Synthesis and Fluorescence Properties of α,α′-Bis(substituted-benzylidene)cycloalkanones Catalyzed by 1-Methyl-3(2-(sulfooxy)ethyl)-1H-imidazol-3-ium Chloride

REFERENCES

• Kawamata , J. ; Inoue , K. ; Inabe , T. ; Kiguchi , M. ; Kato , M. ; Taniguchi , Y. Large second-harmonic generation coefficients of bis(benzylidene)cycloalkanones estimated by the second-harmonic wave generated with the evanescent wave technique . Chem. Phys. Lett. 1996 , 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. ; Stables , J. P. Cytotoxic analogues of 2,6-bis (arylidene)cyclohexanones . Eur. J. Med. Chem. 2003 , 38 , 169 – 177 .
   PubMed Web of Science ®Google Scholar
• Gangadhara ; Kaushal , K. Synthesis and characterization of photo-crosslinkable main-chain liquid-crystalline polymers containing bis(benzylidene)cycloalkanone units . Polymer 1995 , 36 , 1903 – 1910 .
   Web of Science ®Google Scholar
• Warela , M. C. ; Dixon , S. M. ; Larn , K. S. ; Schore , N. E. Asymmetric epoxidation, Michael addition, and triple cascade reaction using polymer-supported, prolinol-based auxiliaries . Tetrahedron 2008 , 64 , 10087 – 10090 .
   Google Scholar
• Hathaway , B. A. An aldol condensation experiment using a number of aldehydes and ketones . J. Chem. Educ. 1987 , 64 , 367 – 368 .
   Web of Science ®Google Scholar
• Irie , K. ; Watanabe , K. Aldol condensations with metal(II) complex catalysts . Bull. Chem. Soc. Jpn. 1980 , 53 , 1366 – 1371 .
   Web of Science ®Google Scholar
• Nakano , T. ; Migita , T. A convenient synthesis of α,α′-bis(substituted-benzylidene) cycloalkanones . Chem. Lett. 1993 , 2157 – 2158 .
   Google Scholar
• Zheng , M. ; Wang , L. ; Shao , J. ; Zhong , Q. A facile synthesis of α,α′-bis(substituted benzylidene)cycloalkanones catalyzed by bis(p-ethoxyphenyl)telluroxide (BMPTO) under microwave irradiation . Synth. Commun. 1997 , 27 , 351 – 354 .
   Web of Science ®Google Scholar
• Iranpoor , N. ; Kazemi , F. RuCl3-catalyzed aldol condensation of aldehydes and ketones . Tetrahedron 1998 , 54 , 9475 – 9480 .
   Web of Science ®Google Scholar
• Bao , W. L. ; Zhang , Y. M. Convenient preparation of α,α′-bis(substituted-benzylidene) cycloalkanones promoted by SmI3 . Chin. Org. Chem. 1998 , 18 , 272 – 274 .
   Google Scholar
• Nakano , T. ; Irfune , 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. ; Zeynizadeh , B. ; Aghapour , B. Aldol condensation of cycloalkanones with aromatic aldehydes catalyzed with TiCl3(OTf). J. Chem. Res. 1999, 554–555.
   Google Scholar
• Yaday , J. S. ; Reddy , B. V. S. ; Nagaraju , A. ; Sarma , J. A. R. P. Microwave-assisted synthesis of α,α′-bis(benzylidene)ketones in dry media . Synth. Commun. 2002 , 32 , 893 – 896 .
   Google Scholar
• Zhang , X. Y. ; Fan , X. S. ; Niu , H. Y. ; Wang , J. J. Ionic liquid as a recyclable medium for the green preparation of α,α′-bis(substituted benzylidene)cycloalkanones catalyzed by FeCl3·6H2O . Green Chem. 2003 , 5 , 267 – 269 .
   Web of Science ®Google Scholar
• Huang , D. F. ; Wang , J. X. ; Hu , Y. L. A new solvent-free synthesis of α,α′-dibenzylidenecycloalkanones from acetals with cycloalkanones under microwave irradiation . Chin. Chem. Lett. 2003 , 14 , 333 – 334 .
   Web of Science ®Google Scholar
• Deng , G. ; Ren , T. Indium trichloride catalyzes aldol condensations of aldehydes and ketones . Synth. Commun. 2003 , 33 , 2995 – 3001 .
   Web of Science ®Google Scholar
• Sabitha , G. ; Reddy , G. S. K. ; Reddy , K. B. ; Yaday , J. S. Iodotrimethylsilane-mediated cross-aldol condensation: A facile synthesis of α,α′-bis(substituted-benzylidene)cycloalkanones . Synthesis 2004 , 263 – 266 .
   Google Scholar
• Wang , L. ; Sheng , J. ; Tian , H. ; Han , J. ; Fan , Z. ; Qian , C. A convenient synthesis of α,α′-bis(substituted-benzylidene)cycloalkanones catalyzed by Yb(OTf)3 under solvent-free conditions . Synthesis 2004 , 3060 – 3064 .
   Google Scholar
• Biswanath , D. ; Ponnaboina , T. ; Ibram , M. ; Kongara , R. R. Convenient and facile cross-aldol condensation catalyzed by molecular iodine: An efficient synthesis of α,α′-bis(substituted-benzylidene)cycloalkanones . J. Mol. Cat. A: Chem. 2006 , 247 , 182 – 185 .
   Google Scholar
• Mohammad , A. B. ; Gholam , H. M. ; Saeed , J. ; Hassan , H. 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 . Cat. Commun. 2007 , 8 , 2228 – 2230 .
   Google Scholar
• Rahman , M. A. F. M. ; Jeong , B.-S. ; Kim , D. H. ; Park , J. K. ; Lee , E. S. ; Jahng , Y. A facile synthesis of α,α′-bis(substituted-benzylidene)cycloalkanones and substituted-benzylidene heteroaromatics: Utility of NaOAc as catalyst for aldol-type reaction . Tetrahedron 2007 , 63 , 2426 – 2431 .
   Web of Science ®Google Scholar
• An , L. T. ; Zou , J. P. ; Zhang , L. L. Polymer-supported sulphonic acid–catalyzed cross-aldol condensation: An expeditious synthesis of α,α′-bis(substituted-benzylidene)cycloalkanones . Catal. Commun. 2008 , 9 , 349 – 354 .
   Web of Science ®Google Scholar
• Parvulescu , V. I. ; Hardacre , C. Catalysis in ionic liquids . Chem. Rev. 2007 , 107 , 2615 – 2665 .
   PubMed Web of Science ®Google Scholar
• Dupont , J. ; de Souza , R. F. ; Suarez , P. A. Z. Ionic liquid (molten salt) phase organometallic catalysis . Chem. Rev. 2002 , 102 , 3667 – 3692 .
   PubMed Web of Science ®Google Scholar
• Wasserscheid , P. ; Welton , T. Ionic Liquids in Synthesis ; Wiley-VCH : New York , 2002 .
   Google Scholar
• Welton , T. Room-temperature ionic liquids solvents for synthesis and catalysis . Chem. Rev. 1999 , 8 , 2071 – 2084 .
   Google Scholar
• Wasserschied , P. ; Keim , W. Ionic liquids—New “solutions” for transition metal catalysis . Angew. Chem. Int. Ed. 2000 , 39 , 3772 – 3789 .
   PubMed Web of Science ®Google Scholar
• Davis , J. H. ; Fox , P. A. From curiosities to commodities: Ionic liquids begin the transition . Chem. Commun. 2003 , 11 , 1209 – 1212 .
   PubMed Web of Science ®Google Scholar