Facile and Green Syntheses of 2-(N-Methylindole-3-carbonyl)-3-(N-methylpyrrol-2-yl)acrylonitriles and a Study of Their Antimicrobial Activities

REFERENCES

• Jones , G. The Knovenagel Condensation Reaction in Organic Reactions ; Wiley : New York , 1967 ; vol. 15 , pp. 204 – 599 .
   Google Scholar
• Knoevenagel , E. Condensation von malonsaure mit aromatiachen durch ammoniak und amine . Berichte 1898 , 31 , 2585 – 2596 .
   Google Scholar
• Tietze , L. ; Beifuos , V. In Comprehensive Organic Synthesis ; B. M. Trost , I. Fleming , and C. H. Heathcock (Eds.); Pergamon : Oxford , 1991 ; vol. 2 , pp. 341 – 392 .
   Google Scholar
• Freeman , F. An efficient synthesis of 2-thienylmethylenemalononitrile . Chem. Rev. 1981 , 80 , 329 – 350 .
   Web of Science ®Google Scholar
• Tietze , L. F. ; Saling , P. Enantioselective intramolecular hetero-Diels–Alder reactions of 1-oxa-1, 3-butadienes with a new chiral Lewis acid . Synlett. 1992 , 23 , 281 – 282 .
   Google Scholar
• Tietze , L. F. Domino reactions in organic synthesis . Chem. Rev. 1996 , 96 , 115 – 136 .
   PubMed Web of Science ®Google Scholar
• Cragoe , E. J. ; Robb , C. M. ; Spragne , J. M. The synthesis of a disubstituted succinic acids from ethyl alkylidene cyanoacetate . J. Org. Chem. 1950 , 15 , 381 – 390 .
   Google Scholar
• Bastus , J. B. The reaction of diazomethane with double bonds, a stepwise and improved Buchner–Curtius–Schlotterbeck reaction . Tetrahedron Lett. 1963 , 4 , 955 – 958 .
   Google Scholar
• Narsaiah , A. V. ; Basak , A. K. ; Visali , B. ; Nagaiah , K. An ecofriendly synthesis of electrophilic alkenes catalyzed by dimethylaminopyridine under solvent-free conditions . Synth. Commun. 2004 , 34 , 2893 – 2901 .
   Web of Science ®Google Scholar
• Rodriguez , I. ; Iborra , S. ; Corma , A. ; Rey , F. ; Jorda , J. L. MCM-41-quaternary organic tetraalkylammonium hydroxide composites as strong and stable Bronsted base catalysts . Chem. Commun. 1999 , 35 , 593 – 594 .
   Web of Science ®Google Scholar
• Rao , P. S. ; Ratnam , R. V. Zinc chloride as a new catalyst for Knoevenagel condensation . Tetrahedron Lett. 1991 , 32 , 5821 – 5822 .
   Web of Science ®Google Scholar
• Narsaiah , A. V. ; Nagaiah , K. An efficient Knoevenagel condensation catalyzed by LaCl3 · 7H2O in heterogenous medium . Synth. Commun. 2003 , 33 , 3825 – 3832 .
   Web of Science ®Google Scholar
• Texier-Boullet , F. ; Foucod , A. Knoevenagel condensation catalyzed by aluminum oxide . Tetrahedron Lett. 1982 , 23 , 4927 – 4928 .
   Web of Science ®Google Scholar
• Cabello , J. A. ; Campelo , J. M. ; Garcia , A. ; Luna , D. ; Marians , J. M. Knoevenagel condensation in the heterogenous phase using AlPO4-Al2O3 as a new catalyst . J. Org. Chem. 1984 , 49 , 5195 – 5197 .
   Web of Science ®Google Scholar
• Wang , Q. L. ; Ma , Y. ; Zuo , B. Knoevenagel condensation catalyzed by USY zeolite . Synth. Commun. 1997 , 27 , 4107 – 4110 .
   Web of Science ®Google Scholar
• Villemin , D. ; Martin , B. Dry condensation of creatinine with aldehydes under focused microwave irradiation . Synth. Commun. 1995 , 25 , 3135 – 3140 .
   Web of Science ®Google Scholar
• Lonpy , A. ; Song , S. J. ; Sohn , S. M. ; Lee , Y. M. ; Kwon , T. W. Solvent-free bentonite-catalyzed condensation of malonic acid aromatic aldehydes under microwave irradiation. J. Chem. Soc., Perkin Trans. 1 2001, 1220–1222.
   Google Scholar
• Bogdal , D. Fast synthesis by Knoevenagel condensation under microwave irradiation . J. Chem. Res., Synop. 1998 , 468 – 469 .
   Web of Science ®Google Scholar
• Li , J. T. ; Chen , G. F. ; Wang , S. X. ; He , L. ; Li , T. S. Synthesis of arylmethylene malononitrile catalyzed by KF-Al2O3 under ultrasound . Aus. J. Chem. 2005 , 58 , 231 – 233 .
   Web of Science ®Google Scholar
• McNutly , J. ; Steere , J. A. ; Wolf , S. The ultrasound-promoted Knoevenagel condensation of aromatic aldehydes . Tetrahedron Lett. 1998 , 39 , 8013 – 8016 .
   Web of Science ®Google Scholar
• Ren , Z. J. ; Cao , W. G. ; Tong , W. Q. The Knoevenagel condensation reaction of aromatic aldehydes with malononitrile by grinding in the absence of solvent and catalyst . Synth. Commun. 2002 , 32 , 3475 – 3479 .
   Web of Science ®Google Scholar
• Su , C. ; Chen , Z. C. ; Zheng , Q. G. Organic reactions in ionic liquids: Knoevenagel condensation catalyzed by ethylenediammonium diacetate . Synthesis 2003 , 4 , 555 – 559 .
   Google Scholar
• Darvatkar , N. B. ; Deorukhar , A. R. ; Bhilare , S. V. ; Salunkhe , M. M. Ionic liquid–mediated Knoevenagel condensation of meldrum's acid and aldehydes . Synth. Commun. 2006 , 36 , 3043 – 3057 .
   Web of Science ®Google Scholar
• Hu , Y. ; Chen , J. ; Le , A.-G. ; Zheng , Q.-G. Organic reactions in ionic liquids: Ionic liquids ethyl ammonium nitrate–promoted Knoevenagel condensation of aromatic aldehydes with active methylene compounds . Synth. Commun. 2005 , 35 , 739 – 744 .
   Web of Science ®Google Scholar
• Khan , F. A. ; Dash , J. ; Satapahty , R. ; Upahyay , S. K. Hydrotalcite catalysis in ionic liquid medium: A recyclable reaction system for heterogeneous Knoevenagel and nitroaldol condensation . Tetrahedron Lett. 2004 , 45 , 3055 – 3058 .
   Web of Science ®Google Scholar
• Harjani , J. R. ; Nara , S. J. ; Salunkhe , M. M. Lewis acidic ionic liquids for the synthesis of electrophilic alkenes via the Knoevenagel condensation . Tetrahedron Lett. 2002 , 43 , 1127 – 1130 .
   Web of Science ®Google Scholar
• Wang , S. ; Ren , Z. ; Cao , W. ; Tong . The Knoevenagel condensation of aromatic aldehydes with malononitrile or ethyl cyanoacetate in the presence of CTMAB in water . Synth. Commun. 2001 , 31 , 673 – 677 .
   Web of Science ®Google Scholar
• Jin , T. S. ; Wang , X. ; Liu , L. B. ; Li , T. S. Clean synthesis of ethyl α-cyano cinnamates catalysed by hexadecyltrimethyl ammonium bromide in aqueous media . J. Chem. Res. 2006 , 6 , 346 – 347 .
   Google Scholar
• Jin , T. S. ; Zhang , J. S. ; Wang , A. Q. ; Li , T. S. An efficient and environmentally friendly procedure for the synthesis of arylmethylenemalononitrile catalyzed by strong base anion-exchange resin in water . Synth. Commun. 2004 , 34 , 2611 – 2616 .
   Web of Science ®Google Scholar
• Bigi , F. ; Carloni , S. ; Ferrari , L. ; Maggi , R. ; Mazzacani , A. ; Sartori , G. Clean synthesis in water, part 2: Uncatalyzed condensation reaction of Meldrum's acid and aldehydes . Tetrahedron Lett. 2001 , 42 , 5203 – 5205 .
   Web of Science ®Google Scholar
• Sakthivel , K. ; Notz , W. ; Bui , T. ; Barbas , C. F. Amino acid–catalyzed direct asymmetric aldol reactions: A bio-organic approach to catalytic asymmetric carbon–carbon bond-forming reactions . J. Am. Chem. Soc. 2001 , 123 , 5260 – 5267 .
   PubMed Web of Science ®Google Scholar
• Groger , H. ; Wilken , J. The application of L-proline as an enzymemimic and further new asymmetric syntheses using small organic molecules as chiral catalysts . Angew. Chem., Int. Ed. Engl. 2001 , 40 , 529 – 532 .
   PubMed Web of Science ®Google Scholar
• Cardillo , G. ; Fabbroni , S. ; Gentilucci , L. ; Gianotti , M. ; Tolomelli , A. A straight forward method for the synthesis of alkylidene and arylidene malonates through proline-catalyzed Knoevenagel condensation . Synth. Commun. 2003 , 33 , 1587 – 1594 .
   Web of Science ®Google Scholar
• Brem , G. ; Loupy , A. ; Sansoulet , J. Polythylene glycols as oligomeric host solvents: Application to oxidation and reduction reactions . Israel J. Chem. 1985 , 26 , 291 – 299 .
   Web of Science ®Google Scholar
• Wang , M. ; Chang , K. R. Effects of polyethyleneglycol 400 on the allylation of phenoxide in a homogenous phase . Ind. Eng. Chem. Res. 1990 , 29 ( 1 ), 40 – 45 .
   Web of Science ®Google Scholar
• Cao , Y. Q. ; Chen , B. H. Cyanidation of halogen compounds and esters catalyzed by PEG-400 without solvent. Synth. Commun. 2001, 31, 2202–2206.
   Web of Science ®Google Scholar
• Cao , Y. Q. ; Pei , B. G. Etherification of phenols catalyzed by solid–liquid phase transfer catalyst PEG-400 without solvent . Synth. Commun. 2000 , 30 , 1759 – 1766 .
   Web of Science ®Google Scholar
• Frankel , S. ; Reitman , S. ; Sonnenwirth , A. C. Gradwol's Clinical Laboratory Methods and Diagnosis, , 7th ed. ; Mosby: St. Louis , 1970 ; vol. 2 , pp. 1406 – 1459 .
   Google Scholar
• Maron , D. M. ; Ames , B. N. Revised methods for the salmonella mutagenicity test . Mutation Res. 1983 , 113 , 173 – 215 .
   PubMed Web of Science ®Google Scholar
• Kilic , A. ; Baysallar , M. ; Besirbellioglu , B. ; Salih , B. ; Sorkun , K. ; Tanyuksel , M. In vitro antimicrobial activity of propolis against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus faecium . Ann. Microbiol . 2005 , 55 , 113 – 118 .
   Web of Science ®Google Scholar