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Original Articles

A One-pot Multicomponent Synthesis of Pyrroloacridine-1(2H)-one and 1,8-Dioxodecahydroacridine Derivatives Catalyzed by Salicylic Acid in Polyethylene Glycol

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Pages 774-783 | Received 24 Dec 2017, Accepted 19 May 2018, Published online: 02 Nov 2018

References

  • Nathalie Dias, Herevé Vezin, Amélie Lansiaux, and Christian Bailly, “Topoisomerase Inhibitors of Marine Origin and Their Potential Use as Anticancer Agents,” DNA Binders and Related Subjects 253 (2005): 89–108.
  • Wayne D. Inman, Mark O'Neill-Johnson, and Phillip Crews. “Novel Marine Sponge Alkaloids. 1. Plakinidine A and B, Anthelmintic Active Alkaloids from a Plakortis Sponge,” Journal of the American Chemical Society 112 (1990): 1–4.
  • Mark Wainwright, “Acridine—A Neglected Antibacterial Chromophore,” Journal of Antimicrobial Chemotherapy 47 (2001): 1–13.
  • Philip C. Schofield, Iain G. Robertson, James W. Paxton, Michael R. McCrystal, Barrie D. Evans, Philp Kestell, and B. C. Baguley. “Metabolism of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide in Cancer Patients Undergoing a Phase I Clinical Trial.” Cancer Chemotherapy and Pharmacology 44 (1999): 51–8.
  • David Greenwood, “Conflicts of Interest: The Genesis of Synthetic Antimalarial Agents in Peace and War,” Journal of Antimicrobial Chemotherapy 36 (1995): 857–72.
  • Peter J. McCarthy, Tara P. Pitts, Geewananda P. Gunawardana, Michelle Kelly-Borges, and Shirley A. Pomponi, “Antifungal Activity of Meridine, a Natural Product from the Marine Sponge Corticium sp.,” Journal of Natural Products 55 (1992): 1664–8.
  • N. Srividya, P. Ramamurthy, P. Shanmugasundaram, and V. T. Ramakrishnan. “Synthesis, Characterization, and Electrochemistry of Some acridine-1,8-dione Dyes.” The Journal of Organic Chemistry 61 (1996): 5083–89.
  • Paule A. Clarke, Soraia Santos, and William H. Martin. “Combining Pot, Atom and Step Economy (PASE) in Organic Synthesis. Synthesis of tetrahydropyran-4-ones,” Green Chemistry 9 (2007): 438–40.
  • Eelco Ruijter, Rachel Scheffelaar, and Romano V. Orru. “Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity,” Angewandte Chemie International Edition 50 (2011): 6234–46.
  • David W. MacMillan, “The Advent and Development of Organocatalysis,” Nature 455, no. 7211 (2008): 304–8.
  • I. Raskin, “Role of Salicylic Acid in Plants,” Annual Review of Plant Biology 43 (1992): 439–63.
  • Mazaahir Kidwai and Divya Bhatnagar. “Ceric Ammonium Nitrate (CAN) Catalyzed Synthesis of N-substituted decahydroacridine-1,8-diones in PEG,” Tetrahedron Letters 51 (2010): 2700–03.
  • Masoud Nasr-Esfahani, Zahra Rafiee, and Hassan Kashi, “Nanoparticles Tungstophosphoric Acid Supported on Polyamic Acid: Catalytic Synthesis of 1,8-dioxo-decahydroacridines and bulky bis (1,8-dioxo-decahydroacridine) s.,” Journal of the Iranian Chemical Society 13 (2016): 1449–61.
  • Nourallah Hazeri, Amin Masoumnia, Malek T. Mghsoodlou, Sajjad Salahi, Mehrnoosh Kangani, Samira Kianpour, Shiva Kiaee, and Jasem Abonajmi. “Acetic Acid as an Efficient Catalyst for Synthesis of 1, 8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines,” Research on Chemical Intermediates 41 (2015): 4123–31.
  • K. Venkatesan, S. S. Pujari, and K. V. Srinivasan, “Proline-catalyzed simple and efficient synthesis of 1, 8-dioxo-decahydroacridines in aqueous ethanol medium,” Synthetic Communications 39 (2008): 228–241.
  • B. Das, P. Thirupathi, I. Mahender, V. S. Reddy, and Y. K. Rao, “Amberlyst-15: An Efficient Reusable Heterogeneous Catalyst for the Synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-Decahydroacridines,” Journal of Molecular Catalysis A: Chemical 247 (2006): 233–39.
  • M. A. Zolfigol, N. Bahrami-Nejad, and S. Baghery, “A Convenient Method for the Synthesis of 1,8-dioxodecahydroacridine Derivatives Using 1-methylimidazolium tricyanomethanide {[HMIM]C(CN)3} as a Nanostructured Molten Salt Catalyst,” Journal of Molecular Liquids 218 (2016): 558–64
  • M. A. Ghasemzadeh, J. Safaei-Ghomi, and H. Molaei, “Fe3O4 nanoparticles: As an Efficient, Green and Magnetically Reusable Catalyst for the One-Pot Synthesis of 1,8-dioxo-decahydroacridine Derivatives Under Solvent-Free Conditions,” Comptes Rendus Chimie 15 (2012): 969–74.
  • J. J. Xia and K. H. Zhang, “Synthesis of N-Substituted Acridinediones and Polyhydroquinoline Derivatives in Refluxing Water,” Molecules 17 (2012): 5339–45.
  • K. B. Ramesh and M. A. Pasha, “Study on One-Pot Four-Component Synthesis of 9-aryl-hexahydro-acridine-1, 8-diones using SiO2–I as a New Heterogeneous Catalyst and Their Anticancer Activity,” Bioorganic & Medicinal Chemistry Letters 24 (2014): 3907–13.
  • Minoo Dabiri, Mostafa Baghbanzadeh, Elham Arzroomchilar, “1-Methylimidazolium Triflouroacetate ([Hmim] TFA): An Efficient Reusable Acidic Ionic Liquid for the Synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines,” Catalysis Communications 9 (2008): 939–42.
  • S. Pradhan and B. G. Mishra. “Catalytic Application of SO42−/Fe–ZrO2 Nanoparticles Synthesized by a Urea Hydrolysis Method for Environmentally Benign One Pot Synthesis of 1, 8-dioxodecahydroacridines,” RSC Advances 5 (2015): 86179–90.
  • A. Khojastehnezhad, M. Rahimizadeh, H. Eshghi, F. Moeinpour, and M. Bakavoli, “Ferric Hydrogen Sulfate Supported on Silica-Coated Nickel Ferrite Nanoparticles as New and Green Magnetically Separable Catalyst for 1,8 dioxodecahydroacridine Synthesis,” Chinese Journal of Catalysis 35 (2014): 376–82.
  • R. Vaid, M. Gupta, and V. K. Gupta, “Immobilization of Organofunctionalized Silica (SiMPTMS) with Biphenyl-2, 2′-dioic acid and Investigation of its Catalytic Property for One-Pot Tandem Synthesis of Acridine-1, 8-dione derivatives,” Journal of the Iranian Chemical Society 14 (2017): 2199–210.
  • H. Wang, L. Li, W. Lin, P. Xu, Z. Huang, and D. Shi, “ An Efficient Synthesis of pyrrolo[2,3,4-kl]acridin-1-One Derivatives Catalyzed by L-proline,” Organic Letters 14 (2012): 4598–601.
  • L. L. Li, H. Y. Wang, W. Lin, Z. B. Huang, and D. Q. Shi, “Improved and Efficient Synthesis of Pyrrolo [2,3,4‐kl] acridin‐1‐one Derivatives under Ultrasound Irradiation,” Journal of Heterocyclic Chemistry 51 (2014): 1778–84.
  • C. Cao, C. Xu, W. Lin, X. Li, M. Hu, J. Wang, Z. Huang, D. Shi, and Y. Wang, “Microwave-Assisted Improved Synthesis of pyrrolo [2,3,4-kl] acridine and dihydropyrrolo [2,3,4-kl] acridine Derivatives Catalyzed by Silica Sulfuric Acid,” Molecules 18 (2013): 1613–25.
  • Z. Karimi-Jaberi and A. Jaafarizadeh, “One-Pot, Three-Component Reaction of Dimedone, Amines, and Isatin in the Presence of tris(hydrogensulfato)boron: Synthesis of Pyrroloacridine Derivatives,” Research on Chemical Intermediates 41 (2015): 4913–18.
  • S. Ray, A. Bhaumik, M. Pramanik, and C. Mukhopadhyay, “Covalently Anchored Carboxylic Acid on Uniform Spherical Silica Nanoparticles with Narrow Slit Like Mesopores for the Synthesis of Pyrroloacridinones: CuI-Catalyzed Further C(sp3)–H oxyfunctionalization for C[double bond, Length as m-dash]O Formation,” RSC Advances 4 (2014): 15441–50.
  • M. A. Ghasemzadeh and B. Mirhosseini-Eshkevari, “Fe3O4@ Silica Sulfonic Acid Nanocomposite as a Magnetically Separable Catalyst for the Synthesis of 2-arylpyrrolo[2, 3,4-kl] acridin-1(2H)-ones,” Journal of Chemical Research 39 (2015): 380–86.
  • H. Kefayati, F. Narchin, and K. Rad-Moghadam, “An Unexpected Multicomponent Reaction Leading to 2-arylpyrrolo [2,3,4-kl]acridin-1(2H)-Ones,” Tetrahedron Letters 53 (2012): 4573–75.
  • Anshu Dandia, Amit Sharma, Vijay Parewa, Begraj Kumawat, Kuldeep S. Rathore, and Amit Sharma, “Amidic C–N Bond Cleavage of Isatin: Chemoselective Synthesis of pyrrolo [2,3,4-kl] acridin-1-Ones Using Ag NPs Decorated rGO Composite as an Efficient and Recoverable Catalyst Under Microwave Irradiation,” RSC Advances 5 (2015): 91888–902.
  • F. Noori Sadeh, N. Hazeri, M. T. Maghsoodlou, and M. Lashkari, “Eco-Friendly and Facile Approach Toward a One-Pot Synthesis of 2-Arylpyrrolo[2,3,4-kl] acridin-1(2H)-ones Catalyzed by Acetic Acid Under Solvent-Free Conditions,” Iranian Journal of Science and Technology, Transactions A: Science 42 (2018): 1253–1258.
  • M. Fatahpour, N. Hazeri, M. T. Maghsoodlou, and M. Lashkari, “A Green Approach for the One‐Pot, Three‐Component Synthesis of 2‐Arylpyrroloacridin‐1(2H)‐Ones using Lactic Acid as a Bio‐based Catalyst under Solvent‐Free Conditions,” Journal of the Chinese Chemical Society 64 (2017): 1071–78.
  • M. Fatahpour, N. Hazeri, M. T. Maghsoodlou, and M. Lashkari, “One-Pot Condensation Approach for Synthesis of Diverse Naphthopyranopyrimidines Utilizing Lactic Acid as Efficient and Eco-Friendly Catalyst,” Polycyclic Aromatic Compounds (2017). https://doi.org/https://doi.org/10.1080/10406638.2017.1326948
  • A. Thakur, P. L. Reddy, M. Tripathi, and D. S. Rawat, “Facile Construction of 3-indolochromenes and 3-indoloxanthenes via EDDF Catalyzed One-Pot Three Component Reactions,” New Journal of Chemistry 39 (2015): 6253–60.
  • B. Aday, Y. Yıldız, R. Ulus, S. Eris, F. Sen, and M. Kaya, “One-Pot, Efficient and Green Synthesis of Acridinedione Derivatives Using Highly Monodisperse Platinum Nanoparticles Supported with Reduced Graphene Oxide,” New Journal of Chemistry 40 (2016): 748–54.
  • Z. Q. Tang, Y. Chen, C. N. Liu, K. Y. Cai, and S. J. Tu, “A Green Procedure for the Synthesis of 1,8‐dioxodecahydroacridine Derivatives Under Microwave Irradiation in Aqueous Media Without Catalyst,” Journal of Heterocyclic Chemistry 47 (2010): 363–7.
  • O. I. E. Sabbagh, M. A. Shabaan, H. H. Kadry, and E. S. Al-Din, “Synthesis of New Nonclassical Acridines, Quinolines, and Quinazolines Derived from Dimedone for Biological Evaluation,” Archiv der Pharmazie 343 (2010): 519–27.
  • R. Rezaei, R. Khalifeh, M. Rajabzadeh, L. Dorosty, and M. M. Doroodmand, “Melamine-Formaldehyde Resin Supported H+-Catalyzed Three-Component Synthesis of 1,8-dioxo-decahydroacridine Derivatives in Water and Under Solvent-Free Conditions,” Heterocyclic Communications 19 (2013): 57–63.
  • L. L. Zhao and D. Teng, “ 10-(4-Chloro-phen-yl)-9-(4-fluoro-phen-yl)-3,3,6,6-tetra-methyl-3,4,6,7,9,10-hexa-hydro-acridine-1,8(2H,5H)-dione,” Acta Crystallographica Section E: Structure Reports Online 64 (2008): o1772–3.
  • S. S. Mansoor, K. Aswin, K. Logaiya, and S. P. N. Sudhan, “Aqua-mediated synthesis of acridinediones with reusable silica-supported sulfuric acid as an efficient catalyst,” Journal of Taibah University for Science 8 (2014): 265–75.

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