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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 24
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Original Articles

Molecular Iodine: An Efficient and Environment Friendly Catalyst for the Synthesis of 3,5-Bis-(arylmethylidene)-tetrahydropyran-4-ones

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Pages 3728-3733 | Received 28 Aug 2009, Published online: 09 Nov 2010

REFERENCES

  • (a) Deli , J. ; Lorand , T. ; Szabo , D. ; Foldesi , A. Potential bio-active pyrimidine Derivatives 1: 2-Amino-4-aryl-8-arylidene-3,4,5,6,7,8-hexahydrochinazolines . Pharmazie 1984 , 39 , 539 – 540 ; (b) Guilford , W. J. ; Shaw , K. J. ; Dallas , J. L. ; Koovakkat , S. ; Lee , W. ; Liang , A. ; Light , D. R. ; McCarrick , M. A. ; Whitlow , M. ; Ye , B. ; Morrissey , M. M. Synthesis, characterization, and structure–activity relationships of amidine-substituted (bis)benzylidene-cycloketone olefin isomers Novel Bisarylmethylidenes of Cyclic Enones as potent and selective factor Xa inhibitors . J. Med. Chem. 1999 , 42 , 5415 – 5425 ; (c) Artico , M. ; Di Santo , R. ; Costi , R. ; Novellino , E. ; Greco , G. ; Massa , S. ; Tramintano , E. ; Marongiu , M. E. ; De Montis , A. ; La Colla , P. Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 integrase: Synthesis, biological evaluation, and molecular modeling . J. Med. Chem. 1998 , 41 , 3948 – 3960 ; (d) Jia , Z. C. ; Quail , J. W. ; Arora , V. K. ; Dimmock , J. R. Structure of 3,5-bis(benzylidene)-1-methyl-4-piperidone methobromide hemithanol solvate . Acta Cryst., Sect. C. 1989 , 45 , 1117 – 1118 ; (e) Gangadhara , K. K. Synthesis and characterization of photo-cross-linkable main-chain liquid-crystalline polymers containing bis(benzylidene)cycloalkanone units . Polymer 1995 , 36 , 1903 – 1910 .
  • (a) Ward , D. E. ; Nixey , T. E. ; Gai , Y. ; Hrapchak , M. J. ; Abaee , M. S. Intramolecular Diels–Alder reactions of 2H-thiopyran dienes . Can. J. Chem. 1996 , 74 , 1418 – 1436 ; (b) Ward , D. E. ; Abaee , M. S. Intramolecular Diels−Alder Reaction by Self-Assembly of the Components on a Lewis Acid Template . Org. Lett. 2000 , 2 , 3937 – 3940 ; (c) Ward , D. E. ; Sales , M. ; Chuk , C. M. ; Jianheng , S. ; Pradip , K. S. ; Cheng , G. Influence of the β-Alkoxy Group on the Diastereoselectivity of Aldol Reactions of Tetrahydro-4H-thiopyran-4-one with 4-Alkoxytetrahydro-2H-thiopyran-3-carboxaldehydes . J. Org. Chem. 2001 , 67 , 1618 – 1629 .
  • Mai , A. ; Cheng , D. ; Bedford , M. T. ; Valente , S. ; Nebbioso , A. ; Perrone , A. ; Brosch , G. ; Sbardella , G. ; De Bellis , F. ; Miceli , M. ; Altucci , L. Epigenetic multiple ligands: Mixed histone/protein methyltransferase, acetyltransferase, and class III deacetylase (sirtuin) inhibitors . J. Med. Chem. 2008 , 51 ( 7 ), 2279 – 2290 .
  • Abaee , M. S. ; Mojtahedi , M. M. ; Zahedi , M. M. ; Sharifi , R. A highly efficient method for solvent-free synthesis of bisarylmethylidenes of pyranones and thiopyranones . Heteroatom Chem. 2007 , 18 ( 1 ), 44 – 49 .
  • Abaee , M. S. ; Mojtahedi , M. M. ; Zahedi , M. M. ; Bolourtchian , S. M. First highly efficient synthesis of bis(arylmethylidene)pyranones mediated by lithium perchlorate . Synth. Commun. 2006 , 36 ( 2 ), 199 – 206 .
  • Costi , R. ; Santo , R. D. ; Artico , M. ; Massa , S. ; Ragno , R. ; Loddo , R. ; La Colla , M. ; Tramontano , E. ; La Colla , P. ; Pani , A. 2,6-Bis(3,4,5-trihydroxybenzylydene) derivatives of cyclohexanone-novel potent HIV-1 integrase inhibitors that prevent HIV-1 multiplication in cell-based assays . Bioorg. Med. Chem. Lett. 2004 , 12 ( 1 ), 199 – 215 .
  • Abaee , M. S. ; Mojtahedi , M. M. ; Zahedi , M. M. ; Mesbah , A. W. ; Ghandchi , N. M. ; Massa , W. Phosphorus, Sulfur, Silicon. 2007 , 182 , 2891 – 2895 .
  • (a) 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 ; (b) Hessian , K. O. ; Flynn , B. L. Iodine-induced reaction cascades for the rapid construction of variously substituted benzothiophenes . Org. Lett. 2003 , 5 , 4377 – 4380 .
  • (a) Madhusudana Reddy , M. B. ; Pasha , M. A. Molecular iodine catalyzed mild, effective and eco-friendly microwave assisted one-pot synthesis of 5-arylmethylidene-2-phenyloxazol-4-ones (azalactones) under solvent-free condition. Synth. Commun. 2009 (LSYC-2009-2879, In press); (b) Pasha , M. A. ; Jayashankara , V. P. ; Swamy , N. R. A simple and efficient procedure for the one pot synthesis of β-acetamido-β-aryl-propiophenones by molecular iodine catalyzed Tandem reaction. Synth. Commun. 2007, 37, 1551–1556; (c) Pasha , M. A. ; Jayashankara , V. P. Molecular iodine catalyzed synthesis of aryl-14H-dibenzo[a,j]xanthenes under solvent free condition. Bioorg. Med. Chem. Lett. 2007, 17, 621–623.

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