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Articles

Solvent-Free One-Pot Synthesis of 1,8-Dioxo-Decahydroacridines by a [Et3NH][HSO4] Catalyzed Multicomponent Reaction

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Pages 329-337 | Received 05 May 2016, Accepted 25 Jun 2016, Published online: 12 Dec 2016

References

  • Gamage, S. A., J. A. Spicer, G. J. Atwell, G. J. Finlay, B. C. Baguley, and W. A. Denny. “Structure-activity Relationships for Substituted Bis(acridine-4-carboxamides): A New Class of Anticancer Agents.” J. Med. Chem. 42 ( 1999): 2383–93.
  • Antonini, I., P. Polucci, L. R. Kelland, E. Menta, N. Pescalli, and S. Martelli. “2,3-Dihydro-1H,7H-pyrimido[5,6,1-de]acridine-1,3,7-trione Derivatives, A Class of Cytotoxic Agents Active on Multidrug-Resistant Cell Lines: Synthesis, Biological Evaluation, and Structure-Activity Relationships.” J. Med. Chem. 42 ( 1999): 2535–41.
  • Gallo, S., S. Atifi, A. Mohamoud, C. Santelli-Rouvier, K. Wolfart, J. Molnar, and J. Barbe. “Synthesis of Aza Mono, Bi and Tricyclic Compounds. Evaluation of Their Anti MDR Activity.” Eur. J. Med. Chem. 38 ( 2003): 19–26.
  • Ngadi, L., A. M. Galy, J. P. Galy, J. Barbe, A. Cremieux, J. Chevalier, and D. Sharples. “Some New 1-Nitro Acridine Derivatives as Antimicrobial Agents.” Eur. J. Med. Chem. 25 ( 1990): 67–70.
  • Shanmugasundaram, P., P. Murugan, V. T. Ramakrishnan, N. Srividya, and P. Ramamurthy. “Synthesis of Acridinedione Derivatives as Laser Dyes.” Heteroatom Chem. 7 ( 1996): 17–22.
  • Murugan, P., P. Shanmugasundaram, V. T. Ramakrishnan, B. Venkatachalpathy, N. Srividya, P. Ramamurthy, K. Gunasekaran, and P. Velmurugan. “Synthesis and Laser Properties of 9-Alkyl-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione Derivatives.” J. Chem. Soc. Perkin Trans. 2 ( 1998): 999–1004.
  • Nikpassand, M., M. Mamaghani, and K. Tabatabaeian. “An Efficient One-Pot Three-Component Synthesis of Fused 1,4-Dihydropyridines Using HY-zeolite.” Molecules 14 ( 2009): 1468–74.
  • Shi, D. Q., S. N. Ni, F. Yang, J. W. Shi, G. L. Dou, X. Y. Li, and X. S. Wang. “An Efficient Synthesis of Polyhydroacridine Derivatives by the Three-Component Reaction of Aldehydes, Amines and Dimedone in Ionic Liquid.” J. Heterocyclic Chem. 45 ( 2008): 653–60.
  • Balalaie, S., F. Chadegani, F. Darviche, and H. R. Bijanzadeh. “One-Pot Synthesis of 1,8-Dioxo-decahydroacridine Derivatives in Aqueous Media.” Chin. J. Chem. 27 ( 2009): 1953–6.
  • Zare, L. and M. Nikpassand. “Multicomponent Synthesis of Dihydropyridines Catalyzed by L-Proline.” Chin. Chem. Lett. 22 ( 2011): 531–4.
  • Wang, X. S., D. Q. Shi, Y. F. Zhang, S. H. Wang, and S. J. Tu. “Synthesis of 9-Arylpolyhydroacridine in Water Catalyzed by Triethylbenzylammonium Chloride (TEBA).” Chin. J. Organic Chem. 24 ( 2004): 430–2.
  • Davoodnia, A., A. Khojastehnezhad, and N. Tavakoli-Hoseini. “Carbon-Based Solid Acid as an Efficient and Reusable Catalyst for the Synthesis of 1,8-Dioxodecahydroacridines under Solvent-Free Conditions.” Bull. Korean Chem. Soc. 32 ( 2011): 2243–8.
  • Fan, X., Y. Li, X. Zhang, G. Qu, and J. Wang. “An Efficient and Green Preparation of 9-Arylacridine-1,8-dione Derivatives.” Heteroatom Chem. 18 ( 2007): 786–90.
  • Rostamizadeh, S., A. Amirahmadi, N. Shadjou, and A. M. Amani. “MCM-41-SO3H as a Nanoreactor for the One-Pot, Solvent-Free Synthesis of 1,8-Dioxo-9-aryl Decahydroacridines.” J. Heterocyclic Chem. 49 ( 2012): 111–5.
  • Rad-Moghadam, K., S. C. Azimi. “Mg(BF4)2 Doped in [BMIm][BF4]: A Homogeneous Ionic Liquid-Catalyst for Efficient Synthesis of 1,8-Dioxo-octahydroxanthenes, Decahydroacridines and 14-Aryl-14H-dibenzo[a,j]xanthenes.” J. Mol. Catalysis A: Chem. 363–4 ( 2012): 465–9.
  • Wei, J. H., Y. Q. Li, X. Z. Lian, and M. Y. Zhou. “Synthesis of 9-Arylpolyhydroacridine Promoted by Ionic Liquid under Solvent-Free Condition.” Chin. Chem. Lett. 17 ( 2006): 874–6.
  • Kidwai, M., and D. Bhatnagar. “Polyethylene Glycol-Mediated Synthesis of Decahydroacridine-1, 8-diones Catalyzed by Ceric Ammonium Nitrate.” Chem. Pap. 64 ( 2010): 825–8.
  • Rezaei, R., 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 Commun. 19 ( 2013): 57–63.
  • Davoodnia, A., A. Zare-Bidaki, and H. Behmadi. “A Rapid and Green Method for Solvent-Free Synthesis of 1,8-Dioxodecahydroacridines Using Tetrabutylammonium Hexatungstate as a Reusable Heterogeneous Catalyst.” Chin. J. Catalysis 33 ( 2012): 1797–801.
  • Hong, M. and G. Xiao. “FSG-Hf(NPf2)4 Catalyzed, Environmentally Benign Synthesis of 1,8-Dioxo-decahydroaridines in Water-Ethanol.” J. Fluorine Chem. 144 ( 2012): 7–9.
  • Mohammadi Ziarani G., S. Mousavi, N. Lashgari, A. Badiei, M. Shakiba. “Application of Sulfonic Acid Functionalized Nanoporous Silica (SBA-Pr-SO3H) in the Green One-Pot Synthesis of Polyhydroacridine Libraries.” Iran. J. Chem. Chem. Eng. 32 ( 2013): 9–16.
  • Mohammadi Ziarani G., A. Badiei, M. Hassanzadeh, S. Mousavi. “Synthesis of 1,8-Dioxo-decahydroacridine Derivatives Using Sulfonic Acid Functionalized Silica (SiO2-Pr-SO3H) under Solvent Free Conditions.” Arab. J. Chem. 7 ( 2014): 335–9.
  • Khodja, I. A., W. Ghalem, Z. I. Dehimat, R. Boulcina, B. Carboni, and A. Debache. “Solvent-Free Synthesis of Dihydropyridines and Acridinediones via a Salicylic Acid-Catalyzed Hantzsch Multicomponent Reaction.” Synth. Commun. 44 ( 2014): 959–67.
  • Borhade, A. V., B. K. Uphade, and A. G. Gadhave. “Efficient, Solvent-Free Synthesis of Acridinediones Catalyzed by CdO Nanoparticles.” Res. Chem. Intermediates 41 ( 2015): 1447–58.
  • Wang, C., L. Guo, H. Li, Y. Wang, J. Weng, and L. Wu. “Preparation of Simple Ammonium Ionic Liquids and Their Application in the Cracking of Dialkoxypropanes.” Green Chem. 8 ( 2006): 603–7.
  • Ganeshpure, P. A., G. George, and J. Das. “Brønsted Acidic Ionic Liquids Derived from Alkylamines as Catalysts and Mediums for Fischer Esterification: Study of Structure-Activity Relationship.” J. Mol. Catalysis A: Chem. 279 ( 2008): 182–6.
  • Wang, C., W. Zhao, H. Li, and L. Guo. “Solvent-Free Synthesis of Unsaturated Ketones by the Saucy-Marbet Reaction Using Simple Ammonium Ionic Liquid as a Catalyst.” Green Chem. 11 ( 2009): 843–7.
  • Kermani, E. T., H. Khabazzadeh, and T. Jazinizadeh. “Friedländer Synthesis of Poly-Substituted Quinolines in the Presence of Triethylammonium Hydrogen Sulfate [Et3NH][HSO4] as a Highly Efficient, and Cost Effective Acidic Ionic Liquid Catalyst.” J. Heterocyclic Chem. 48 ( 2011): 1192–6.
  • Rajendran, A., D. Raghupathy, and M. Priyadarshini. “A Domino Green Synthesis of Bis(indolyl)methanes Catalyzed by Ionic Liquid [Et3NH][HSO4].” Int. J. Chem. Tech. Res. 3 ( 2011): 298–302.
  • Khabazzadeh, H., E. T. Kermani, and T. Jazinizadeh. “An Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Catalyzed by Molten [Et3NH][HSO4].” Arab. J. Chem. 5 ( 2012): 485–8.
  • Siddiqui, Z. N. and K. Khan. “[Et3NH][HSO4]-Catalyzed Efficient, Eco-Friendly, and Sustainable Synthesis of Quinoline Derivatives via Knoevenagel Condensation.” ACS Sustainable Chem. Eng. 2 ( 2014): 1187–94.
  • Shaterian, H. R., M. Mohammadnia, and F. Moradi. “Acidic Ionic Liquids Catalyzed Three-Component Synthesis of 12-Aryl-12H-indeno[1,2-b]naphtho[3,2-e]pyran-5,11, 13-trione and 13-Aryl-indeno[1,2-b]naphtha[1,2-e] pyran-12(13H)-one Derivatives.” J. Mol. Liq. 172 ( 2012): 88–92.
  • Zhou, Z., X. Deng, and X. Hu. “[Et3NH][HSO4] Catalyzed One-Pot Synthesis of 14-Aryl-14H-dibenzo[a,j]xanthenes under Solvent-Free Conditions.” Iran. J. Catalysis 3 ( 2013): 237–42.
  • Zhou, Z. and X. Deng. “[Et3NH][HSO4] Catalyzed Efficient and Green Synthesis of 1,8-Dioxo-octahydroxanthenes.” J. Mol. Catalysis A: Chem. 367 ( 2013): 99–102.
  • Deng, X., Z. Zhou, A. Zhang, and G. Xie. “Brønsted Acid Ionic Liquid [Et3NH][HSO4] as Efficient and Reusable Catalyst for the Synthesis of 2,4,5-Triaryl-1H-imidazoles.” Res. Chem. Intermediates 39 ( 2013): 1101–8.
  • Zhang, J., Y. Zhang, and Z. Zhou. “Hydroxyl Ammonium Ionic Liquid Catalyzed Simple and Efficient Synthesis of 5-Arylidene-2,4-thiazolidinediones under Solvent-Free Conditions.” Green Chem. Lett. Rev. 7 ( 2014): 90–4.
  • Zhou, Z. and Y. Zhang. “An Efficient And Green One-Pot Three-Component Synthesis of 4,4′-(Arylmethylene)bis(1H-pyrazol-5-ol)s Catalyzed by 2-Hydroxy Ethylammonium Propionate.” Green Chem. Lett. Rev. 7 ( 2014): 17–23.
  • Suárez, M., A. Loupy, E. Salfrán, L. Morán, and E. Rolando. “Synthesis of Decahydroacridines under Microwaves Using Ammonium Acetate Supported on Alumina.” Heterocycles 51 ( 1999): 21–7.
  • Martin, N., M. Quinteiro, C. Seoane, L. Soto, A. Mora, M. Suarez, E. Ockoa, and A. Morales. “Synthesis and Conformational Study of Acridine Derivatives Related to 1,4-Dihydropyridines.” J. Heterocyclic Chem. 32 ( 1995): 235–8.
  • Garcia, M. T., N. Gathergood, and P. J. Scammells. “Biodegradable Ionic Liquids: Part II. Effect of the Anion and Toxicology.” Green Chem. 7 ( 2005): 9–14.
  • Gathergood, N., M. T. Garcia, and P. J. Scammells. “Biodegradable Ionic Liquids: Part I. Concept, Preliminary Targets and Evaluation.” Green Chem. 6 ( 2004): 166–75.
  • Wasserscheid, P., R. Hal, and A. Bosmann. “1-n-Butyl-3-methylimidazolium ([bmim]) Octylsulfate-an Even ‘Greener’ Ionic Liquid.” Green Chem. 4 ( 2002): 400–4.

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