Convenient synthesis of linear 2H,6H-pyrano[3,2-g] chromenes from natural occurring compound; visnagin

References

• Grazul, M.; Budzisz, E. Biological Activity of Metal Ions Complexes of Chromones, Coumarins and Flavones. Coord. Chem. Rev. 2009, 253, 2588–2598. DOI: 10.1016/j.ccr.2009.06.015.
   Web of Science ®Google Scholar
• Machado, N. F. L.; Marques, M. Bioactive Chromone Derivatives—Structural Diversity. Curr. Bioact. Compd. 2010, 6, 76–89. DOI: 10.2174/157340710791184859.
   Google Scholar
• Ghate, M.; Kullkarni, M. V. Synthesis and Anti-Inflammatory Activity of 4-(5′-Acetyl-6′-Hydroxy-3'-Methyl-Benzofuran-2'-yl)Coumarin and 6-Actyl-3,7-Dimethyl-2-(Coumarin-4'-yl)Furo[3,2-g]Chromen-5-One. Indian J. Chem. Sec. B 2005, 44, 1674–1678.
   Google Scholar
• Prakash, O.; Kumar, R.; Parkash, V. Synthesis and Antifungal Activity of Some New 3-Hydroxy-2-(1-Phenyl-3-Aryl-4-Pyrazolyl)Chromones. Eur. J. Med. Chem. 2008, 43, 435–440. DOI: 10.1016/j.ejmech.2007.04.004.
   PubMed Web of Science ®Google Scholar
• Chohan, Z. H.; Rauf, A.; Naseer, M. M.; Somra, M. A.; Supuran, C. T. Antibacterial, Antifungal and Cytotoxic Properties of Some Sulfonamide-Derived Chromones. J. Enzyme Inhib. Med. Chem. 2006, 21, 173–177. DOI: 10.1080/14756360500533059.
   PubMed Web of Science ®Google Scholar
• Houghton, P. J.; Woldemariam, T. Z.; Khan, A. I.; Burke, A.; Mahmood, N. Antiviral Activity of Natural and Semi-Synthetic Chromone Alkaloids. Antiviral Res. 1994, 25, 235–244. DOI: 10.1016/0166-3542(94)90006-X.
   PubMed Web of Science ®Google Scholar
• Duan, Y-D.; Jiang, Y-Y.; Guo, F-X.; Chen, L-X.; Xu, L-L.; Zhang, W.; Liu, B. The Antitumor Activity of Naturally Occurring Chromones: A Review. Fitoterapia 2019, 135, 114–129. DOI: 10.1016/j.fitote.2019.04.012.
   PubMed Web of Science ®Google Scholar
• Sethna, S. M.; Shah, N. M. The Chemistry of Coumarine. Chem. Rev. 1945, 36, 1–62. DOI: 10.1021/cr60113a001.
   Web of Science ®Google Scholar
• Bairagi, S. H.; Salaskar, P. P.; Loke, S. D.; Surve, N. N.; Tandel, D. V.; Dusara, M. D. Medicinal Significance of Coumarins: A Review. Int. J. Pharm. Res. 2012, 4, 16–19.
   Google Scholar
• Bansal, Y.; Sethi, P.; Bansal, G. Coumarin: A Potential Nucleus for anti-Inflammatory Molecules. Med. Chem. Res. 2013, 22, 3049–3060. DOI: 10.100/s00044-012-0321-6.
   Web of Science ®Google Scholar
• Kostova, I.; Bhatia, S.; Grigorov, P.; Balkansky, S.; Parmar, V. S.; Prasad, A. K.; Saso, L. Coumarins as Antioxidants. Curr Med Chem. 2011, 18, 3929–3951. DOI: 10.2174/092986711803414395.
   PubMed Web of Science ®Google Scholar
• Shi, J.; Li, C.-J.; Yang, J.-Z.; Ma, J.; Wang, C.; Tang, J.; Li, Y.; Chen, H.; Zhang, D.-M. Hepatoprotective Coumarins and Secoiridoids from Hydrangea paniculata. Fitoterapia 2014, 96, 138–145. DOI: 10.1016/j.fitote.2014.04.015.
   PubMed Web of Science ®Google Scholar
• Hu, Y.; Chen, W.; Shen, Y.; Zhu, B.; Wang, G.-X. Synthesis and Antiviral Activity of Coumarin Derivatives against Infectious Hematopoietic Necrosis Virus. Bioorg. Med. Chem. Lett. 2019, 29, 1749–1755. DOI: 10.1016/j.bmcl.2019.05.019.
   PubMed Web of Science ®Google Scholar
• Al-Majedy, Y. K.; Kadhum, A. H.; Al-Amiery, A. A.; Mohamad, A. Coumarins: The Antimicrobial Agents. Sys. Rev. Pharm. 2017, 8, 62–70. DOI: 10.5530/srp.2017.1.11.
   Google Scholar
• Thakur, A.; Singla, R.; Jaitak, V. Coumarins as Anticancer Agents: A Review on Synthetic Strategies, Mechanism of Action and SAR Studies. Eur. J. Med. Chem. 2015, 101, 476–495. DOI: 10.1016/j.ejmech.2015.07.010.
   PubMed Web of Science ®Google Scholar
• Hishmat, O. H.; Khalil, K. M. A.; El-Naem, S. I.; Abd El-Rahman, A. H. Synthesis of Pyranobenzopyranopyridines and Benzodipyran Derivatives. Z. Naturforsch. B Chem. Sci. 1986, 41, 253–258. DOI: 10.1515/znb-1986-0217.
   Google Scholar
• Schonberg, A.; Badran, N.; Strakowsky, N. A. Furo-Chromones and Coumarins. VII Degradation of Visnagin, Khellin and Related Substances; Experiments with Chromic Acid and Hydrogen Peroxide; and a Synthesis of Eugenitin. J. Am. Chem. Soc. 1953, 75, 4992. DOI: 10.1021/ja01116a032.
   Web of Science ®Google Scholar
• Turner, J. A.; Jacks, W. S. Acylation of Ester Enolates by N-methoxy-N-Methylamides: An Effective Synthesis of α-Keto Esters. J. Org. Chem. 1989, 54, 4229–4231. DOI: 10.1021/jo00278a047.
   Web of Science ®Google Scholar
• Yilmaz, M.; Uzunalioglu, N.; Pekel, A. T. Manganese(III) Acetate Based Oxidative Cyclizations of 3-Oxopropanenitriles with Conjugated Alkenes and Synthesis of 4,5-Dihydrofuran-3-Carbonitriles Containing Heterocycles. Tetrahedron 2005, 61, 8860–8867. DOI: 10.1016/j.tet.2005.07.019.
   Web of Science ®Google Scholar
• Yılmaz, E. V. B.; Yılmaz, M.; Öktemer, A. Radical Cyclizations of Conjugated Esters and Amides with 3-Oxopropanenitriles Mediated by Manganese (III) Acetate. Arkivoc 2011, 2011, 363–376. DOI: 10.3998/ark.5550190.0012.230.
   Web of Science ®Google Scholar
• Abdel-Aziem, A.; Baaiu, B. B.; Abdelhamid, A. O. Synthesis and Evaluation of Antimicrobial Activity of Some Novel Heterocyclic Compounds from 5-Bromosalicylaldehyde. J. Heterocylic Chem 2017, 54, 3471-80. DOI: 10.1002/jhet.2970.
   Web of Science ®Google Scholar
• Wang, H.; Wang, Z.; Wang, Y.-L.; Zhou, R.-R.; Wu, G.-C.; Yin, S.-Y.; Yan, X.; Wang B., N-Bromosuccinimide (NBS)-Catalyzed C − H Bond Functionalization: An Annulation of Alkynes with Electron Withdrawing Group (EWG)-Substituted Acetyl Indoles for the Synthesis of Carbazoles. Org. Lett. 2017, 19, 6140–6143. DOI: 10.1021/acs.orglett.7b03021.
   PubMed Web of Science ®Google Scholar
• Wen, L.-R.; Xie, H.-Y.; Li, M. A Basic Ionic Liquid Catalyzed Reaction of Benzothiazole, Aldehydes, and 5,5‐Dimethyl‐1,3‐Cyclohexanedione: Efficient Synthesis of Tetrahydrobenzo[b]Pyrans. J. Heterocyclic Chem. 2009, 46, 954–959. DOI: 10.1002/jhet.183.
   Web of Science ®Google Scholar
• Schafer, V. H.; Gewald, K. Zur Chemie des 4-Phenyl-thiazoly-(2-acetonitrils). J. Prakt. Chemie. 1974, 316, 684–692. DOI: 10.1002/prac.19743160421.
   Google Scholar
• Belokon, Y. V.; Kovalenko, S. N.; Silin, A. V.; Nikitchenko, V. M. Ensembles of Rings with a Coumarin Unit. 1. Synthesis of 3-(2-R-Thiazol-4-yl)- and 3-(4-R-Thiazol-2-yl)Coumarins. Chem. Heterocycl. Compd. 1997, 33, 1167–1176. DOI: 10.1007/BF02290865.
   Google Scholar
• Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A.; et al. Feasibility Of a High-Flux Anticancer Drug Screen Using a Diverse Panel of Cultured Human Tumor Cell Lines. J. Natl. Cancer Inst. 1991, 83, 757–766. DOI: 10.1093/jnci/83.11.757.
   PubMed Web of Science ®Google Scholar
• Shoemaker, R. H. The NCI60 Human Tumour Cell Line Anticancer Drug Screen. Nat. Rev. Cancer 2006, 10, 813–823. DOI: 10.1038/nrc1951.
   Web of Science ®Google Scholar
• Boyd, M. R.; Paull, K. D. Some Practical Considerations and Applications of the National Cancer Institute in Vitro Anticancer Drug Discovery Screen. Drug Dev. Res. 1995, 34, 91–109. DOI: 10.1002/ddr.430340203.
   Web of Science ®Google Scholar