Iodine-Catalyzed Mild and Efficient Method for the Synthesis of Chalcones

REFERENCES

• Nielsen , S. F. ; Christensen , S. B. ; Cruciani , G. ; Kharazmi , A. ; Liljefors , T. Antileishmanial chalcones: Statistical design, synthesis, and three-dimensional quantitative structure–activity relationship analysis . J. Med. Chem. 1998 , 41 , 4819 – 4832 .
   PubMed Web of Science ®Google Scholar
• Dimmock , J. R. ; Kandepu , N. M. ; Hetherington , M. ; Quail , J. W. ; Pugazhenthi , U. ; Sudom , A. M. ; Chamankhah , M. ; Rose , P. ; Pass , E. ; Allen , T. M. ; Halleran , S. ; Szydlowski , J. ; Mutus , B. ; Tannous , M. ; Manavathu , E. K. ; Myers , T. G. ; Clercq , E. D. ; Balzarini , J. Cytotoxic activities of Mannich bases of chalcones and related compounds . J. Med. Chem. 1998 , 41 , 1014 – 1026 .
   PubMed Web of Science ®Google Scholar
• Bu , X. ; Zhao , L. ; Li , Y. A facile synthesis of 6-C-prenylflavanones . Synthesis 1997 , 1246 – 1248 .
   Google Scholar
• Bu , X. ; Li , Y. G. Synthesis of exiguaflavanone K and (±)-leachianone . J. Nat. Prod. 1996 , 59 , 968 – 969 .
   Web of Science ®Google Scholar
• Alcantara , A. R. ; Marinas , J. M. ; Sinisterra , J. V. Synthesis of 2′-hydroxychalcones and related compounds in interfacial solid–liquid conditions . Tetrahedron Lett. 1987 , 28 , 1515 – 1518 .
   Web of Science ®Google Scholar
• Climent , M. J. ; Corma , A. ; Iborra , S. ; Primo , J. Base catalysis for fine chemicals production: Claisen–Schmidt condensation on zeolites and hydrotalcites for the production of chalcones and flavanones of pharmaceutical interest . J. Catal. 1995 , 15 , 60 – 66 .
   Web of Science ®Google Scholar
• Daskiewicz , J. B. ; Comte , G. ; Barron , D. ; Pietro , A. D. ; Thomasson , F. Organolithium-mediated synthesis of prenylchalcones as potential inhibitors of chemoresistance . Tetrahedron Lett. 1999 , 40 , 7095 – 7098 .
   Web of Science ®Google Scholar
• Sebti , S. ; Solhy , A. ; Tahir , R. ; Boulaajaj , S. ; Mayoral , J. A. ; Fraile , J. M. ; Kossir , A. ; Oumimoun , H. Calcined sodium nitrate/natural phosphate: An extremely active catalyst for the easy synthesis of chalcones in heterogeneous media. Tetrahedron Lett. 2001, 42, 7953–7955.
   Web of Science ®Google Scholar
• Sebti , S. ; Solhy , A. ; Smahi , A. ; Kossir , A. ; Oumimoun , H. Dramatic activity enhancement of natural phosphate catalyst by lithium nitrate: An efficient synthesis of chalcones . Catal. Commun. 2002 , 3 , 335 – 339 .
   Web of Science ®Google Scholar
• Calloway , N. O. ; Green , L. D. Reactions in the presence of metallic halides, I: β-Unsaturated ketone formation as a side reaction in Friedel-Crafts acylations . J. Am. Chem. Soc. 1937 , 59 , 809 – 811 .
   Web of Science ®Google Scholar
• Sz'ell , T. ; Sohalr , I. New nitro chalcones . Can. J. Chem. 1969 , 47 , 1254 – 1258 .
   Web of Science ®Google Scholar
• Irie , K. ; Watanabe , K. Aldal condensations with metal(II) complex catalysts . Bull. Chem. Soc. Jpn. 1980 , 53 , 1366 – 1371 .
   Web of Science ®Google Scholar
• Mazza , L. ; Guaram , A. An improved synthesis of 1,3 dibenzyl-2-buten-1-ones (β-methyl chalcones) . Synthesis 1980 , 41 – 44 .
   Google Scholar
• Nakano , T. ; Irifune , S. ; Umano , S. ; Inada , A. ; Ishii , Y. ; Ogawa , M. Cross-condensation reactions of cycloalkanones with aldehydes and primary alcohols under the influence of zirconocene complexes . J. Org. Chem. 1987 , 52 , 2239 – 2244 .
   Web of Science ®Google Scholar
• Iranpoor , N. ; Kazemi , F. RuCl3 catalyses aldol condensations of aldehydes and ketones . Tetrahedron 1998 , 54 , 9475 – 9480 .
   Web of Science ®Google Scholar
• Narender , T. ; Papi Reddy , K. A simple and highly efficient method for the synthesis of chalcones by using borontrifluoride-etherate . Tetrahedron Lett. 2007 , 48 , 3177 – 3180 .
   Web of Science ®Google Scholar
• Huang , D. F. ; Wang , J. X. ; Hu , Y. L. A new solvent-free synthesis of α, α′-dibenzylidene cycloalkanones from acetals with cycloalkanones under microwave irradiation . Chin. Chem. Lett. 2003 , 14 , 333 – 334 .
   Web of Science ®Google Scholar
• Petrov , O. ; Ianova , Y. ; Gerova , M. SOCl2/EtOH: Catalytic system for synthesis of chalcones . Catal. Commun. 2008 , 9 , 315 – 316 .
   Web of Science ®Google Scholar
• Shen , J. ; Wang , H. ; Lia , H. ; Sun , Y. ; Liu , Z. Br⊘nsted acidic ionic liquids as dual catalyst and solvent for environmentally friendly synthesis of chalcone . J. Mol. Catal. A: Chem. 2008 , 280 , 24 – 28 .
   Web of Science ®Google Scholar
• Togo , H. ; Iida , S. Synthetic use of molecular iodine for organic síntesis . Synlett 2006 , 2159 – 2175 .
   Web of Science ®Google Scholar
• Lin , X.-F. ; Cui , S.-L. ; Wang , Y.-G. A highly efficient synthesis of 1,2,3,4-tetrahydroquinolines by molecular iodine-catalyzed domino reaction of anilines with cyclic enol ethers . Tetrahedron Lett. 2006 , 47 , 4509 – 4512 .
   Web of Science ®Google Scholar
• Chen , W.-Y. ; Lu , J. Molecular iodine–catalyzed one-pot synthesis of 1,5-benzodiazepine derivatives under solvent-free conditions . Synlett 2005 , 1337 – 1339 .
   Web of Science ®Google Scholar
• Royer , L. ; De , S. K. ; Gibbs , R. A. Iodine as a novel and efficient reagent for the synthesis of α-aminonitriles by a three-component condensation of carbonyl compounds, amines, and trimethylsilyl cyanide . Tetrahedron Lett. 2005 , 46 , 4595 – 4597 .
   Web of Science ®Google Scholar
• Banik , B. K. ; Fernandez , M. ; Alvarez , C. Iodine-catalyzed highly efficient Michael reaction of indoles under solvent-free condition . Tetrahedron Lett. 2005 , 46 , 2479 – 2482 .
   Web of Science ®Google Scholar
• Ko , S. ; Sastry , M. N. V. ; Lin , C. ; Yao , C.-F. Molecular iodine–catalyzed one-pot synthesis of 4-substituted-1,4-dihydropyridine derivatives via Hantzsch reaction. Tetrahedron Lett. 2005, 46, 5771–5774.
   Web of Science ®Google Scholar
• Wang , S.-Y. Molecular iodine . Synlett. 2004 , 2642 – 2643 .
   Web of Science ®Google Scholar
• Yadav , J. S. ; Reddy , B. V. S. ; Narayana Kumar , G. G. K. S. ; Swamy , T. Iodine as a versatile reagent for the Prins-cyclization: An expeditious synthesis of 4-iodotetrahydropyran derivatives . Tetrahedron Lett. 2007 , 48 , 2205 – 2208 .
   Web of Science ®Google Scholar
• Yadav , J. S. ; Reddy , B. V. S. ; Premalatha , K. ; Swamy , T. First example of the activation of polymethylhydrosiloxane with molecular iodine: A facile synthesis of 3,6-dihydropyran derivatives . Tetrahedron Lett. 2005 , 46 , 2687 – 2690 .
   Web of Science ®Google Scholar
• Yadav , J. S. ; Reddy , B. V. S. ; Rao , C. V. ; Chand , P. K. ; Prasad , A. R. Iodine-catalyzed stereo selective synthesis of allyl glycosides, glycosyl cyanides, and glycosyl azides . Synlett 2001 , 1638 – 1640 .
   Google Scholar
• Kumar , H. M. S. ; Reddy , B. V. S. ; Reddy , E. J. ; Yadav , J. S. Iodine-catalyzed mild and efficient tetrahydropyranylation/depyranylation of alcohols . Chem. Lett. 1999 , 9 , 857 – 858 .
   Web of Science ®Google Scholar
• Yadav , J. S. ; Reddy , B. V. S. ; Ruchi , J. ; Reddy , U. V. S. Iodine-catalyzed coupling of 4-hydroxyl proline with isatins: An expeditious synthesis of 3-pyrrolyl indolin-2-ones . J. Mol. Catal. A: Chem. 2007 , 278 , 38 – 41 .
   Google Scholar
• Pasha , M. A. ; Jayashankara , V. P. Synthesis of α, α′-bis(arylmethylidene) cycloalkanones catalyzed by molecular iodine: An improved procedure for the Claisen–Schmidt condensation . Indian J. Chem. 2007 , 46B , 1025 – 1027 .
   Google Scholar
• Das , B. ; Thirupathi , P. ; Mahender , I. ; Ravinder Reddy , K. Convenient and facile cross-aldol condensation catalyzed by molecular iodine: An efficient synthesis of α, α′-bis(substituted-benzylidene) cycloalkanones . J. Mol. Catal. A: Chem. 2006 , 247 , 182 – 185 .
   Web of Science ®Google Scholar
• Part 4 in the series Studies on Novel Synthetic Methodologies. CDRI Communication No. 7418.
   Google Scholar