A Convenient Synthesis of α,α’-Bis(substituted benzylidene)cycloalkanones Catalyzed by Y(TFA)₃

REFERENCES

• Das , B. , Thirupathi , P. , Mahender , I. and Reddy , K. R. 2006 . 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. , 247 : 182 – 185 .
   Web of Science ®Google Scholar
• Wang , L. M. , Sheng , J. , Tian , H. , Han , J. W. , Fan , Z. Y. and Qian , C. T. 2004 . A convenient synthesis of α,α′-bis(substituted benzylidene)cycloalkanones catalyzed by Yb(OTf)3 under solvent-free conditions . Synthesis , 2004 : 3060 – 3064 .
   Web of Science ®Google Scholar
• Kawamata , J. , Inoue , K. , Inabe , T. , Kiguchi , M. , Kato , M. and Taniguchi , Y. 1996 . Large second-harmonic generation coefficients of bis(benzylidine) cycloalkanones estimated by the second-harmonic wave generated with the evanescent wave technique . Chem. Phys. Lett. , 249 : 29 – 34 .
   Web of Science ®Google Scholar
• Dimmock , J. R. A. , Padmanilayam , M. P. , Zello , G. A. , Nienaber , K. H. , Allen , T. M. , Santos , C. L. , de Clercq , E. , Balzarini , J. , Manavathu , E. K. and Stables , J. P. 2003 . Cytotoxic analogues of 2,6-bis(arylidene)cyclohexanones . Eur. J. Med. Chem. , 38 : 169 – 177 .
   PubMed Web of Science ®Google Scholar
• Gangadhara , K. K. 1995 . Synthesis and characterization of photo-crosslinkable main-chain liquid-crystalline polymers containing bis(benzylidene) cycloalkanone units . Polymer , 36 : 1903 – 1910 .
   Web of Science ®Google Scholar
• Irie , K. and Watanabe , K. 1980 . Aldol condensations with metal(II) complex catalysts . Bull. Chem. Soc. Jpn. , 53 : 1366 – 1371 .
   Web of Science ®Google Scholar
• Iranpoor , N. and Kazemi , F. 1998 . RuCl3 catalyses aldol condensations of aldehydes and ketones . Tetrahedron , 54 : 9475 – 9480 .
   Web of Science ®Google Scholar
• Li , Z. , Zhang , Y. and Li , Q. 2000 . Samarium (III) iodide promoted preparation of α,α’-bis (substituted benzylidene)cyclohexanones from benzaldehydes and cyclohexanone . J. Chem. Res. , 2000 : 580 – 581 .
   Google Scholar
• Abaee , M. S. , Mojtahedi , M. M. , Sharifi , R. , Zahedi , M. M. , Abbasi , H. and Tabar-Heidar , K. 2006 . Facile synthesis of bis(arylmethylidene) cycloalkanones mediated by lithium perchlorate under solvent-free conditions . J. Iran. Chem. Soc. , 3 : 293 – 296 .
   Web of Science ®Google Scholar
• Tao , X. C. , Liu , R. Z. , Meng , Q. H. , Zhao , Y. Y. , Zhou , J. L. and Huang , Y. B. 2005 . The reaction of ketones with benzaldehyde catalyzed by TiCl4·2THF . J. Mol. Catal. A: Chem. , 225 : 239 – 243 .
   Web of Science ®Google Scholar
• Bigdeli , M. A. , Mahdavinia , G. H. , Jafari , S. and Hazarkhani , H. 2007 . Wet 2,4,6-trichloro[1,3,5]triazine (TCT) an efficient catalyst for synthesis of α,α′-bis(substituted-benzylidene) cycloalkanones under solvent-free conditions . Catal. Commun. , 8 : 2229 – 2231 .
   Web of Science ®Google Scholar
• Zhang , X. Y. , Fan , X. S. , Niu , H. Y. and Wang , J. J. 2003 . An ionic liquid as a recyclable medium for the green preparation of α,α′-bis (substituted benzylidene)cycloalkanones catalyzed by FeCl3·6H2O . Green Chem. , 5 : 267 – 269 .
   Web of Science ®Google Scholar
• Deng , G. S. and Ren , T. G. 2003 . Indium trichloride catalyzes aldol-condensations of aldehydes and ketones . Synth. Commun. , 33 : 2995 – 3001 .
   Web of Science ®Google Scholar
• Salehi , P. , Dabiri , M. , Zolfigol , M. A. and Fard , M. A. B. 2004 . Silica sulfuric acid as an efficient and reusable reagent for crossed-aldol condensation of ketones with aromatic aldehydes under solvent-free conditions . J. Braz. Chem. Soc. , 15 : 773 – 776 .
   Web of Science ®Google Scholar
• Salehi , P. , Khodaei , M. M. , Zolfigol , M. A. and Keyvan , A. 2002 . Solvent-free crossed aldol condensation of ketones with aromatic aldehydes mediated by magnesium hydrogensulfate . Monatsh. Chem. , 133 : 1291 – 1295 .
   Web of Science ®Google Scholar
• Esmaeili , A. A. , Tabas , M. S. , Nasseri , M. A. and Kazemi , F. 2005 . Solvent-free crossed aldol condensation of cyclic ketones with aromatic aldehydes assisted by microwave irradiation . Monatsh. Chem. , 136 : 571 – 576 .
   Web of Science ®Google Scholar
• Sekiguchi , Y. , Sasaoka , A. , Shimomoto, Fujioka , A. S. and Kotsuki , H. 2003 . High-pressure-promoted asymmetric aldol reactions of ketones with aldehydes catalyzed by l-proline . Synlett , 2003 : 1655 – 1658 .
   Google Scholar
• Krupoder , S. A. , Danilovich , V. S. , Miller , A. O. and Furin , G. G. 1995 . Polyfluorocarboxylates. I. Copper(II) trifluoroacetate and its analogues . J. Fluorine Chem. , 73 : 13 – 15 .
   Web of Science ®Google Scholar
• Adibi , H. , Samimi , H. A. and Beygzadeh , M. 2007 . Iron(III) trifluoroacetate and trifluoromethanesulfonate: Recyclable Lewis acid catalysts for one-pot synthesis of 3,4-dihydropyrimidinones or their sulfur analogues and 1,4-dihydropyridines via solvent-free Biginelli and Hantzsch condensation protocols . Catal. Comm. , 8 : 2119 – 2124 .
   Web of Science ®Google Scholar
• Adibi , H. and Jafari , H. 2007 . Facile protection of carbonyl compounds as oxathiolanes and transoxathioacetalization of oxyacetals promoted by iron(III) trifluoroacetate or trifluoromethanesulfonate as chemoselective and recyclable catalysts . J. Fluorine Chem. , 128 : 679 – 682 .
   Web of Science ®Google Scholar
• Khosropour , A. R. , Mohammadpoor-Baltork , I. and Ghorbankhani , H. 2006 . Bi(TFA)3 immobilized in [nbpy]FeCl4: An efficient catalyst system for the one-pot synthesis of 4,6-diarylpyrimidin-2(1H)-ones . Catal. Comm. , 7 : 713 – 716 .
   Web of Science ®Google Scholar
• Song , D. L. , Wang , R. X. , Chen , Y. L. , Zhang , S. H. , Liu , C. S. and Luo , G . 2008 . Copper(II) trifluoroacetate catalyzed synthesis of 3,4-dihydropyrimidin-2(1H)-ones . React. Kinet. Catal. Lett. , 95 : 385 – 390 .
   Google Scholar
• Song , D. L. , Chen , Y. L. , Wang , R. X. , Liu , C. S. , Jiang , H. and Luo , G. 2009 . Crossed-aldol condensation of cycloalkanones with aromatic aldehydes catalyzed by copper(II) trifluoroacetate . Prep. Biochem. Biotechnol. , 39 : 201 – 207 .
   PubMed Web of Science ®Google Scholar
• Yanagihara , N. , Gotoh , T. and Ogura , T. 1996 . Complex formations of silver(I) trifluoroacetate and trifluoromethanesulfonate with benzene and cyclohexene . Polyhedron , 15 : 4349 – 4354 .
   Web of Science ®Google Scholar