Aqueous Media Synthesis of Pyrano[3,2-c]chromen Derivatives Using Magnesium Oxide Nanoparticles as a Recyclable Catalyst

References

• H. Gourdeau, L. Leblond, B. Hamelin, C. Desputeau, K. Dong, I. Kianicka, D. Custeau, C. Boudreau, L. Geerts, S.-X. Cai, et al. “Antivascular and Antitumor Evaluation of 2-amino-4-(3- bromo-4,5-dimethoxy-phenyl)-3-cyano-4H-chromenes, a Novel Series of Anticancer Agents,” Molecular Cancer Therapeutics 3 (2004): 1375–84.
   PubMed Web of Science ®Google Scholar
• B. S. Chetan, M. S. Nimesh, P. P. Manish, and G. P. Ranjan, “Microwave Assisted Synthesis of Novel 4H-chromene Derivatives Bearing Phenoxypyrazole and Their Antimicrobial Activity Assess,”Journal of the Serbian Chemical Society 77 (2012): 1–17.
   Web of Science ®Google Scholar
• A. Burgard, H. J. Lang, and U. Gerlach, “Asymmetric Synthesis of 4-amino-3, 4 - dihydro-2, 2-dimethyl-2H-1- Benzopyrans,” Tetrahedron 55, no. 24 (1999): 7555–62.
   Web of Science ®Google Scholar
• J. M. Evans, C. S. Fake, T. C. Hamilton, R. H. Poyser, and G. A. Showell, “Synthesis and Antihypertensive Activity of 6,7-disubstituted Trans-4-amino- 3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-Ols,” Journal of Medicinal Chemistry 27, no. 9 (1984): 1127–31.
   PubMed Web of Science ®Google Scholar
• R.-R. Zhang, J. Liu, Y. Zhang, M.-Q. Hou, M.-Z. Zhang, F. Zhou, and W.-H. Zhang, “Microwave-assisted Synthesis and Antifungal Activity of Novel Coumarin Derivatives: Pyrano[3,2-c]chromene-2,5-Diones,” European Journal of Medicinal Chemistry 116 (2016): 76–83.
   PubMed Web of Science ®Google Scholar
• D. C. Mungra, M. P. Patel, D. P. Rajani, and R. G. Patel, “Synthesis and Identification of β-Aryloxyquinolines and Their Pyrano[3,2-c]chromene Derivatives as a New Class of Antimicrobial and Antituberculosis Agents,” European Journal of Medicinal Chemistry 46, no. 9 (2011): 4192–200.
   PubMed Web of Science ®Google Scholar
• L. Bonsignore, G. Loy, D. Secci, and A. Calignano, “Synthesis and Pharmacological Activity of 2-oxo-(2H) 1-Benzopyran-3-carboxamide Derivatives,” European Journal of Medicinal Chemistry 28, no. 6 (1993): 517–20.
   Web of Science ®Google Scholar
• A. R. Saundane, K. Vijaykumar, and A. V. Vaijinath, “Synthesis of Novel 2-Amino- 4-(5'-substituted2'-phenyl-1H-indol-3'-yl)-6-aryl-4H-pyran-3-carbonitrile Derivatives as Antimicrobial and Antioxidant Agents,” Bioorganic and Medicinal Chemistry Letters 23, no. 7 (2013): 1978–84.
   PubMed Web of Science ®Google Scholar
• J. A. Makawana, M. P. Patel, and R. G. Patel, “Synthesis and Antimicrobial Evaluation of New Pyrano [4, 3 - b] pyran and Pyrano [3, 2 - c] chromene Derivatives Bearing 2-thiophenoxy Quinoline Nucleus,” Archiv Der Pharmazie 345, no. 4 (2012): 314–22.
   PubMed Web of Science ®Google Scholar
• A. Venkatesham, R. S. Rao, K. Nagaiah, J. S. Yadav, G. R. Jones, S. J. Basha, B. Sridhar, and A. Addlagatta, “Synthesis of New Chromeno-annulated Cisfused Pyrano [3, 4-c] pyran Derivatives via Domino Knoevenagel-hetero-dielsalder Reactions and Their Biological Evaluation towards Antiproliferative Activity,” MedChemComm 3, no. 6 (2012): 652–8.
   Web of Science ®Google Scholar
• N. Jagadishbabu and K. Shivashankar, “Pseudo Multicomponent Reaction: Synthesis of Fused Pyrano Biscoumarin Analogs from 1,2‐Diols,” Journal of Heterocyclic Chemistry 54, no. 2 (2017): 1543–9.
   Web of Science ®Google Scholar
• K. Shivashankar, M. V. Kulkarni, L. A. Shastri, V. P. Rasal, and S. V. Rajendra, “The Synthesis and Biological Evaluation of Regioisomeric Benzothiazolyl Coumarins,” Phosphorus, Sulfur, and Silicon and the Related Elements 181, no. 9 (2006): 2187–200.
   Web of Science ®Google Scholar
• K. Shivashankar, L. A. Shastri, M. V. Kulkarni, V. P. Rasal, and S. V. Rajendra, “Synthetic and Biological Studies on 4-Aryloxymethyl Coumarinyl Thiazolidinones,” Phosphorus, Sulfur, and Silicon and the Related Elements 183, no. 1 (2007): 56–68.
   Web of Science ®Google Scholar
• M. M. Heravi, B. Alimadadi Jani, F. Derikvand, F. F. Bamoharram, and H. A. Oskooie, “Three Component, One-pot Synthesis of Dihydropyrano[3,2-c]chromene Derivatives in the Presence of H6P2W18O62•18H2O as a Green and Recyclable Catalyst,” Catalysis Communications 10, no. 3 (2008): 272–5.
   Web of Science ®Google Scholar
• J. M. Khurana, B. Nand, and P. Saluja, “DBU: a Highly Efficient Catalyst for One-pot Synthesis of Substituted 3,4-Dihydropyrano[3,2-c]chromenes, Dihydropyrano[4,3-b]pyranes, 2-Amino-4H-benzo[h]chromenes and 2-Amino-4Hbenzo[g]chromenes in Aqueous Medium,” Tetrahedron 66, no. 30 (2010): 5637–41.
   Web of Science ®Google Scholar
• M. Ghashang, S. S. Mansoor, and K. Aswin, “Thiourea Dioxide: An Efficient and Reusable Organocatalyst for the Rapid One-pot Synthesis of Pyrano [4, 3-b] pyran Derivatives in Water,” Chinese Journal of Catalysis 35, no. 1 (2014): 127–33.
   Web of Science ®Google Scholar
• M. Ghashang, M. Kargar, M. R. M. Shafiee, S. S. Mansoor, A. Fazlinia, and H. Esfandiari, “CuO Nano-structures Prepared in Rosmarinus Officinalis Leaves Extract Medium: Efficient Catalysts for the Aqueous Media Preparation of Dihydropyrano [3, 2-c] Chromene Derivatives,” Recent Patents on Nanotechnology 9, no. 3 (2015): 204–11.
   PubMed Web of Science ®Google Scholar
• A. Baziar and M. Ghashang, “Preparation of Pyrano [3, 2-c] Chromene-3-carbonitriles Using ZnO Nano-particles: A Comparison between the Box–Behnken Experimental Design and Traditional Optimization Methods,” Reaction Kinetics, Mechanisms and Catalysis 118, no. 2 (2016): 463–79.
   Web of Science ®Google Scholar
• M. Ghashang, “Bi2O3 Nano-particles as an Efficient Catalyst for the Multi-component, One-pot, Aqueous Media Preparation of Benzo[h]pyrano[3,2-c]chromene-2-carbonitriles and Pyrano[3,2-g]chromene-7-Carbonitriles,” Biointerface Research in Applied Chemistry 6 (2016): 1338–44.
   Web of Science ®Google Scholar
• M. Ghashang, “ZnAl2O4–Bi2O3 Composite Nano-powder as an Efficient Catalyst for the Multi-component, One-pot, Aqueous Media Preparation of Novel 4H-chromene-3-Carbonitriles,” Research on Chemical Intermediates 42, no. 5 (2016): 4191–205.
   Web of Science ®Google Scholar
• M. Ghashang, S. S. Mansoor, L. Shams Solaree, and A. Sharifian-Esfahani, “Multi-component, one-pot Aqueous Media Preparation of Dihydropyrano[3, 2-c]chromene Derivatives over MgO Nanoplates as an Efficient Catalyst,” Iranian Journal of Catalysis 6 (2016): 237–43.
   Web of Science ®Google Scholar
• M. Ghashang, S. S. Mansoor, M. R. Mohammad Shafiee, M. Kargar, M. Najafi Biregan, F. Azimi, and H. Taghrir, “Green Chemistry Preparation of MgO Nanopowders: Efficient Catalyst for the Synthesis of Thiochromeno [4, 3-b] pyran and Thiopyrano [4, 3-b] pyran Derivatives,” Journal of Sulfur Chemistry 37, no. 4 (2016): 377–90.
   Web of Science ®Google Scholar
• M. S. Singh, G. C. Nandi, and S. Samai, “DABCO-Promoted Three-component Regioselective Synthesis of Functionalized Chromen-5-ones and Pyrano[3,2-c]chromen-5-ones via Direct Annulation of α-oxoketene-N,S-arylaminoacetals Under Solvent-free Conditions,” Green Chemistry 14, no. 2 (2012): 447–55.
   Web of Science ®Google Scholar
• K. Pradhan, S. Paula, and A. R. Das, “Magnetically Retrievable Nano Crystalline CuFe2O4 Catalyzed Multi-component Reaction: A Facile and Efficient Synthesis of Functionalized Dihydropyrano[2,3-c]pyrazole, Pyrano[3,2-c]coumarin and 4H-chromene Derivatives in Aqueous Media,” Catalysis Science & Technology 4 (2014): 822–31.
   Web of Science ®Google Scholar
• H.-J. Wang, J. Lu, and Z.-H. Zhang, “Highly Efficient Three-component, One-pot Synthesis of Dihydropyrano[3,2-c]chromene Derivatives,” Monatshefte Für Chemie - Chemical Monthly 141, no. 10 (2010): 1107–12.
   Google Scholar
• N. D. Vala, H. H. Jardosh, and M. P. Patel, “PS-TBD Triggered General Protocol for the Synthesis of 4H-chromene, Pyrano[4,3-b]pyran and Pyrano[3,2-c]chromene Derivatives of 1H-pyrazole and Their Biological Activities,” Chinese Chemical Letters 27, no. 1 (2016): 168–72.
   Web of Science ®Google Scholar
• S. S. Mansoor, K. Logaiya, K. Aswin, and P. N. Sudhan, “An Appropriate One-pot Synthesis of 3,4-Dihydropyrano[c]chromenes and 6-Amino-5-cyano-4-aryl-2-methyl-4H-pyrans with Thiourea Dioxide as an Efficient, Reusable Organic Catalyst in Aqueous Medium,” Journal of Taibah University for Science 9, no. 2 (2015): 213–26.
   Web of Science ®Google Scholar
• G. Brahmachari and B. Banerjee, “Facile and One-pot Access to Diverse and Densely Functionalized 2-Amino-3-cyano-4H-pyrans and Pyran-Annulated Heterocyclic Scaffolds via an Eco-Friendly Multicomponent Reaction at Room Temperature Using Urea as a Novel Organo-Catalyst,” ACS Sustainable Chemistry & Engineering 2 (2014): 411–22.
   Web of Science ®Google Scholar
• R. J. Cremlyn, An Introduction to Organosulfur Chemistry (Wiley: Chichester, 1996).
   Google Scholar
• M. Dehbashi, M. Aliahmad, M. R. Mohammad Shafiee, and M. Ghashang, “Nickel-doped SnO2 Nanoparticles: Preparation and Evaluation of Their Catalytic Activity in the Synthesis of 1-amido Alkyl-2-Naphtholes,” Inorganic and Nano-Metal Chemistry 43 (2013): 1301–6.
   Web of Science ®Google Scholar
• M. Ghashang, “Preparation and Application of Barium Sulfate Nano-particles in the Synthesis of 2, 4, 5-triaryl and N-aryl (alkyl)-2, 4, 5-triaryl Imidazoles,” Current Organic Synthesis 9, no. 5 (2012): 727–32.
   Web of Science ®Google Scholar
• M. M. R. Shafiee, M. Ghashang, and A. Fazlinia, “Preparation of 1, 4-Dihydropyridine Derivatives Using Perchloric Acid Adsorbed on Magnetic Fe3O4 Nanoparticles Coated with Silica,” Current Nanoscience 9 (2013): 197–201.
   Web of Science ®Google Scholar
• H. Taghrir, M. Ghashang, and M. N. Biregan, “Preparation of 1-Amidoalkyl-2-naphthol Derivatives Using Barium Phosphate Nano-Powders,” Chinese Chemical Letters 27, no. 1 (2016): 119–26.
   Web of Science ®Google Scholar
• M. Ghashang, S. Jabbarzare, H. Tavakoli, H. Banisadeghi, A. H. Sokhanvar, M. Lotfi, and A. Chami, “Growth of the Nano-islands of Barium Aluminum Oxide Nano-spheres on the Surface of Al2O3-MgO Composite: Preparation and Evaluation of Their Catalytic Activity,” Current Nanoscience 11, no. 1 (2015): 95–100.
   Web of Science ®Google Scholar
• M. R. Mohammad Shafiee, M. Kargar, M. S. Hashemi, and M. Ghashang, “Green Synthesis of NiFe2O4/Fe2O3/CeO2 Nanocomposite in a Walnut Green Hulls Extract Medium: Magnetic Properties and Characterization,” Current Nanoscience 12 (2016): 645–9.
   Web of Science ®Google Scholar
• A. Behmaneshfar, M. Ghashang, M. R. Mohammad Shafiee, A. Saffar-Teluri, A. Fazlinia, and H. Esfandiari, “Optimization of the Preparation Condition of 2,4,5-triphenyl-1H-imidazole over BaSO4 Nanoparticles as Catalyst Using a Response Surface Methodology (RSM),” Current Nanoscience 11, no. 1 (2015): 56–63.
   Web of Science ®Google Scholar
• M. Ghashang, H. Taghrir, M. N. Biregan, N. Heydari, and F. Azimi, “Preparation of Novel 2-(2-oxo-2 H-chromen-4-yl)-3-arylthiazolidin-4-one Derivatives Using an Efficient Ionic Liquid Catalyst,” Journal of Sulfur Chemistry 37, no. 1 (2016): 61–9.
   Web of Science ®Google Scholar