Sodium Perborate Tetrahydrate–Mediated Transformations of 2′-Hydroxychalcones to Flavanones, Flavones, and 3′, 5′-Diiodoflavone Under Mild, Environmentally Friendly Conditions

REFERENCES

• (a) 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 ; (b) 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 .
   PubMed Web of Science ®Google Scholar
• 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 2′-OH flavanone inhibit metastasis of lung cancer cells via down-regulation of proteinases activities and MAPK pathway . Chem-Biol. Interact. 2007 , 167 , 193 – 206 .
   PubMed Web of Science ®Google Scholar
• (a) 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 ; (b) 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 ; (c) 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 .
   PubMed Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• (a) Paredes , A. ; Alzuru , M. ; Mendez , J. ; Rodriguez-Ortega , M. Anti-sindbis activity of flavanones hesperetin and naringenin . Biol. Pharm. Bull. 2003 , 26 , 108 – 109 ; (b) 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 .
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• Biddle , M. M. ; Lin , M. ; Scheidt , K. A. Catalytic enantioselective synthesis of flavanones and chromanones . J. Am. Chem. Soc. 2007 , 129 , 3830 – 3831 .
   PubMed Web of Science ®Google Scholar
• 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 .
   Google Scholar
• Kagawa , H. ; Takahashi , T. ; Uno , M. ; Ohta , S. ; Harigaya , Y. Synthesis of deuterium-labeled flavanones . Chem. Pharm. Bull. 2004 , 52 , 953 – 956 .
   PubMed Web of Science ®Google Scholar
• Patonay , T. ; Litkei , G. ; Zsuga , M. ; Kiss , A. A simple procedure for the cyclization of 2′-hydroxychalcone into flavanones . Org. Prep. Proced. Int. 1984 , 16 , 315 – 319 .
   Web of Science ®Google Scholar
• Tanaka , K. ; Sugino , T. Efficient conversion of 2′-hydroxychalcones into flavanones and flavanols in a water suspension medium . Green Chem. 2001 , 3 , 133 – 134 .
   Web of Science ®Google Scholar
• 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 .
   Google Scholar
• (a) Macquarrie , D. J. ; Nazih , R. ; Sebti , S. KF/natural phosphate as an efficient catalyst for synthesis of 2′-hydroxychalcones and flavanones . Green Chem. 2002 , 4 , 56 – 59 ; (b) 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 .
   Web of Science ®Google Scholar
• Maruyama , K. ; Tamanaka , K. ; Nishinaga , A. ; Inada , A. ; Nakanishi , T. Conversion of 2′-hydroxychalcones to flavanones catalyzed by cobalt Schiff base complex . Tetrahedron Lett. 1989 , 30 , 4145 – 4148 .
   Web of Science ®Google Scholar
• Ahmed , N. ; Ali , H. ; van Lier , J. E. Silica gel–supported InBr3 and InCl3: New catalysts for the facile and rapid oxidation of 2′-hydroxychalcones and flavanones to their corresponding flavones under solvent-free conditions . Tetrahedron Lett. 2006 , 46 , 253 – 256 .
   Web of Science ®Google Scholar
• (a) Kaneda , K. ; Arai , T. Mechanistic approach to the cyclization reaction of a 2′-hydroxychalcone analogue with light and solvent . Org. Biomol. Chem. 2003 , 1 , 2041 – 2043 ; (b) Maki , Y. ; Shimada , K. ; Sako , M. ; Hirota , K. Photo-oxidative cyclisation of 2′-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 ; (c) Pandey , G. ; Krishna , A. ; Kumaraswamy , G. Photosensitized (set) conversion of 2′-hydroxychalcones to flavonoids: A probable biogenetic pathway . Tetrahedron Lett. 1987 , 28 , 4615 – 4616 ; (d) Matsushima , R. ; Kageyama , H. Photochemical cyclization of 2′-hydroxychalcones . J. Chem. Soc. Perkin Trans. 1985 , 2 743 – 748 ; (e) Matsushima , R. ; Hirao , I. Photocyclization of 2′-hydroxychalcones to 4-flavanones . Bull. Chem. Soc. Jpn. 1980 , 53 , 518 – 522 ; (f) Stermitz , F. R. ; Adamovics , J. A. ; Geigert , J. Synthesis and photoreactions of sorbophenones: A photochemical synthesis of flavone . Tetrahedron 1975 , 31 , 1593 – 1595 .
   PubMed Web of Science ®Google Scholar
• 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 .
   Google Scholar
• Sanicanin , Z. ; Tabakovic , I. Electrochemical transformations of 2′-hydroxychalcones into flavanoids . Tetrahedron Lett. 1986 , 27 , 407 – 408 .
   Web of Science ®Google Scholar
• (a) 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; (b) 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; (c) Ganguly , N. C. ; Mondal , P. Iodine-mediated efficient Beckmann rearrangement of ketoximes to amides under mild neutral conditions. Synthesis 2010, 3705–3709; (d) 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; (e) 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 (f) 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.
   Google Scholar
• (a) McKillop , A. ; Sanderson , W. R. Sodium perborate and sodium percarbonate: Further applications in organic synthesis . J. Chem. Soc, Perkin Trans. 1 2000 , 471 – 476 ; (b) Muzart , J. Sodium perborate and sodium percarbonate in organic synthesis . Synthesis 1995 , 1325 – 1347 ; (c) McKillop , A. ; Sanderson , W. R. Sodium perborate and sodium percarbonate: Cheap, safe, and versatile oxidizing agents for organic synthesis . Tetrahedron 1995 , 51 , 6145 – 6166 ; (d) 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 ; (e) There is one literature precedent of use of SPB as a substoichiometric co-oxidant in combination with trifluoromethanesulfonic acid for monohydroxylation of arenes; 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 .
   Google Scholar
• (a) Kumar , K. H. ; Perumal , P. T. A simple and facile solventless procedure for the cyclization of 2′-amino- and 2′-hydroxy-chalcones using silica-supported sodium hydrogen sulphate as heterogenous catalyst . Canadian J. Chem. 2006 , 84 , 1079 – 1083 ; (b) 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 ; (c) Sagreraa , G. ; Seoane , G. Acidic rearrangement of (benzyloxy)chalcones: A short synthesis of chamanetin . Synthesis 2009 , 4190 – 4202 ; (d) Kumar , D. ; Patel , G. ; Mishra , B. G. ; Varma , R. S. Eco-friendly polyethylene glycol–promoted Michael addition reactions of α, β-unsaturated carbonyl compounds . Tetrahedron Lett. 2008 , 49 , 6974 – 6976 .
   Web of Science ®Google Scholar
• (a) Eliel , E. L. ; Wilen , S. H. Stereochemistry of Organic Compounds ; John Wiley & Sons : New York , 1994 ; p. 684 ; (b) 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 .
   Google Scholar
• (a) Straub , T. S. Epoxidation of α, β-unsaturated ketones with sodium perborate . Tetrahedron Lett. 1995 , 36 , 663 – 664 ; (b) 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 .
   Web of Science ®Google Scholar
• (a) 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; (b) 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; (c) 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; (d) Kumar , K. H. ; Perumal , P. T. A novel one-pot oxidative cyclization of 2′-amino and 2′-hydroxychalcones employing FeCl3 × 6H2O–methanol: Synthesis of 4-alkoxy-2-aryl-quinolines and flavones. Tetrahedron 2007, 63, 9531–9535
   PubMed Web of Science ®Google Scholar
• (a) Butler , A. ; Walker , J. V. Marine haloperoxidases . Chem. Rev. 1993 , 93 , 1937 – 1944 ; (b) Sovak , M. Radiocontrast Agents: Handbook of Experimental Pharmacology; Springer: Berlin, 1993 .
   Web of Science ®Google Scholar
• Chen , F. C. ; Chang , T. C. ; Chen , T. S. Synthesis of 8- and 3′-iodoflavones and related compounds . J. Org. Chem. 1962 , 27 , 85 – 87 , and references cited therein .
   Web of Science ®Google Scholar
• Liu , H. ; Tan , H.-C. Iodobenzene-catalysed iodolactonisation using sodium perborate monohydrate as oxidant . Tetrahedron Lett. 2007 , 48 , 8220 – 8222 .
   Web of Science ®Google Scholar