R. Prasad, “InCl 3 Promoted Synthesis of Pyrano[3,2- h] Quinolines via Microwave Irradiation,” Journal of Heterocyclic Chemistry 52, no. 3 (2015): 926–30.
   Web of Science ®Google Scholar
• S. Bandaru, R. K. Majji, S. Bassa, P. N. Chilla, R. Yellapragada, S. Vasamsetty, R. K. Jeldi, R. B. Korupolu, and P. D. Sanasi, “Magnetic Nano Cobalt Ferrite Catalyzed Synthesis of 4<i>H</i>-Pyrano[3,2-<i>h</i>]Quinoline Derivatives under Microwave Irradiation,” Green and Sustainable Chemistry 06, no. 02 (2016): 101–9.
   Google Scholar
• I. V. Magedov, M. Manpadi, M. A. Ogasawara, A. S. Dhawan, S. Rogelj, S. Van Slambrouck, W. F. A. Steelant, N. M. Evdokimov, P. Y. Uglinskii, E. M. Elias, et al. “Structural Simplification of Bioactive Natural Products with Multicomponent Synthesis. 2. antiproliferative and Antitubulin Activities of Pyrano[3,2-c]Pyridones and Pyrano[3,2-c]Quinolones,” Journal of Medicinal Chemistry 51, no. 8 (2008): 2561–70.
   PubMed Web of Science ®Google Scholar
• X. Wang, Z. Zeng, D. Shi, X. Wei, and Z. Zong, “One‐Step Synthesis of 2‐Amino‐3‐Cyano‐4‐ Aryl‐1,4,5,6‐Tetrahydropyrano[3,2‐ c] Quinolin‐5‐One Derivatives Using KF–Al 2 O 3 as Catalyst,” Synthetic Communications 34, no. 16 (2004): 3021–7.
   Web of Science ®Google Scholar
• M. Goudar, H. Jayadevappa, A. Sudhakara, and K. Mahadevan, “Imino Diels-Alder Reactions: Efficient Synthesis of Pyrano and Furanoquinolines Catalyzed by Antimony (III) Sulfate,” Letters in Organic Chemistry 5, no. 8 (2008): 628–32.
   Web of Science ®Google Scholar
• M. A. Ibrahim, H. M. Hassanin, Y. A.-A. Gabr, and Y. A.-S. Alnamer, “Novel Heterocyclic Derivatives of Pyrano[3,2-c]Quinolinone from 3-(1-ethy1-4-Hydroxy-2-Oxo-2(1H)-Quinolin-3-yl)-3-Oxopropanoic Acid,” European Journal of Chemistry 1, no. 3 (2010): 195–9.
   Google Scholar
• A. Romdhane, and H. Ben. Jannet, “Synthesis of New Pyran and Pyranoquinoline Derivatives,” Arabian Journal of Chemistry 10, (2017): S3128–S34.
   Google Scholar
• Y. Ma, C. Qian, M. Xie, and J. Sun, “Lanthanide Chloride Catalyzed Imino Diels − Alder Reaction. One-Pot Synthesis of Pyrano[3,2- c] - and Furo[3,2- c] Quinolines,” The Journal of Organic Chemistry 64, no. 17 (1999): 6462–7.
   Web of Science ®Google Scholar
• A. S. Nipate, C. K. Jadhav, A. V. Chate, K. S. Taur, and C. H. Gill, “β‐Cyclodextrin Catalyzed Access to Fused 1,8‐Dihydroimidazo[2,3‐ b] Indoles via One‐Pot Multicomponent Cascade in Aqueous Ethanol: Supramolecular Approach toward Sustainability,” Journal of Heterocyclic Chemistry 57, no. 2 (2020): 820–9.
   Web of Science ®Google Scholar
• S. V. Akolkar, N. D. Kharat, A. A. Nagargoje, D. D. Subhedar, and B. B. Shingate, “Ultrasound-Assisted β-Cyclodextrin Catalyzed One-Pot Cascade Synthesis of Pyrazolopyranopyrimidines in Water,” Catalysis Letters 150, no. 2 (2020): 450–60.
   Web of Science ®Google Scholar