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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 5
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Articles

Facile synthesis of 1-(arylimino)naphthalen-2(1H)-ones from anilines and 2-naphthols promoted by NaBr/K2S2O8/CAN

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Pages 704-714 | Received 28 Sep 2018, Published online: 07 Feb 2019

References

  • Fox, M. A.; Whitesell, J. K. Organic Chemistry; Jones & Bartlett: Boston, 2nd edn., 1997, ch. 11, p. 577.
  • Wang, P.; Gao, Y.; Zhao, Y.; Liu, W.; Wang, Y. Unveiling Mechanism of a Quinine-Squaramide Catalyzed Enantioselective Aza-Friedel-Crafts Reaction between Cyclic Trifluoromethyl Ketimine and Naphthol: A DFT Study. J. Org. Chem. 2017, 82, 13109-13114. DOI: 10.1021/acs.joc.7b02168.
  • Shao, L.; Wang, Y.-H.; Zhang, D.-Y.; Xu, J.; Hu, X.-P. Desilylation-Activated Propargylic Transformation: Enantioselective Copper-Catalyzed [3 + 2] Cycloaddition of Propargylic Esters with β-Naphthol or Phenol Derivatives. Angew. Chem. Int. Ed. 2016, 55, 5014-5018. DOI: 10.1002/anie.201510793.
  • Zolfigol, M. A.; Navazeni, M.; Yarie, M.; Ayazi-Nasrabadi, R. Catalytic Application of [Fe3O4@SiO2@(CH2)3-Urea-SO3H/HCl] as a Magnetically Recoverable Solid Acid at the Synthesis of 2′-aminobenzothiazolomethylnaphthols. Res. Chem. Intermed. 2018, 44, 191-200. DOI: 10.1007/s11164-017-3097-y.
  • Frederickson, C. K.; Rose, B. D.; Haley, M. M. Explorations of the Indenofluorenes and Expanded Quinoidal Analogues. Acc. Chem. Res. 2017, 50, 977-987. DOI: 10.1021/acs.accounts.7b00004.
  • Zhang, Z.-B.; Sun, Q.-S.; Xu, D.-Q.; Xia, C.-G.; Sun, W. Direct Halogenative Dearomatization of 2-Naphthols by NXS (X = Cl, Br) in Water. Green Chem. 2016, 18, 5485–5492. DOI: 10.1039/c6gc01673a.
  • Ge, C.-Z.; Yang, H.-X.; Miyawaki, J.; Mochida, I.; Yoon, S. H.; Qiao, W.-M.; Long, D.-H.; Ling, L. Synthesis and Characterization of High-Softening-Point Methylene-Bridged Pitches by Visible Light Irradiation Assisted Free-radical Bromination. C. Carbon 2015, 95, 780-788. DOI: 10.1016/j.carbon.2015.09.003.
  • Wang, R.-R.; Shi, K.; Cai, K.; Guo, Y.-K.; Yang, X.; Wang, J.-Y.; Pei, J.; Zhao, D.-H. Syntheses of Polycyclic Aromatic Diimides via Intramolecular Cyclization of Maleic Acid Derivatives. New J. Chem. 2016, 40, 113-121. DOI: 10.1039/C5NJ01849H.
  • Jiang, W.; Li, Y.; Wang, Z.-H. Tailor-made Rylene Arrays for High Performance n-channel Semiconductors. Acc. Chem. Res. 2014, 47, 3135-3147. DOI: 10.1021/ar500240e.
  • Karmaker, P. G.; Qiu, J.-S.; Wu, D.; Yin, H.-Q.; Chen, F.-X. Free Radical Cyclization of N-Arylacrylamides: Mild and Facile Synthesis of 3-Thiocyanato Oxindoles. Synlett 2018, 29, 954-958. DOI: 10.1055/s-0036-1591927.
  • Saikia, I.; Borah, A. J.; Phukan, P. Use of Bromine and Bromo-Organic Compounds in Organic Synthesis. Chem. Rev. 2016, 116, 6837-7042. DOI: 10.1021/acs.chemrev.5b00400.
  • Xie, J.-N.; Diao, Z.-F.; Qiao, C.; Ma, R.; He, L.-N. One-Pot Stepwise Synthesis of Cyclic Carbonates Directly from Olefins with CO2 Promoted by K2S2O8/NaBr. J. CO2 Util 2016, 16, 313-317. DOI: 10.1016/j.jcou.2016.08.009.
  • Natarajan, P. Facile Synthesis of Symmetric Thiosulfonates by Oxidation of Disulfide with Oxone/MX (MX = KBr, KCl, NaBr and NaCl). Tetrahedron Lett. 2015, 56, 4131-4134. DOI: 10.1016/j.tetlet.2015.05.050.
  • Babu, S. S.; Shanmugam, S. CAN-Supported Chemoselective Oxidative Conversion of a-Aroylketene-(S,S)-acetals to Aryl Carboxylic Acids. Chem. Select. 2017, 2, 2330-2334. DOI: 10.1002/slct.201700107.
  • Zolfigol, M. A.; Amani, K.; Hajjami, M.; Choghamarani, A. G. Selective and Efficient Oxidation of Sulfides to Sulfoxides Using Ammonium Cerium (IV) Nitrate in the Presence of a Catalytic Amount of KBr or NaBr. Monatsh. Chem. 2008, 139, 895-899. DOI: 10.1007/s00706-008-0868-6.
  • Ali, M. H.; Leach, D. R.; Schmitz, C. E. A Simple and Efficient Procedure for Oxidation of Sulfides to Sulfoxides on Hydrated Silica Gel with Ceric Ammonium Nitrate (Can) In Methylene Chloride. Synth. Commun. 1998, 28, 2969-2981. DOI: 10.1080/00397919808004876.
  • Prajapati, N. P.; Vekariya, R. H.; Patel, H. D. Ceric Ammonium Nitrate (CAN)–Catalyzed Multicomponent Reactions: An Efficient Catalyst for Green Organic Synthesis. Synth. Commun. 2015, 44, 2399-2425. DOI: 10.1080/00397911.2015.1045986.
  • Pegu, C. D.; Nasrin, S. B.; Deb, M. L.; Das, D. J.; Saikia, K. K.; Baruah, P. K. CAN-catalyzed Microwave Promoted Reaction of Indole with Betti Bases under Solvent-Free Condition and Evaluation of Antibacterial Activity of the Products. Synth. Commun. 2017, 47, 2007-2014. DOI: 10.1080/00397911.2017.1360912.
  • Alaoui, S.; Driowya, M.; Demange, L.; Benhida, R.; Bougrin, K. Ultrasound-Assisted Facile One-Pot Sequential Synthesis of Novel Sulfonamide-Isoxazoles Using Cerium (IV) Ammonium Nitrate (CAN) as an Efficient Oxidant in Aqueous Medium. Ultrason. Sonochem. 2018, 40, 289-297. DOI: 10.1016/j.ultsonch.2017.07.019.
  • Cao, Z.-Y.; Zhou, F.; Zhou, J. Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles. Acc. Chem. Res. 2018, 51, 1443-1454. DOI: 10.1021/acs.accounts.8b00097.
  • Hajra, S.; Bhosale, S. S.; Hazra, A. An Asymmetric Acetate-Mannich Reaction of Chiral Isatin Derived Ketimines and Its Applications. Org. Biomol. Chem. 2017, 15, 9217-9225. DOI: 10.1039/C7OB02407J.
  • Liu, Y.; Liu, Y.; Wang, J.; Wei, Z.; Cao, J.; Liang, D.; Lin, Y.; Duan, H. Asymmetric Phase-Transfer Catalysts Bearing Multiple Hydrogen-Bonding Donors: Synthesis and Application in Nitro-Mannich Reaction of Isatin-Derived N-Boc Ketimines. Tetrahedron Lett. 2017, 58, 2400-2403. DOI: 10.1016/j.tetlet.2017.05.022.
  • Soliman, F. M.; Said, M. M.; Maigali, S. S. Chemistry of Phosphorus Ylides 21 New Route for the Synthesis of Azetidinones. Reaction of Phosphonium Ylides with Benzil-,o-naphthoquinone-, and Triketonemonoanils. Heteroatom Chem. 2005, 16, 476-483. DOI: 10.1002/hc.20144.
  • Hamrouni, K.; Batanero, B.; Barba, F.; Barba, I.; Boujlel, K.; Benkhoud, M. L. C. Reduction of 1,2-dicarbonyl Compounds and of Their N-phenylimine Derivatives by Sodium Cyanide under Aprotic Conditions. R. Chimie. 2015, 18, 1284-1288. DOI: 10.1016/j.crci.2015.07.007.
  • Bamford, K. L.; Longobardi, L. E.; Liu, L.; Grimme, S.; Stephan, D. W. FLP Reduction and Hydroboration of Phenanthrene o-iminoquinones and α-Diimines. Dalton Trans. 2017, 46, 5308-5319. DOI: 10.1039/C7DT01024A.

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