166
Views
7
CrossRef citations to date
0
Altmetric
Research Articles

Ultrasound Assisted and Aluminized Polyborate Prompted Green and Efficient One Pot Protocol for the Synthesis of Hexahydroquinolines

, , &
Pages 1375-1390 | Received 25 Mar 2020, Accepted 07 Jun 2020, Published online: 22 Jun 2020

References

  • (a) J. T. Li, Y. Yin, and M. X. Sun, “An Efficient One-Pot Synthesis of 2,3-Epoxyl-1,3-Diaryl-1-Propanone Directly from Acetophenones and Aromatic Aldehydes Under Ultrasound Irradiation ,”Ultrasonics Sonochemistry 17, no. 2 (2010): 363–6. (b) J. T. Li, Y. J. Bian, H. J. Zang, and T. S. Li, “Pinacol Coupling of Aromatic Aldehydes and Ketones Using Magnesium in Aqueous Ammonium Chloride under Ultrasound,” Synthetic Communications 32, no. 4 (2002): 547–51.
  • S. Allahyari, M. Haghighi, A. Ebadi, and S. Hosseinzadeh, “Ultrasound Assisted Co-Precipitation of Nanostructured CuO–ZnO–Al2O3 Over HZSM-5: Effect of Precursor and Irradiation Power on Nanocatalyst Properties and Catalytic Performance for Direct Syngas to DME,” Ultrasonics Sonochemistry 21, no. 2 (2014): 663–73.
  • M. Mirza-Aghayan, N. Ganjbakhsh, M. Molaee Tavana, and R. Boukherroub, “Ultrasound-Assisted Direct Oxidative Amidation of Benzyl Alcohols Catalyzed by Graphite Oxide,” Ultrasonics Sonochemistry 32 (2016) 37–43.
  • A. H. Xu, B. W. Zeiger, and K. S. Suslick, “Sonochemical Synthesis of Nanomaterials,” Chemical Society Reviews 42, no. 7 (2013): 2555–67.
  • G. Cravotto, and P. Cintas, “Power Ultrasound in Organic Synthesis: Moving Cavitational Chemistry from Academia to Innovative and Large-Scale Applications,” Chemical Society Reviews 35, no. 2 (2006): 180–96.
  • Z. Wang, L. Wang, Q. Chen, and M. He, “Rapid and Efficient Thiocyanation of Phenols, Indoles, and Anilines in 1,1,1,3,3,3-Hexafluoro-2-Propanol under Ultrasound Irradiation,” Synthetic Communications 48, no. 1 (2018): 76–84.
  • M. H. Geesi, O. Ouerghi, A. Elsanousi, A. Kaiba, and Y. Riadi, “Ultrasound-Assisted Preparation of Cu-Doped TiO2 Nanoparticles as a Nanocatalyst for Sonochemical Synthesis of Pyridopyrimidines,” Polycyclic Aromatic Compounds (2020): 1–11.
  • S. Sarhandi, L. Z. Fekri, and E. Vessally, “Ultrasound Assisted Chromatography-Free Synthesis of Triazolo [1,2-a]Indazole-Triones in the Presence of 1,4-Diazabicyclo[2.2.2] Octanium Diacetate as an Environmentally Friendly Green Media,” Polycyclic Aromatic Compounds (2019): 1–11.
  • M. Nikpassand, L. Z. Fekri, and K. Hematinezhad, “Ultrasound-Promoted Regioselective Synthesis of Pyrazolyl-Bis Coumarinyl Methanes Using Citric Acid as a Natural and Efficient Catalyst,” Polycyclic Aromatic Compounds 40, no. 2 (2020): 456–9.
  • M. H. Abdollahi-Basir, F. Shirini, H. Tajik, and M. A. Ghasemzadeh, “Zn (BDC)-(MOF): Introduction of a New Catalyst for the Synthesis Pyrimido[4,5-d]Pyrimidine Derivatives under Ultrasound Irradiation in the Absence of Solvent,” Polycyclic Aromatic Compounds (2019): 1–10.
  • Hugues Bienaymé, Chris Hulme, Gilles Oddon, and Philippe Schmitt, “Maximizing Synthetic Efficiency: Multi-Component Transformations Lead the Way,” Chemistry – A European Journal 6, no. 18 (2000): 3321–9.
  • B. Rotstein, S. Zaretsky, V. Rai, and A. Yudin, “Small Heterocycles in Multicomponent Reactions,” Chemical Reviews 114, no. 16 (2014): 8323–59.
  • J. Zhu, and H. Bienayme, Multicomponent Reactions (Weinheim: Wiley-VCH, 2010), 121–68.
  • H. Naeimi, and J. Didar, “Facile One-Pot Four Component Synthesis of Pyrido[2, 3-d: 6,5-d]Dipyrimidines Catalyzed by CuFe2O4 Magnetic Nanoparticles in Water,” Journal of Molecular Structure 1137 (2017): 626–33.
  • (a) H. Kiyani, and F. Ghorbani, “Boric Acid-Catalyzed Multi-Component Reaction for Efficient Synthesis of 4H-Isoxazol-Ones in Aqueous Medium,” Research on Chemical Intermediates 41, no. 5 (2015): 2653–64. (b) A. R. Moosavi-Zare, H. Afshar-Hezarkhani, and M. M. Rezaei, “Tandem Four Component Condensation Reaction of Aryl Aldehydes with Ethyl Acetoacetate, Malononitrile, and Hydrazine Hydrate Using Boric Acid in Water as an Efficient and Green Catalytic System,” Polycyclic Aromatic Compounds 40, no. 1 (2020): 150–9.
  • Rammohan Pal, “Boric Acid in Organic Synthesis: Scope and Recent Developments,” Arkivoc 2018, no. 1 (2018): 346–71.
  • S. Chandrasekhar, and K. Gopalaiah, “Beckmann Rearrangement of Ketoximes on Solid Metaboric Acid: A Simple and Effective Procedure,” Tetrahedron Letters 43, no. 13 (2002): 2455–7.
  • C. K. Khatri, M. S. Patil, and G. U. Chaturbhuj, “Sulfated Polyborate: Mild, Efficient and Eco-Friendly Catalyst for the Synthesis of 2, 3‐Dihydroquinazolin‐4 (1H)-Ones,” Journal of the Iranian Chemical Society 14, no. 8 (2017): 1683–9.
  • M. S. Patil, A. V. Palav, C. K. Khatri, and G. U. Chaturbhuj, “Rapid, Efficient and Solvent-Free Synthesis of (un)Symmetrical Xanthenes Catalyzed by Recyclable Sulfated Polyborate,” Tetrahedron Letters 58, no. 29 (2017): 2859–64.
  • V. P. Jejurkar, C. K. Khatri, G. U. Chaturbhuj, and S. Saha, “Environmentally Benign, Highly Efficient and Expeditious Solvent-Free Synthesis of Trisubstituted Methanes Catalyzed by Sulfated Polyborate,” ChemistrySelect 2, no. 35 (2017): 11693–6.
  • D. S. Rekunge, C. K. Khatri, and G. U. Chaturbhuj, “Sulfated Polyborate-Catalyzed Efficient and Expeditious Synthesis of (un)Symmetrical Ureas and Benzimidazolones,” Tetrahedron Letters 58, no. 45 (2017): 4304–7.
  • A. S. Mali, C. S. Potnis, and G. U. Chaturbhuj, “Aluminized Polyborate: A Novel Catalyst for the Multicomponent Solvent‐Free Synthesis of Alkyl 1,2,6‐Trisubstituted-4-[(Hetero) Arylamino]-1,2,5,6‐Tetrahydropyridine‐3‐Carboxylates,” Journal of the Iranian Chemical Society 15, no. 6 (2018): 1399–409.
  • C. Safak, and R. Simsek, “Fused 1,4-Dihydropyridines as Potential Calcium Modulatory Compounds,” Mini Reviews in Medicinal Chemistry 6, no. 7 (2006): 747–55.
  • R. Mannhold, B. Jablonka, W. Voigt, K. Sch€Onafinger, and E. Schraven, “Antagonism of Elnadipine Derivatives: Comparative SAR,” European Journal of Medicinal Chemistry 27, no. 3 (1992): 229–35.
  • T. R. Godfraind, R. Miller, and M. Wibo, “Calcium Antagonism and Calcium Entry Blockade,” Pharmacological Reviews 38, no. 4 (1986): 321–416.
  • A. Hantzsch, “Condensationsprodukte Aus Aldehydammoniak Und Ketonartigen Verbindungen,” Berichte der deutschen chemischen Gesellschaft 14, no. 2 (1881): 1637–8.
  • M. Z. Kassaee, H. Masrouri, and F. Movahedi, “ZnO-Nanoparticle-Promoted Synthesis of Polyhydroquninoline Derivatives via Multicomponent Hantzsch Reaction,” Monatshefte für Chemie – Chemical Monthly 141, no. 3 (2010): 317–22.
  • M. Saha, and A. K. Pal, “Palladium (0) Nanoparticles: An Efficient Catalyst for the One-Pot Synthesis of Polyhydroquinolines,” Tetrahedron Letters 52, no. 38 (2011): 4872–7.
  • M. Saha, T. S. Luireingam, T. Merry, and A. K. Pal, “Catalyst-Free, Knoevenagel–Michael Addition Reaction of Dimedone under Microwave Irradiation: An Efficient One-Pot Synthesis of Polyhydroquinoline Derivatives,” Journal of Heterocyclic Chemistry 50, no. 4 (2013): 941–4.
  • Mohammad Ali Zolfigol, Saeed Baghery, Ahmad Reza Moosavi-Zare, Seyed Mohammad Vahdat, Heshmatollah Alinezhad, and Mohammad Norouzi, “Synthesis of the First Nano Ionic Liquid 1-Methylimidazolium Trinitromethanide {[HMIM]C(NO2)3} and Its Catalytic Use for Hanztsch Four-Component Condensation,” RSC Advances 4, no. 101 (2014): 57662–70.
  • M. Abdollahi-Alibeik, and A. Rezaeipoor-Anari, “Fe3O4@B-MCM-41: A New Magnetically Recoverable Nanostructured Catalyst for the Synthesis of Polyhydroquinolines,” Journal of Magnetism and Magnetic Materials 398 (2016): 205–14.
  • M. Abdollahi-Alibeik, and A. Rezaeipoor-Anari, “MCM-41 Functionalized with B–F Bond: Preparation, Characterization and Catalytic Application in the Synthesis of Polyhydroquinolines,” Letters in Organic Chemistry 12, no. 9 (2015): 651–8.
  • M. Abdollahi‐Alibeik, and S. S. Hoseinikhah, “ClO4−/Zr-MCM-41 Nanoparticles Prepared at Mild Conditions: A Novel Solid Acid Catalyst for the Synthesis of Polyhydroquinolines,” Journal of the Iranian Chemical Society 13, no. 7 (2016): 1339–47.
  • S. Hashemi‐Uderji, M. Abdollahi‐Alibeik, and R. Ranjbar‐Karimi, “Fe3O4@FSM-16-SO3H as a Novel Magnetically Recoverable Nanostructured Catalyst: Preparation, Characterization and Catalytic Application,” Journal of Porous Materials 26 (2019): 467–80.
  • S. Hashemi-Uderji, M. Abdollahi-Alibeik, and R. Ranjbar-Karimi, “FSM-16-SO3H Nanoparticles as a Novel Heterogeneous Catalyst: Preparation, Characterization, and Catalytic Application in the Synthesis of Polyhydroquinolines,” Main Group Metal Chemistry 41, no. 3–4 (2018): 91–101.
  • M. A. Karimi Zarchi, and S. S. A. Darbandizadeh Mohammad Abadi, “Facile and Efficient Protocols for C–C and C–N Bond Formation Reactions Using a Superparamagnetic Palladium Complex as Reusable Catalyst,” Research on Chemical Intermediates 45, no. 5 (2019): 2605–39.
  • M. Tajbakhsh, E. Alaee, H. Alinezhad, M. Khanian, F. Jahani, S. Khaksar, P. Rezaee, and M. Tajbakhsh, “Titanium Dioxide Nanoparticles Catalyzed Synthesis of Hantzsch Esters and Polyhydroquinoline Derivatives,” Chinese Journal of Catalysis 33, no. 9–10 (2012): 1517–22.
  • S. Ko, M. N. V. Sastry, C. Lin, and C. F. Yao, “Molecular Iodine-Catalyzed One-Pot Synthesis of 4-Substituted-1, 4-Dihydropyridine Derivatives via Hantzsch Reaction,” Tetrahedron Letters 46, no. 34 (2005): 5771–4.
  • G. Sabitha, K. Arundhathi, K. Sudhakar, B. S. Sastry, and J. S. Yadav, “CeCl3–7H2O-Catalyzed One-Pot Synthesis of Hantzsch 1,4-Dihydropyridines at Room Temperature,” Synthetic Communications 39, no. 16 (2009): 2843–51.
  • J. Davarpanah, M. Ghahremani, and O. Najafi, “Synthesis of 1,4-Dihydropyridine and Polyhydroquinoline Derivatives via Hantzsch Reaction Using Nicotinic Acid as a Green and Reusable Catalyst,” Journal of Molecular Structure 1177 (2019): 525–35.
  • T. Tamoradi, A. Ghorbani-Choghamarani, M. Ghadermazi, and H. Veisi, “SBA-15@Glycine-M (M = Ni and Cu): Two Green, Novel and Efficient Catalysts for the One-Pot Synthesis of 5-Substituted Tetrazole and Polyhydroquinoline Derivatives,” Solid State Sciences 91 (2019): 96–107.
  • T. Momeni, M. M. Heravi, T. Hosseinnejad, M. Mirzaei, and V. Zadsirjan, “H5BW12O40-Catalyzed Syntheses of 1,4-Dihydropyridines and Polyhydroquinolines via Hantzsch Reaction: Joint Experimental and Computational Studies,” Journal of Molecular Structure 1199 (2020): 127011.
  • T. Tamoradi, M. Ghadermazi, and A. Ghorbani‐Choghamarani, “Synthesis of Polyhydroquinoline, 2,3-Dihydroquinazolin-4(1H)-One, Sulfide and Sulfoxide Derivatives Catalyzed by New Copper Complex Supported on MCM-41,” Catalysis Letters 149, no. 9 (2019): 2645–6.
  • A. Ghorbani‐Choghamarani, M. Mohammadi, L. Shiri, and Z. Taherinia, “Synthesis and Characterization of Spinel FeAl2O4 (Hercynite) Magnetic Nanoparticles and Their Application in Multicomponent Reactions,” Research on Chemical Intermediates 45, no. 11 (2019): 5705–23.
  • G. B. Dharma Rao, S. Nagakalyan, and G. K. Prasad, “Solvent-Free Synthesis of Polyhydroquinoline Derivatives Employing Mesoporous Vanadium Ion Doped Titania Nanoparticles as a Robust Heterogeneous Catalyst via the Hantzsch Reaction,” RSC Advances 7, no. 6 (2017): 3611–6.
  • P. Mondal, S. Chatterjee, P. Sarkar, A. Bhaumik, and C. Mukhopadhyay, “Preparation of DABCO-Based Acidic-Ionic-Liquid-Supported ZnO Nanoparticles and Their Application for Ecofriendly Synthesis of N-Aryl Polyhydroquinoline Derivatives,” ChemistrySelect 4, no. 40 (2019): 11701–10.
  • M. M. Heravi, M. Saeedi, N. Karimi, M. Zakeri, Y. S. Beheshtiha, and A. Davoodnia, “Brønsted Acid Ionic Liquid [(CH2)4SO3HMIM][HSO4] as Novel Catalyst for One-Pot Synthesis of Hantzsch Polyhydroquinoline Derivatives,” Synthetic Communications 40, no. 4 (2010): 523–9.
  • B. Sakram, B. Sonyanaik, K. Ashok, and S. Rambabu, “Polyhydroquinolines: 1-Sulfopyridinium Chloride Catalyzed an Efficient One-Pot Multicomponent Synthesis via Hantzsch Condensation under Solvent-Free Conditions,”Research on Chemical Intermediates 42, no. 10 (2016): 7651–8.
  • S. J. Yü, S. Wu, X. M. Zhao, and C. W. Lu, “Green and Efficient Synthesis of Acridine-1,8-Diones and Hexahydroquinolines via a KH2PO4 Catalyzed Hantzsch-Type Reaction in Aqueous Ethanol,” Research on Chemical Intermediates 43, no. 5 (2017): 3121–30.
  • S. C. Jadhvar, H. M. Kasraliker, S. V. Goswami, A. V. Chakrawar, and S. R. Bhusare, “One-Pot Synthesis and Evaluation of Anticancer Activity of Polyhydroquinoline Derivatives Catalyzed by [Msim]Cl,” Research on Chemical Intermediates 43, no. 12 (2017): 7211–21.
  • S. J. Saghanezhad, M. H. Sayahi, I. Imanifar, M. Mombeni, and S. Deris Hamood, “Caffeine-H3PO4: A Novel Acidic Catalyst for Various One-Pot Multicomponent Reactions,” Research on Chemical Intermediates 43, no. 11 (2017): 6521–36.
  • A. Maleki, A. R. Akbarzade, and A. R. Bhat, “Green Synthesis of Polyhydroquinolines via MCR Using Fe3O4/SiO2–OSO3H Nanostructure Catalyst and Prediction of Their Pharmacological and Biological Activities by PASS,” Journal of Nanostructure in Chemistry 7, no. 4 (2017): 309–16.
  • A. Yaghoubi, M. G. Dekamin, and B. Karimi, “Propylsulfonic Acid-Anchored Isocyanurate-Based Periodic Mesoporous Organosilica (PMO-ICS-PrSO3H): A Highly Efficient and Recoverable Nanoporous Catalyst for the One-Pot Synthesis of Substituted Polyhydroquinolines,” Catalysis Letters 147, no. 10 (2017): 2656–63.
  • Y. Chen, Z. Zhang, W. Jiang, M. Zhang, and Y. Li, “RuIII@CMC/Fe3O4 Hybrid: An Efficient, Magnetic, Retrievable, Self-Organized Nanocatalyst for Green Synthesis of Pyranopyrazole and Polyhydroquinoline Derivatives,” Molecular Diversity 23, no. 2 (2019): 421–42.
  • S. Andalibi Salem, A. Khazaei, J. Y. Seyf, N. Sarmasti, and M. Mahmoudiani Gilan, “Preparation of Magnetic Cu (II) Nano-Structure (Based on Nano-Fe3O4) and Application to the Synthesis of Hexahydroquinoline Derivatives,” Polycyclic Aromatic Compounds (2019): 1–14.
  • A. Ghorbani‐Choghamarani, Z. Heidarnezhad, B. Tahmasbi, and G. Azadi, “TEDETA@BNPs as a Basic and Metal Free Nanocatalyst for Knoevenagel Condensation and Hantzsch Reaction,” Journal of the Iranian Chemical Society 15, no. 10 (2018): 2281–93.
  • M. A. Ashraf, Z. Liu, W. X. Peng, and C. Gao, “New Copper Complex on Fe3O4 Nanoparticles as a Highly Efficient Reusable Nanocatalyst for Synthesis of Polyhydroquinolines in Water,” Catalysis Letters 150, no. 3 (2020): 683–701.
  • A. V. Borhade, B. K. Uphade, and A. G. Gadhave, “Calcinized Eggshell: An Environmentally Benign Green Catalyst for Synthesis of 2-Arylbenzothiazole Derivatives,” Research on Chemical Intermediates 42, no. 7 (2016): 6301–11.
  • A. V. Borhade, B. K. Uphade, and A. G. Gadhave, “Efficient, Solvent Free Synthesis of Acridinediones Catalysed by CdO Nanoparticles,” Research on Chemical Intermediates 41, no. 3 (2015): 1447–58.
  • G. D. Shirole, A. G. Gadhave, S. Bhalekar, and S. N. Shelke, “Acidic Ionic Liquid 1-Methyl-2-Pyrolidinium Hydrogen Sulfate: A Green Protocol for the Synthesis of 3,4-Dihydipyrimidin-2(1H)-Ones via Microwave Assisted Multi-Component Reaction,” Indian Journal of Heterocyclic Chemistry 27, no. 2 (2017): 195–201.
  • A. G. Gadhave, R. B. Gaikar, S. R. Kuchekar, and B. K. Karale, “Synthesis and Antimicrobial Activity of Some Novel [4-(1,2,3-Thiadiazol-4-yl) Phenoxy] Methylene Anchored 1,3,4-Triazoles and 1,3,4-Thiadiazoles,” Journal of Heterocyclic Chemistry 51, no. 6 (2014): 1849–55.
  • R. L. Siqueira, I. V. P. Yoshida, L. C. Pardini, and M. A. Schiavon, “Poly (Borosiloxanes) as Precursors for Carbon Fiber Ceramic Matrix Composites,” Materials Research 10, no. 2 (2007): 147–51.
  • J. S. Yeo, T. H. Park, M. H. Seo, J. Miyawaki, I. Mochida, and S. H. Yoon, “Enhancement of the Rate Capability of Graphite via the Introduction of Boron–Oxygen Functional Groups,” International Journal of Electrochemical Science 8 (2013): 1308–15.
  • A. Khalafi-Nezhad, H. O. Foroughi, M. M. Doroodmand, and F. Panahi, “Silica Boron–Sulfuric Acid Nanoparticles (SBSANs): Preparation, Characterization and Their Catalytic Application in “Ritter Reaction” for Synthesis of Amide Derivatives,” Journal of Materials Chemistry 21, no. 34 (2011): 12842–51.
  • H. J. Jung, Y. K. Sohn, H. G. Sung, H. S. Hyun, and W. G. Shin, “Physicochemical Properties of Ball Milled Boron Particles: Dry vs. Wet Ball Milling Process,” Powder Technology 269 (2015): 548–53.
  • C. Mandilas, E. Daskalos, G. Karagiannakis, and A. G. Konstandopoulos, “Synthesis of Aluminium Nanoparticles by Arc Plasma Spray under Atmospheric Pressure,” Materials Science and Engineering B 178, no. 1 (2013): 22–30.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.