Sodium perborate tetrahydrate-mediated transformations of 2′-hydroxychalcones to flavanones, flavones, and 3′, 5′-diiodoflavone under mild, environmentally friendly conditions

Synthetic Communications

Volumn 43, Issue 10, 2013, Pages 1351-1361

  Ganguly, Nemai C ^a   Chandra, Sumanta ^a   Barik, Sujoy Kumar ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

2 hydroxychalcone; 3 ; 5 Diiodoflavone; Flavanone; Flavone; Sodium perborate tetrahydrate

Indexed keywords

2' HYDROXYCHALCONE; 3',5' DIIODOFLAVONE; ACETIC ACID; ACETONITRILE; BENZENE DERIVATIVE; BORON DERIVATIVE; CHALCONE DERIVATIVE; CHROMONE DERIVATIVE; DIACETOXYIODOBENZENE; FLAVANONE DERIVATIVE; FLAVONE DERIVATIVE; KETONE DERIVATIVE; PERBORATE SODIUM; QUATERNARY AMMONIUM DERIVATIVE; TETRA N BUTYLAMMONIUM IODIDE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CONTROLLED STUDY; CYCLIZATION; DRUG TRANSFORMATION; IODINATION; ONE POT SYNTHESIS; OXIDATION; STOICHIOMETRY;

EID: 84876179341     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.633734     Document Type: Article

References (56)

1. Agarwal, C.; Tyagi, A.; Kaur, M.; Agarwal, R. Silibinin inhibits constitutive activation of Stat3, and causes caspase activation and apoptotic death of human prostate carcinoma DU145 cells. Carcinogenesis 2007, 28, 1463-1470;
2. Cabrera, M.; Simoens, M.; Falchi, G.; Lavaggi, M. L.; Piro, O. E.; Castellano, E. E.; Vidal, A.; Azqueta, A.; Monge, A.; Lopez de Cerain, A.; Sagrera, G.; Seoane, G.; Cerecetto, H.; Gonzalez, M. Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure-activity relationships. Bioorg. Med. Chem. 2007, 15, 3356-3367.
3. Hsiao, Y. C.; Kuo, W. H.; Chen, P. N.; Chang, H. R.; Lin, T. H.; Yang, W. E.; Hsieh, Y. S.; Chu, S. C. Flavanone and 20-OH flavanone inhibit metastasis of lung cancer cells via down-regulation of proteinases activities and MAPK pathway. Chem-Biol. Interact. 2007, 167, 193-206.
4. Varga, Z.; Seres, I.; Nagy, E.; Ujhelyi, L.; Balla, G.; Balla, J.; Antus, S. Structure prerequisite for antioxidant activity of silybin in different biochemical systems in vitro. Phytomedicine 2006, 13, 85-93;
5. Sun, J. M.; Yang, J. S.; Zhang, H. Two new flavanone glycosides of Jasminum lanceolarium and their anti-oxidant activities. Chem. Pharm. Bull. 2007, 55, 474-476;
6. Jung, H. A.; Jeong, D. M.; Chung, H. Y.; Lim, H. A.; Kim, J. Y.; Yoon, N. Y.; Choi, J. S. Re-evaluation of the antioxidant prenylated flavonoids from the roots of Sophora flavescens. Biol. Pharm. Bull. 2008, 31, 908-915.
7. Ward, F. E.; Garling, D. L.; Buckler, R. T.; Lawler, D. M.; Cummings, D. P. Antimicrobial 3-methylene flavanones. J. Med. Chem. 1981, 24, 1073-1077.
8. Paredes, A.; Alzuru, M.; Mendez, J.; Rodriguez-Ortega, M. Anti-sindbis activity of flavanones hesperetin and naringenin. Biol. Pharm. Bull. 2003, 26, 108-109;
9. Kim, H. K.; Jeon, W. K.; Ko, B. S. Flavanone glycosides from Citrus junos and their anti-influenza virus activity. Planta Med. 2001, 67, 548-549.
10. Vauzour, D.; Vafeiadou, K.; Rice-Evans, C.; Williams, R. J.; Spencer, J. P. E. Activation of pro-survival Akt and ERK1=2 signalling pathways underlie the anti-apoptotic effects of flavanones in cortical neurons. J. Neurochem. 2007, 103, 1355-1367.
11. Chen, H. Y.; Dykstra, K. D.; Birzin, E. T.; Frisch, K.; Chan, W.; Yang, Y. T.; Mosley, R. T.; DiNino, F.; Rohrer, S. P.; Schaeffer, J. M.; Hammond, M. L. Estrogen receptor ligands, part 1: The discovery of flavanoids with subtype selectivity. Bioorg. Med. Chem. Lett. 2004, 14, 1417-1421.
12. Biddle, M. M.; Lin, M.; Scheidt, K. A. Catalytic enantioselective synthesis of flavanones and chromanones. J. Am. Chem. Soc. 2007, 129, 3830-3831.
13. González, E. A.; Nazareno, M. A.; Borsarelli, C. D. Enthalpy-entropy compensation effect in the chalcone formation from naringin in water-ethanol mixtures. J. Chem. Soc., Perkin Trans. 2002, 2, 2052-2056, and references cited therein.
14. Kagawa, H.; Takahashi, T.; Uno, M.; Ohta, S.; Harigaya, Y. Synthesis of deuterium-labeled flavanones. Chem. Pharm. Bull. 2004, 52, 953-956.
15. Patonay, T.; Litkei, G.; Zsuga, M.; Kiss, A. A simple procedure for the cyclization of 20-hydroxychalcone into flavanones. Org. Prep. Proced. Int. 1984, 16, 315-319.
16. Tanaka, K.; Sugino, T. Efficient conversion of 20-hydroxychalcones into flavanones and flavanols in a water suspension medium. Green Chem. 2001, 3, 133-134.
17. Litkei, G.; Bognár, R.; Dinya, Z.; Dávid, E. R. In Topics in Flavonoid Chemistry and Biochemistry; L. Farkas, M. Gábor, F. Kállay (Eds.); Elsevier: Amsterdam, 1975, 110.
18. Macquarrie, D. J.; Nazih, R.; Sebti, S. KF=natural phosphate as an efficient catalyst for synthesis of 20-hydroxychalcones and flavanones. Green Chem. 2002, 4, 56-59;
19. Harwood, L. M.; Loftus, G. C.; Oxford, A.; Thomson, C. An improved procedure for cyclisation of chalcones to flavanones using celite-supported potassium fluoride in methanol: Total synthesis of bavachinin. Synth. Commun. 1990, 20, 649-657.
20. Maruyama, K.; Tamanaka, K.; Nishinaga, A.; Inada, A.; Nakanishi, T. Conversion of 20-hydroxychalcones to flavanones catalyzed by cobalt Schiff base complex. Tetrahedron Lett. 1989, 30, 4145-4148.
21. Ahmed, N.; Ali, H.; van Lier, J. E. Silica gel-supported InBr3 and InCl3: New catalysts for the facile and rapid oxidation of 20-hydroxychalcones and flavanones to their corresponding flavones under solvent-free conditions. Tetrahedron Lett. 2006, 46, 253-256.
22. Kaneda, K.; Arai, T. Mechanistic approach to the cyclization reaction of a 20-hydroxychalcone analogue with light and solvent. Org. Biomol. Chem. 2003, 1, 2041- 2043;
23. Maki, Y.; Shimada, K.; Sako, M.; Hirota, K. Photo-oxidative cyclisation of 20-hydroxychalcones leading to flavones induced by heterocycle N-oxides: High efficiency of pyrimido[5,4-g]pteridine N-oxide for the photochemical dehydrogenation. Tetrahedron 1988, 44, 3187-3194;
24. Pandey, G.; Krishna, A.; Kumaraswamy, G. Photosensitized (set) conversion of 20-hydroxychalcones to flavonoids: A probable biogenetic pathway. Tetrahedron Lett. 1987, 28, 4615-4616;
25. Matsushima, R.; Kageyama, H. Photochemical cyclization of 2′-hydroxychalcones. J. Chem. Soc. Perkin Trans. 1985, 2 743-748;
26. Matsushima, R.; Hirao, I. Photocyclization of 2′-hydroxychalcones to 4-flavanones. Bull. Chem. Soc. Jpn. 1980, 53, 518-522;
27. Stermitz, F. R.; Adamovics, J. A.; Geigert, J. Synthesis and photoreactions of sorbophenones: A photochemical synthesis of flavone. Tetrahedron 1975, 31, 1593-1595.
28. Goud, B. S.; Panneerselvam, K.; Zacharias, D. E.; Desiraju, G. R. Intramolecular Michael-type addition in the solid state. J. Chem. Soc., Perkin Trans. 2 1995, 325-330.
29. Sanicanin, Z.; Tabakovic, I. Electrochemical transformations of 2′-hydroxychalcones into flavanoids. Tetrahedron Lett. 1986, 27, 407-408.
30. Ganguly, N. C.; Barik, S. K.; A facile efficient mild deprotection protocol of 1,3-dithianes and 1,3-dithiolanes with 30% hydrogen peroxide and iodine catalyst in aqueous micellar system. Synthesis 2009, 1393-1399;
31. Ganguly, N. C.; Nayek, S.; Barik, S. K. Convenient, mild catalytic deprotection of oximes to carbonyl compounds with hydrogen peroxide and iodine catalyst in aqueous acetonitrile. Synth. Commun. 2009, 39, 4053-4061;
32. Ganguly, N. C.; Mondal, P. Iodine-mediated efficient Beckmann rearrangement of ketoximes to amides under mild neutral conditions. Synthesis 2010, 3705-3709;
33. Ganguly, N. C.; Barik, S. K.; Dutta, S. Ecofriendly iodination of activated aromatics and coumarins using potassium iodide and ammonium peroxodisulfate. Synthesis 2010, 1467-1472;
34. Ganguly, N. C.; Mondal, P. Mild, efficient, and greener dethioacetalization protocol using 30% hydrogen peroxide in catalytic combination with ammonium iodide. Synth. Commun. 2011, 41, 2374-2384
35. Ganguly, N. C.; Mondal, P.; Barik, S. K. Iodine in aqueous micellar environment: A mild, effective, ecofriendly catalytic system for expedient synthesis of bis(indolyl)methanes and 3-substituted indolyl ketones. Green Chem. Lett. Rev. 2012, 5, 73-81.
36. McKillop, A.; Sanderson, W. R. Sodium perborate and sodium percarbonate: Further applications in organic synthesis. J. Chem. Soc, Perkin Trans. 1 2000, 471-476;
37. Muzart, J. Sodium perborate and sodium percarbonate in organic synthesis. Synthesis 1995, 1325-1347;
38. McKillop, A.; Sanderson, W. R. Sodium perborate and sodium percarbonate: Cheap, safe, and versatile oxidizing agents for organic synthesis. Tetrahedron 1995, 51, 6145-6166;
39. Gómez, M. V.; Caballero, R.; Vázquez, E.; Moreno, A.; de la Hoz, A.; Díaz-Ortiz, A. Green and chemoselective oxidation of sulfides with sodium perborate and sodium percarbonate: Nucleophilic and electrophilic character of the oxidation system. Green Chem. 2007, 9, 331-336;
40. see Prakash, G. K. S.; Krass, N.; Wang, Q.; Olah, G. A. Oxyfunctionalization of hydrocarbons, 15: Electrophilic hydroxylation of aromatics with sodium perborate=trifluorometahne-sulfonic acid. Synlett 1991, 39-40.
41. Kumar, K. H.; Perumal, P. T. A simple and facile solventless procedure for the cyclization of 20-amino- and 20-hydroxy-chalcones using silica-supported sodium hydrogen sulphate as heterogenous catalyst. Canadian J. Chem. 2006, 84, 1079-1083;
42. Lee, J. I.; Jung, M. G.; Jung, H. J. A novel synthesis of flavanones from 2-hydroxybenzoic acids. Bull. Korean Chem. Soc. 2007, 28, 859-862;
43. Sagreraa, G.; Seoane, G. Acidic rearrangement of (benzyloxy)chalcones: A short synthesis of chamanetin. Synthesis 2009, 4190- 4202;
44. Kumar, D.; Patel, G.; Mishra, B. G.; Varma, R. S. Eco-friendly polyethylene glycol-promoted Michael addition reactions of a, b-unsaturated carbonyl compounds. Tetrahedron Lett. 2008, 49, 6974-6976.
45. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; p. 684;
46. Bradley, P. J.; Jarvis, T. C.; Johnson, D.; Mcdonnell, P. D.; Weathestone, T. A. P. Stereoelectronic effects in ring closure reactions. Tetrahedron Lett. 1983, 24, 2851-2854.
47. Straub, T. S. Epoxidation of α, β-unsaturated ketones with sodium perborate. Tetrahedron Lett. 1995, 36, 663-664;
48. Kim, D. Y.; Choi, Y. J.; Park, H. Y.; Joung, C. U.; Koh, K. O.; Mang, J. Y.; Jung, K.-Y. Enantioselective epoxidation of α, β-unsaturated ketones by phase-transfer catalysis using chiral quaternary ammonium salts. Synth. Commun. 2003, 33, 435-443.
49. Huang, X.; Tang, E.; Xu, W.-M.; Cao, J. Lewis acid-catalyzed solid-phase synthesis of flavonoids using selenium-bound resin. J. Comb. Chem. 2005, 7, 802-805;
50. Cui, S.-L.; Lin, X.-F. Wang, Y.-G. Novel and efficient synthesis of iminocoumarins via copper-catalyzed multicomponent reaction. Org. Lett. 2006, 8, 4517-4520;
51. Sarda, S. R.; Pathan, M. Y.; Paike, V. V.; Pachmase, P. R.; Jadhav, W. N.; Pawar, R. P. A facile synthesis of flavones using recyclable ionic liquid under microwave irradiation. Arkivoc 2006, 16, 43-48;
52. 2O-methanol: Synthesis of 4-alkoxy-2-aryl-quinolines and flavones. Tetrahedron 2007, 63, 9531-9535
53. Butler, A.; Walker, J. V. Marine haloperoxidases. Chem. Rev. 1993, 93, 1937-1944;
54. Sovak, M. Radiocontrast Agents: Handbook of Experimental Pharmacology; Springer: Berlin, 1993.
55. Chen, F. C.; Chang, T. C.; Chen, T. S. Synthesis of 8- and 30-iodoflavones and related compounds. J. Org. Chem. 1962, 27, 85-87, and references cited therein.
56. Liu, H.; Tan, H.-C. Iodobenzene-catalysed iodolactonisation using sodium perborate monohydrate as oxidant. Tetrahedron Lett. 2007, 48, 8220-8222.