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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 13
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Articles

One-pot three-component synthesis of a new series of tetrahydrobenzofuran-chromone conjugates

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Pages 1974-1981 | Received 22 Dec 2020, Published online: 10 May 2021

References

  • Machado, N. F. L.; Marques, M. P. M. Bioactive Chromone Derivatives - Structural Diversity. CBC. 2010, 6, 76–89. DOI: 10.2174/157340710791184859.
  • Zhang, H.; Li, F.; Zhu, P.; Liu, J.; Yao, H.; Jiang, J.; Ye, W.; Wu, X.; Xu, J. Synthesis and Biological Evaluation of Oxygen-Containing Heterocyclic Ring-Fused 23-Hydroxybetulinic Acid Derivatives as Antitumor Agents. Chem. Biol. Drug Des. 2015, 86, 424–431. DOI: 10.1111/cbdd.12543.
  • Ellis, G. P. Chromenes, Chromanones, and Chromones—Introduction. In Chemistry of Heterocyclic Compounds. John Wiley & Sons, Inc., New York, 2008, p. 1–10.
  • Gabor, M. Anti-Inflammatory and anti-Allergic Properties of Flavonoids. Prog. Clin. Biol. Res. 1986, 213, 471–480.
  • Rival, Y.; Grassy, G.; Taudou, A.; Ecalle, R. Antifungal Activity in Vitro of Some Imidazo[1,2-a]Pyrimidine Derivatives. Eur. J. Med. Chem. 1991, 26, 13–18. DOI: 10.1016/0223-5234(91)90208-5.
  • Teimouri, M. B.; Akbari-Moghaddam, P.; Golbaghi, G. Pseudo-Five-Component Reaction between 3-Formylchromones, Meldrum’s Acid, Isocyanides and Primary Arylamines: Diversity-Oriented Synthesis of Novel Chromone-Containing Peptidomimetics. ACS Comb. Sci. 2011, 13, 659–666. DOI: 10.1021/co200125a.
  • Yagi, A.; Kabash, A.; Okamura, N.; Haraguchi, H.; Moustafa, S. M.; Khalifa, T. I. Antioxidant, Free Radical Scavenging and anti-Inflammatory Effects of Aloesin Derivatives in Aloe Vera. Planta. Med. 2002, 68, 957–960. DOI: 10.1055/s-2002-35666.
  • Gonzalez, A. G.; Darias, V.; Estevez, E.; Vivas, J. M. Chemotherapeutic Study of Chromones from Spanish Cneoraceae. Planta Med. 1983, 47, 56–58. DOI: 10.1055/s-2007-969950.
  • Teimouri, M. B.; Asnaashari, B.; Moayedi, M.; Naderi, S. Diastereoselective One-Pot Synthesis of Succinimides Bearing a Chromone Unit. Synlett. 2014, 26, 101–107. DOI: 10.1055/s-0034-1378926.
  • Teimouri, M. B.; Mashayekhi, F.; Alishaei, E. Synthesis of 2-(3-Chromonyl)-2-Acyloxycarboxamides via Multicomponent Reactions of Isocyanides. J. Iran. Chem. Soc. 2016, 13, 583–590. DOI: 10.1007/s13738-015-0769-7.
  • (a) Zghab, I.; Trimeche, B.; Mansour, M. B.; Hassine, M.; Touboul, D.; Jannet, H. B. Regiospecific Synthesis, Antibacterial and Anticoagulant Activities of Novel Isoxazoline Chromene Derivatives. Arab. J. Chem. 2017, 10, S2651–S2658. DOI: 10.1016/j.arabjc.2013.10.008. (b) Dey, S.; Lo, H.-J.; Wong, C.-H. An Efficient Modular One-Pot Synthesis of Heparin-Based Anticoagulant Idraparinux. J. Am. Chem. Soc. 2019, 141, 10309–10314. doi:10.1021/jacs.9b03266. (c) Dey, S.; Lo, H.-J.; Wong, C.-H. Programmable One-Pot Synthesis of Heparin Pentasaccharide Fondaparinux. Org. Lett. 2020, 22, 4638–4642. doi:10.1021/acs.orglett.0c01386.
  • Mazzei, M.; Balbi, A.; Roma, G.; Di Braccio, M.; Leoncini, G.; Buzzi, E.; Maresca, M. Synthesis and anti-Platelet Activity of Some 2-(Dialkylamino)Chromones. Eur. J. Med. Chem. 1988, 23, 237–242. DOI: 10.1016/0223-5234(88)90005-0.
  • Teimouri, M. B.; Zolfaghari, F.; Naderi, S. Furochromone-Isatin Conjugates via an Uncatalyzed Diastereoselective [4 + 1] Cycloaddition/Tautomerization/Friedel-Crafts Hydroxyalkylation Domino Reaction. Tetrahedron 2017, 73, 262–271. DOI: 10.1016/j.tet.2016.12.010.
  • Teimouri, M. B.; Eskandari, M. An Efficient Synthesis of Novel Chromone-Containing Furopyrimidines. J. Chem. Res. 2011, 35, 500–505. DOI: 10.3184/174751911X13146322603355.
  • Gamal-Eldeen Amira, M.; Djemgou Pierre, C.; Tchuendem, M.; Ngadjui Bonaventure, T.; Tane, P.; Toshifumi, H. Anti-Cancer and Immunostimulatory Activity of Chromones and Other Constituents from Cassia Petersiana. Z. Naturforsch. C. 2007, 62, 331–338. DOI: 10.1515/znc-2007-5-622.
  • Gautam, R.; Jachak, S. M.; Kumar, V.; Mohan, C. G. Synthesis, Biological Evaluation and Molecular Docking Studies of Stellatin Derivatives as Cyclooxygenase (COX-1, COX-2) Inhibitors and anti-Inflammatory Agents. Bioorg. Med. Chem. Lett. 2011, 21, 1612–1616. DOI: 10.1016/j.bmcl.2011.01.116.
  • Subbareddy, C. V.; Sumathi, S. One-Pot Three-Component Protocol for the Synthesis of Indolyl-4H-Chromene-3-Carboxamides as Antioxidant and Antibacterial Agents. New J. Chem. 2017, 41, 9388–9396. DOI: 10.1039/C7NJ00980A.
  • Gaspar, A.; Matos, M. J.; Garrido, J.; Uriarte, E.; Borges, F. Chromone: A Valid Scaffold in Medicinal Chemistry. Chem. Rev. 2014, 114, 4960–4992. DOI: 10.1021/cr400265z.
  • DeSimone, R. W.; Currie, K. S.; Mitchell, S. A.; Darrow, J. W.; Pippin, D. A. Privileged Structures: Applications in Drug Discovery. CCHTS. 2004, 7, 473–493. DOI: 10.2174/1386207043328544.
  • Horton, D. A.; Bourne, G. T.; Smythe, M. L. The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged Substructures. Chem. Rev. 2003, 103, 893–930. DOI: 10.1021/cr020033s.
  • Gao, X.-M.; Yu, T.; Lai, F. S. F.; Pu, J.-X.; Qiao, C.-F.; Zhou, Y.; Liu, X.; Song, J.-Z.; Luo, K. Q.; Xu, H.-X. Novel Polyisoprenylated Benzophenone Derivatives from Garcinia paucinervis. Tetrahedron Lett. 2010, 51, 2442–2446. DOI: 10.1016/j.tetlet.2010.02.147.
  • Hsieh, M.-J.; Chen, M.-K.; Yu, Y.-Y.; Sheu, G.-T.; Chiou, H.-L. Psoralen Reverses Docetaxel-Induced Multidrug Resistance in A549/D16 Human Lung Cancer Cells Lines. Phytomedicine 2014, 21, 970–977. DOI: 10.1016/j.phymed.2014.03.008.
  • Patil, A. D.; Freyer, A. J.; Killmer, L.; Offen, P.; Carte, B.; Jurewicz, A. J.; Johnson, R. K. Frondosins, Five New Sesquiterpene Hydroquinone Derivatives with Novel Skeletons from the Sponge Dysidea Frondosa: Inhibitors of Interleukin-8 Receptors. Tetrahedron 1997, 53, 5047–5060. DOI: 10.1016/S0040-4020(97)00205-6.
  • Hallock, Y. F.; Cardellina, J. H.; Boyd, M. R. (-) Frondosins a and D, HIV-Inhibitory Sesquiterpene Hydroquinone Derivatives from Euryspongia sp. Nat. Prod. Lett. 1998, 11, 153–160. DOI: 10.1080/10575639808041212.
  • Seitz, M.; Dewald, B.; Gerber, N.; Baggiolini, M. Enhanced Production of Neutrophil-Activating Peptide-1/Interleukin-8 in Rheumatoid Arthritis. J. Clin. Invest. 1991, 87, 463–469. DOI: 10.1172/JCI115018.
  • Reiter, M.; Torssell, S.; Lee, S.; MacMillan, D. W. C. The Organocatalytic Three-Step Total Synthesis of (+)-Frondosin B. Chem. Sci. 2010, 1, 37–42. DOI: 10.1039/c0sc00204f.
  • (a) Cheng, C.-W.; Zhou, Y.; Pan, W.-H.; Dey, S.; Wu, C.-Y.; Hsu, W.-L.; Wong, C.-H. Hierarchical and Programmable One-Pot Synthesis of Oligosaccharides. Nat. Commun. 2018, 9, 5202–5209. (b) Bagley, M. C.; Dale, J. W.; Bower, J. A New One-Pot Three-Component Condensation Reaction for the Synthesis of 2,3,4,6-Tetrasubstituted Pyridines. Chem. Commun. 2002, 1682–1683. DOI: 10.1039/B203900A. doi:10.1038/s41467-018-07618-8.
  • Akritopoulou-Zanze, I. Isocyanide-Based Multicomponent Reactions in Drug Discovery. Curr. Opin. Chem. Biol. 2008, 12, 324–331. DOI: 10.1016/j.cbpa.2008.02.004.
  • Aleksandr, V. I.; Ya, A. I.; Vladimir, M. K.; Mikhail Yu, K.; Aleksei, P. I. Multicomponent Reactions of Isocyanides in the Synthesis of Heterocycles. Russ. Chem. Rev. 2010, 79, 787–817. DOI: 10.1070/RC2010v079n09ABEH004086.
  • Teimouri, M. B.; Mansouri, F. One-Pot Three-Component Access to Pyranocyclopentendiones. J. Chem. Res. 2010, 34, 330–332. DOI: 10.3184/030823410X12753056300098.
  • Cano, P. A.; Islas-Jácome, A.; González-Marrero, J.; Yépez-Mulia, L.; Calzada, F.; Gámez-Montaño, R. Synthesis of 3-Tetrazolylmethyl-4H-Chromen-4-Ones via Ugi-Azide and Biological Evaluation against Entamoeba histolytica, Giardia lamblia and Trichomona vaginalis. Bioorg. Med. Chem. 2014, 22, 1370–1376. DOI: 10.1016/j.bmc.2013.12.069.
  • Teimouri, M. B.; Bazhrang, R.; Eslamimanesh, V.; Nouri, A. Reaction between Isocyanides and Dialkyl Acetylenedicarboxylates in the Presence of Strong CH-Acids: One-Pot Synthesis of Highly Functionalized Annulated 4H-Pyrans. Tetrahedron 2006, 62, 3016–3020. DOI: 10.1016/j.tet.2006.01.039.
  • Dömling, A. Recent Advances in Isocyanide-Based Multicomponent Chemistry. Curr. Opin. Chem. Biol. 2002, 6, 306–313. DOI: 10.1016/S1367-5931(02)00328-9.
  • Shaabani, A.; Maleki, A.; Rezayan, A. H.; Sarvary, A. Recent Progress of Isocyanide-Based Multicomponent Reactions in Iran. Mol. Divers. 2011, 15, 41–68. DOI: 10.1007/s11030-010-9258-1.
  • Ruijter, E.; Scheffelaar, R.; Orru, R. V. A. Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity. Angew. Chem. Int. Ed. 2011, 50, 6234–6246. DOI: 10.1002/anie.201006515.
  • Váradi, A.; Palmer, T.; Notis Dardashti, R.; Majumdar, S. Isocyanide-Based Multicomponent Reactions for the Synthesis of Heterocycles. Molecules 2015, 21, 19–41. DOI: 10.3390/molecules21010019.
  • Koopmanschap, G.; Ruijter, E.; Orru, R. V. A. Isocyanide-Based Multicomponent Reactions towards Cyclic Constrained Peptidomimetics. Beilstein J. Org. Chem. 2014, 10, 544–598. DOI: 10.3762/bjoc.10.50.

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