Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 52, 2022 - Issue 21
325
Views
2
CrossRef citations to date
0
Altmetric
Articles

β-cyclodextrin: Green catalyst for the efficient and expeditious synthesis of benzodiazepines under aqueous conditions

, , , &
Pages 2057-2066 | Received 25 Apr 2022, Published online: 07 Oct 2022

References

  • Rotstein, B. H.; Zaretsky, S.; Rai, V.; Yudin, A. K. Small Heterocycles in Multicomponent Reactions. Chem. Rev. 2014, 114, 8323–8359. DOI: 10.1021/cr400615v.
  • Mali, A. S.; Potnis, C. S.; Chaturbhuj, G. U. 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. J. Iran. Chem. Soc. 2018, 15, 1399–1409. DOI: 10.1007/s13738-018-1340-0.
  • Gadkari, Y. U.; Hatvate, N. T.; Telvekar, V. N. Concentrated Solar Radiation-Assisted One-Pot/Multicomponent Synthesis of Pyranopyrazole Derivatives under Neat Condition. Res. Chem. Intermed. 2021, 47, 4245–4255. DOI: 10.1007/s11164-021-04530-7.
  • Barkule, A. B.; Gadkari, Y. U.; Telvekar, V. N. One-Pot Multicomponent Synthesis of 3-Methyl-4-(Hetero)Arylmethylene Isoxazole-5(4H)-Ones Using Guanidine Hydrochloride as the Catalyst under Aqueous Conditions. Polycycl. Aromat. Compd. 2021, 1–12. DOI: 10.1080/10406638.2021.1959353.
  • Khatri, C. K.; Rekunge, D. S.; Chaturbhuj, G. U. Sulfated Polyborate: A New and Eco-Friendly Catalyst for One-Pot Multi-Component Synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones/Thiones via Biginelli Reaction. New J. Chem. 2016, 40, 10412–10417. DOI: 10.1039/C6NJ03120J.
  • Gadkari, Y. U.; Jadhav, N. L.; Hatvate, N. T.; Telvekar, V. N. Concentrated Solar Radiation Aided Green Approach for Preparative Scale and Solvent‐Free Synthesis of 3‐Methyl‐4‐(Hetero)Arylmethylene Isoxazole‐5(4H)‐Ones. ChemistrySelect 2020, 5, 12320–12323. DOI: 10.1002/slct.202003348.
  • Buffett-Jerrott, S.; Stewart, S. Cognitive and Sedative Effects of Benzodiazepine Use. CPD 2002, 8, 45–58. DOI: 10.2174/1381612023396654.
  • Riss, J.; Cloyd, J.; Gates, J.; Collins, S. Benzodiazepines in Epilepsy: Pharmacology and Pharmacokinetics. Acta Neurol. Scand. 2008, 118, 69–86. DOI: 10.1111/j.1600-0404.2008.01004.x.
  • Swartz, M.; Landerman, R.; George, L. K.; Melville, M. L.; Blazer, D.; Smith, K. Benzodiazepine anti-Anxiety Agents: Prevalence and Correlates of Use in a Southern Community. Am. J. Public Health 1991, 81, 592–596. DOI: 10.2105/AJPH.81.5.592.
  • Vandyck, K.; Cummings, M. D.; Nyanguile, O.; Boutton, C. W.; Vendeville, S.; McGowan, D.; Devogelaere, B.; Amssoms, K.; Last, S.; Rombauts, K.; et al. Structure-Based Design of a Benzodiazepine Scaffold Yields a Potent Allosteric Inhibitor of Hepatitis C NS5B RNA Polymerase. J. Med. Chem. 2009, 52, 4099–4102. DOI: 10.1021/jm9005548.
  • Michelini, S.; Cassano, G.; Frare, F.; Perugi, G. Long-Term Use of Benzodiazepines: Tolerance, Dependence and Clinical Problems in Anxiety and Mood Disorders. Pharmacopsychiatry 2007, 29, 127–134. DOI: 10.1055/s-2007-979558.
  • De, S. K.; Gibbs, R. A. Scandium(III) Triflate as an Efficient and Reusable Catalyst for Synthesis of 1,5-Benzodiazepine Derivatives. Tetrahedron Lett. 2005, 46, 1811–1813. DOI: 10.1016/j.tetlet.2005.01.113.
  • Beccalli, E. M.; Broggini, G.; Paladino, G.; Penoni, A.; Zoni, C. Regioselective Formation of Six- and Seven-Membered Ring by Intramolecular Pd-Catalyzed Amination of N-Allyl-Anthranilamides. J. Org. Chem. 2004, 69, 5627–5630. DOI: 10.1021/jo0495135.
  • Karimi-Jaberi, Z.; Hooshmandpour, A. One-Pot Synthesis of 4-Substituted-1,5-Benzodiazepines Promoted by Tris(Hydrogensulfato) Boron. Polycycl. Aromat. Compd. 2020, 40, 432–436. DOI: 10.1080/10406638.2018.1441876.
  • Schimer, J.; Cígler, P.; Veselý, J.; Grantz Šašková, K.; Lepšík, M.; Brynda, J.; Rezáčová, P.; Kožíšek, M.; Císařová, I.; Oberwinkler, H.; et al. Structure-Aided Design of Novel Inhibitors of HIV Protease Based on a Benzodiazepine Scaffold. J. Med. Chem. 2012, 55, 10130–10135. DOI: 10.1021/jm301249q.
  • Nagaraju, S.; Perumal P, O.; Divakar, K.; Paplal, B.; Kashinath, D. On Water” Synthesis of Dibenzo-[1,4]-Diazepin-1-Ones Using l-Proline as an Organocatalyst and under Catalyst-Free Conditions, and Their Evaluation as α-Glucosidase Inhibitors. New J. Chem. 2017, 41, 8993–9001. DOI: 10.1039/C7NJ01021D.
  • Naeimi, H.; Foroughi, H. Facile Three-Component Preparation of Benzodiazepine Derivatives Catalyzed by Zinc Sulfide Nanoparticles via Grinding Method. Res. Chem. Intermed. 2016, 42, 3999–4020. DOI: 10.1007/s11164-015-2254-4.
  • Hazai, V.; Szabó, T.; Volk, B.; Milen, M. Propylphosphonic Anhydride (T3P®)-Mediated Three-Component Synthesis of Hexahydrodibenzo. Chem. Heterocycl. Compd. 2020, 56, 237–240. DOI: 10.1007/s10593-020-02650-3.
  • Zhu, X.-T.; Liu, J.-Y.; Jiang, B.; Tu, S.-J. Microwave-Assisted Aqueous Reactions: An Efficient Route to Benzodiazepines: Microwave-Assisted Aqueous Reactions: An Efficient Route to Benzodiazepines. J. Heterocycl. Chem. 2015, 52, 92–96. DOI: 10.1002/jhet.1988.
  • Nongrum, R.; Kharmawlong, G. K.; Rani, J. W. S.; Rahman, N.; Dutta, A.; Nongkhlaw, R. Organocatalytic Green Approach towards the Fabrication of Fused Benzo N,N‐Containing Heterocycles Facilitated by Ultrasonic Irradiation. J. Heterocycl. Chem. 2019, 56, 2873–2883. DOI: 10.1002/jhet.3680.
  • Shoeb, M.; Mobin, M.; Ali, A.; Zaman, S.; Naqvi, A. H. Graphene-Mesoporous Anatase TiO2 Nanocomposite: A Highly Efficient and Recyclable Heterogeneous Catalyst for One-Pot Multicomponent Synthesis of Benzodiazepine Derivatives. Appl. Organomet. Chem. 2018, 32, e3961. DOI: 10.1002/aoc.3961.
  • Villalonga, R.; Cao, R.; Fragoso, A. Supramolecular Chemistry of Cyclodextrins in Enzyme Technology. Chem. Rev. 2007, 107, 3088–3116. DOI: 10.1021/cr050253g.
  • Szejtli, J. Introduction and General Overview of Cyclodextrin Chemistry. Chem. Rev. 1998, 98, 1743–1754. DOI: 10.1021/cr970022c.
  • Breslow, R.; Dong, S. D. Biomimetic Reactions Catalyzed by Cyclodextrins and Their Derivatives. Chem. Rev. 1998, 98, 1997–2012. DOI: 10.1021/cr970011j.
  • Desper, J. M.; Breslow, R. Catalysis of an Intramolecular Aldol Condensation by Imidazole-Bearing Cyclodextrins. J. Am. Chem. Soc. 1994, 26, 12081–12082.
  • Takahashi, K. Organic Reactions Mediated by Cyclodextrins. Chem. Rev. 1998, 98, 2013–2034. DOI: 10.1021/cr9700235.
  • Chate, A. V.; Kulkarni, A. S.; Jadhav, C. K.; Nipte, A. S.; Bondle, G. M. Multicomponent Reactions and Supramolecular Catalyst: A Perfect Synergy for Eco‐Compatible Synthesis of Pyrido [2,3‐d] Pyrimidines in Water. J. Heterocycl. Chem. 2020, 57, 2184–2193. DOI: 10.1002/jhet.3938.
  • Tungala, K.; Adhikary, P.; Azmeera, V.; Kumar, K.; Krishnamoorthi, S. Dendritic Star Polymer of Polyacrylamide Based on a β-Cyclodextrin Trimer: A Flocculant and Drug Vehicle. New J. Chem. 2017, 41, 611–618. DOI: 10.1039/C6NJ02599D.
  • Jadhav, C. K.; Nipate, A. S.; Chate, A. V.; Songire, V. D.; Patil, A. P.; Gill, C. H. Efficient Rapid Access to Biginelli for the Multicomponent Synthesis of 1,2,3,4-Tetrahydropyrimidines in Room-Temperature Diisopropyl Ethyl Ammonium Acetate. ACS Omega 2019, 4, 22313–22324. DOI: 10.1021/acsomega.9b02286.
  • Nipate, A. S.; Jadhav, C. K.; Chate, A. V.; Taur, K. S.; Gill, C. H. 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. J. Heterocycl. Chem. 2020, 57, 820–829. DOI: 10.1002/jhet.3828.
  • Chate, A. V.; Dongre, R. M.; Khaire, M. K.; Bondle, G. M.; Sangshetti, J. N.; Damale, M. β-CD-Catalyzed Multicomponent Domino Reaction: Synthesis, Characterization, In Silico Molecular Docking and Biological Evaluation of Pyrano[2,3-d]-Pyrimidinone Derivatives. Res. Chem. Intermed 2018, 44, 6119–6136. DOI: 10.1007/s11164-018-3479-9.
  • Savari, A.; Heidarizadeh, F.; Pourreza, N. Synthesis and Characterization of CoFe2O4@SiO2@NH-NH2-PCuW as an Acidic Nano Catalyst for the Synthesis of 1,4-Benzodiazepines and a Powerful Dye Remover. Polyhedron 2019, 166, 233–247. DOI: 10.1016/j.poly.2019.03.046.
  • Mozafari, R.; Ghadermazi, M. A Nickel Nanoparticle Engineered CoFe2O4@GO–Kryptofix 22 Composite: A Green and Retrievable Catalytic System for the Synthesis of 1,4-Benzodiazepines in Water. RSC Adv. 2020, 10, 15052–15064. DOI: 10.1039/D0RA01671C.
  • Kausar, N.; Mukherjee, P.; Das, A. R. Practical Carbocatalysis by Graphene Oxide Nanosheets in Aqueous Medium towards the Synthesis of Diversified Dibenzo[1,4]Diazepine Scaffolds. RSC Adv. 2016, 6, 88904–88910. DOI: 10.1039/C6RA17520A.
  • Tarannum, S.; Siddiqui, Z. N. Fe(OTs)3/SiO2: A Novel Catalyst for the Multicomponent Synthesis of Dibenzodiazepines under Solvent-Free Conditions. RSC Adv. 2015, 5, 74242–74250. DOI: 10.1039/C5RA12085C.
  • Brahmbhatt, G. C.; Sutariya, T. R.; Atara, H. D.; Parmar, N. J.; Gupta, V. K.; Lagunes, I.; Padrón, J. M.; Murumkar, P. R.; Yadav, M. R. Diazepinones: Room Temperature One-Pot Synthesis and Biological Evaluation. Mol. Divers. 2020, 24, 355–377.
  • Hanze, A. R.; Strube, R. E.; Greig, M. E. Dibenzo[b,e][1,4]Diazepines. J. Med. Chem. 1963, 6, 767–771.

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.