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Original Articles

Efficient One-Pot Synthesis of Tetrahydrobenzo[b]pyrans by Ethylenediamine Diacetate-Catalyzed Multicomponent Reaction Under Solvent-Free Conditions

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Pages 39-45 | Received 09 Apr 2015, Accepted 25 Aug 2015, Published online: 11 Oct 2016

References

  • Katritzky, A. R., C. W. Rees, and E. F. V. Scriven. Comprehensive Heterocyclic Chemistry II. (Oxford: Pergamon Press, 1995).
  • Singh, K., J. Singh, and H. Singh. “A Synthetic Entry into Fused Pyran Derivatives through Carbon Transfer Reactions of 1,3-Oxazinanes and Oxazolidines with Carbon Nucleophiles.” Tetrahedron 52 (1996): 14273–80.
  • Aswin, K., S. S. Mansoor, K. Logaiya, S. P. N. Sudhan, V. S. Malik, and H. Ramadoss. “Reusable Silica-Bonded S-Sulfonic Acid Catalyst for Three-Component Synthesis of 2-Amino-5-Oxo-5,6,7,8-Tetrahydro-4H-Chromenes and 2-Amino-4H-Pyrans in Aqueous Ethanol.” Research on Chemical Intermediates 40 (2014): 2583–98.
  • Joshi, V. M., R. L. Magar, P. B. Throat, S. U. Tekale, B. R. Patil, M. P. Kale, and R. P. Pawar. “Novel One-Pot Synthesis of 4H-Chromene Derivatives Using Amino Functionalized Silica Gel Catalyst.” Chinese Chemical Letters 25 (2014): 455–8.
  • Kiyani, H. and F. Ghorbani. “Potassium Phthalimide Promoted Green Multicomponent Tandem Synthesis of 2-Amino-4Hchromenes and 6-Amino-4H-Pyran-3-Carboxylates.” Journal of Saudi Chemical Society 18 (2014): 689–701.
  • Rostamnia, S., A. Nuri, H. Xin, A. Pourjavadi, and S. H. Hosseini. “Water Dispersed Magnetic Nanoparticles (H2O-dmnps) of γ-Fe2O3 for Multicomponent Coupling Reactions: a Green, Single-Pot Technique for the Synthesis of Tetrahydro-4H-Chromenes and Hexahydroquinoline Carboxylates.” Tetrahedron Letters 54 (2013): 3344–7.
  • Khaksar, S., A. Rouhollahpour, and S. M. Talesh. “A Facile and Efficient Synthesis of 2-Amino-3-Cyano-4H-Chromenes and Tetrahydrobenzo[b]pyrans Using 2,2,2-Trifluoroethanol as a Metal-Free and Reusable Medium.” Journal of Fluorine Chemistry 141 (2012): 11–15.
  • Song, S., Z. Shan, and Y. Jin. “A Cheap Amino Alcohol Catalyzed One-Pot, Tri-Component Synthesis of Tetrahydrochromene Derivatives.” Letters in Organic Chemistry 7 (2010): 64–8.
  • Banerjee, S., A. Horn, H. Khatri, and G. Sereda. “A Green One-Pot Multicomponent Synthesis of 4H-Pyrans and Polysubstituted Aniline Derivatives of Biological, Pharmacological, and Optical Applications Using Silica Nanoparticles as Reusable Catalyst.” Tetrahedron Letters 52 (2011): 1878–81.
  • Lian, X.-Z., Y. Huang, Y.-Q. Li, and W.-J. Zheng. “A Green Synthesis of Tetrahydrobenzo[b]Pyran Derivatives through Three-Component Condensation Using N-Methylimidazole as Organocatalyst.” Monatshefte fur Chemie 139 (2008): 129–31.
  • Balalaie, S., M. Sheikh-Ahmadi, and M. Bararjanian. “Tetra-Methyl Ammonium Hydroxide: an Efficient and Versatile Catalyst for the One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives in Aqueous Media.” Catalysis Communications 8 (2007): 1724–8.
  • Katkar, S. S., M. K. Lande, B. R. Arbad, and S. T. Gaikwad. “A Recyclable and Highly Effective ZnO-Beta Zeolite as a Catalyst for One-Pot Three-Component Synthesis of Tetrahydrobenzo[b]pyrans.” Chinese Journal of Chemistry 29 (2011): 199–202.
  • Nemouchi, S., R. Boulcina, B. Carboni, and A. Debache. “Phenylboronic Acid as an Efficient and Convenient Catalyst for a Three-Component Synthesis of Tetrahydrobenzo[b]pyrans.” Comptes Rendus Chimie 15 (2012): 394–7.
  • Zhi, H., C. Lv, Q. Zhang, and J. Luo. “A New PEG-1000-Based Dicationic Ionic Liquid Exhibiting Temperature-Dependent Phase Behavior with Toluene and Its Application in One-Pot Synthesis of Benzopyrans.” Chemical Communications (2009): 2878–80.
  • Wang, Y. L., Z. Li, J. Luo, and Z. L. Liu. “One-pot Synthesis of Tetrahydrobenzo[b]pyrans Catalyzed by PEG-1000 Bridged Primary Amine Functionalized Dicationic Ionic Liquid in Water.” Journal of the Chinese Chemical Society 60 (2013): 1431–6.
  • Salvi, P. P., A. M. Mandhare, A. S. Sartape, D. K. Pawar, S. H. Han, and S. S. Kolekar. “An Efficient Protocol for Synthesis of Tetrahydrobenzo[b]pyrans Using Amino Functionalized Ionic Liquid.” Comptes Rendus Chimie 14 (2011): 878–82.
  • Shaterian, H. R., M. Arman, and F. Rigi. “Domino Knoevenagel Condensation, Michael Addition, and Cyclization Using Ionic Liquid, 2-Hydroxyethylammonium Formate, as a Recoverable Catalyst.” Journal of Molecular Liquids 158 (2011): 145–50.
  • Davoodnia, A., S. Allameh, S. Fazli, and N. Tavakoli-Hoseini. “One-Pot Synthesis of 2-Amino-3-Cyano-4-Arylsubstituted Tetrahydrobenzo[b]pyrans Catalysed by Silica Gel-Supported Polyphosphoric Acid (PPA-SiO2) as an Efficient and Reusable Catalyst.” Chemical Papers 65 (2011): 714–20.
  • Tabatabaeian, K., H. Heidari, M. Mamaghani, and N. O. Mahmoodi. “Ru(II) Complexes Bearing Tertiary Phosphine Ligands: a Novel and Efficient Homogeneous Catalyst for One-Pot Synthesis of Dihydropyrano[3,2-c]chromene and Tetrahydrobenzo[b]pyran Derivatives.” Applied Organometallic Chemistry 26 (2012): 56–61.
  • Rathod, S., B. Arbad, and M. Lande. “Preparation, Characterization, and Catalytic Application of a Nanosized Ce1MgxZr1-xO2 Solid Heterogeneous Catalyst for the Synthesis of Tetrahydrobenzo[b]pyran Derivatives.” Chinese Journal of Catalysis 31 (2010): 631–6.
  • Abdollahi-Alibeik, M. and F. Nezampour. “Synthesis of 4H-Benzo[b]pyrans in the Presence of Sulfated MCM-41 Nanoparticles as Efficient and Reusable Solid Acid Catalyst.” Reaction Kinetics, Mechanisms and Catalysis 108 (2013): 213–29.
  • Balalaie, S., M. Bararjanian, A. M. Amani, and B. Movassagh. “(S)-Proline as a Neutral and Efficient Catalyst for the One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives in Aqueous Media.” Synlett (2006): 263–6.
  • Pore, D. M., K. A. Undale, B. B. Dongare, and U. V. Desai. “Potassium Phosphate Catalyzed a Rapid Three-Component Synthesis of Tetrahydrobenzo[b]pyran at Ambient Temperature.” Catalysis Letters 132 (2009): 104–8.
  • Saini, A., S. Kumar, and J. S. Sandhu. “A New LiBr-Catalyzed, Facile and Efficient Method for the Synthesis of 14-Alkyl or Aryl-14H-dibenzo[a,j]xanthenes and Tetrahydrobenzo[b]pyrans under Solvent-Free Conventional and Microwave Heating.” Synlett (2006): 1928–32.
  • Devi, I. and P. J. Bhuyan. “Sodium Bromide Catalysed One-Pot Synthesis of Tetrahydrobenzo[b]pyrans via a Three-Component Cyclocondensation under Microwave Irradiation and Solvent Free Conditions.” Tetrahedron Letters 45 (2004): 8625–7.
  • Hekmatshoar, R., S. Majedi, and K. Bakhtiari. “Sodium Selenate Catalyzed Simple and Efficient Synthesis of Tetrahydro Benzo[b]pyran Derivatives.” Catalysis Communications 9 (2008): 307–10.
  • Bhattacharyya, P., K. Pradhan, S. Paul, and A. R. Das. “Nano Crystalline ZnO Catalyzed One Pot Multicomponent Reaction for an Easy Access of Fully Decorated 4h-Pyran Scaffolds and Its Rearrangement to 2-Pyridone Nucleus in Aqueous Media.” Tetrahedron Letters 53 (2012): 4687–91.
  • Manjulatha, K., S. Srinivas, N. Mulakayala, D. Rambabu, M. Prabhakar, K. M. Arunasree, M. Alvala, M. V. B. Rao, and M. Pal. “Ethylenediamine Diacetate (EDDA) Mediated Synthesis of Aurones under Ultrasound: Their Evaluation as Inhibitors of SIRT1.” Bioorganic & Medicinal Chemistry Letters 22 (2012): 6160–5.
  • Kolla, S. R. and Y. R. Lee. “Efficient One-Pot Synthesis Of β-Phosphono Malonates and 2-Amino-4H-Chromen-4-ylphosphonate Derivatives by Ethylenediamine Diacetate-Catalyzed Three Component Reactions.” Tetrahedron 68 (2012): 226–37.
  • Zhou, Z. and Y. Sun. “Simple, Efficient, and Green Procedure for the Knoevenagel Condensation Catalyzed by Ethylenediammonium Diacetate under Solvent-Free Conditions.” Synthetic Communications 41 (2011): 3162–8.
  • Wang, X. and Y. R. Lee. “EDDA-Catalyzed Rapid Synthetic Routes for Biologically Interesting Polycycles Bearing Citrans and Chalcones: the First Total Synthesis of Sumadain A.” Tetrahedron 65 (2009): 10125–33.
  • Lee, Y. R. and T. V. Hung. “Ethylenediamine Diacetate (EDDA)-Catalyzed One-Pot Synthesis of Tetrahydroquinolines by Domino Knoevenagel/Hetero Diels-Alder Reactions from 1,3-Dicarbonyls.” Tetrahedron 64 (2008): 7338–46.
  • Lee, Y. R., J. H. Choi, and S. H. Yoon. “Efficient and General Method for the Synthesis of Benzopyrans by Ethylenediamine Diacetate-Catalyzed Reactions of Resorcinols with α,β-Unsaturated Aldehydes. One Step Synthesis of Biologically Active (±)-Confluentin and (±)-Daurichromenic Acid.” Tetrahedron Letters 46 (2005): 7539–43.
  • Shi, D. Q., M. Zhang, Q. Y. Zhuang, S. J. Tu, and H. W. Hu. “Clean Synthesis of 2-Amino-3-Cyano-4-Aryl-7,7-Dimethyl-5-oxo-4H-5,6,7,8-Tetrahydrobenzo[b]pyran in Water.” Chinese Journal of Organic Chemistry 23 (2003): 877–9.
  • Tu, S. J., Y. Gao, C. Guo, D. Shi, and Z. H. Lu. “A Convenient Synthesis of 2-Amino-5,6,7,8-Tetrahydro-5-oxo-4-Aryl-7,7-Dimethyl-4H-Benzo-[b]-Pyran-3-Carbonitrile under Microwave Irradiation.” Synthetic Communications 32 (2002): 2137–41.

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