Water-Mediated Synthesis of 2-Substituted Benzimidazoles by Boric Acid and Glycerol

A very simple, mild, and highly efficient green catalyst has been developed for the synthesis of 2-substituted benzimidazoles by treatment of substituted ortho-phenylenediamines and aldehydes in water at 80°C in the presence of boric acid (5 mol-%) and glycerol (0.05 mL). This methodology has been standardized on 55 substrates, and nine new compounds have been synthesized.

[1]  C. Mukhopadhyay,et al.  PEG-mediated catalyst-free expeditious synthesis of 2-substituted benzimidazoles and bis-benzimidazoles under solvent-less conditions , 2008 .

[2]  S. Boukhris,et al.  Easy access to triazoles, triazolopyrimidines, benzimidazoles and imidazoles from imidates , 2008 .

[3]  F. Bamoharram,et al.  HETEROPOLYACIDS AS HETEROGENEOUS AND RECYCLABLE CATALYSTS FOR THE SYNTHESIS OF BENZIMIDAZOLES , 2008 .

[4]  K. Sumoto,et al.  IMPROVED CONVENIENT AND ENVIRONMENTALLY BENIGN SYNTHESIS OF BIOLOGICAL ACTIVE BENZIMIDAZOLES USING ACTIVATED CARBON AND MOLECULAR OXYGEN , 2008 .

[5]  Huiqiang Ma,et al.  A simple and efficient method for synthesis of benzimidazoles using FeBr3 or Fe(NO3)3・9H2O as catalyst , 2007 .

[6]  Yong-mei Wang,et al.  An expeditious synthesis of benzimidazole derivatives catalyzed by Lewis acids , 2007 .

[7]  Wang Yulu,et al.  p-TsOH Catalyzed synthesis of 2-arylsubstituted benzimidazoles , 2007 .

[8]  K. Bahrami,et al.  A Simple and Efficient One-Pot Synthesis of 2-Substituted Benzimidazoles , 2007 .

[9]  C. Mukhopadhyay,et al.  Dowex 50W in aqueous medium : Highly efficient biginelli condensation procedure for the synthesis of 4-aryl-3,4-dihydropyrimidones , 2007 .

[10]  Huiqiang Ma,et al.  Selective Synthesis of 2-Aryl-1-arylmethyl-1H-1,3-benzimidazoles Promoted by Ionic Liquid , 2007 .

[11]  B. Das,et al.  Efficient (bromodimethyl)sulfonium bromide mediated synthesis of benzimidazoles , 2007 .

[12]  R. Villalobos-Molina,et al.  Design, microwave-assisted synthesis, and spasmolytic activity of 2-(alkyloxyaryl)-1H-benzimidazole derivatives as constrained stilbene bioisosteres. , 2006, Bioorganic & medicinal chemistry letters.

[13]  王玉炉,et al.  A simple KHSO4 promoted synthesis of 2-arylsubstituted benzimidazoles by oxidative condensation of aldehydes with o-phenylenediamine , 2006 .

[14]  D. Sauer,et al.  A simple and efficient one step synthesis of benzoxazoles and benzimidazoles from carboxylic acids , 2006 .

[15]  P. Seeberger,et al.  Application of Sulfamic Acid as an Eco-friendly Catalyst in an Expedient Synthesis of Benzimidazoles , 2006 .

[16]  R. Gibbs,et al.  A convenient one-pot synthesis of 2-substituted benzimidazoles , 2006 .

[17]  P. Gogoi,et al.  An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon–nitrogen bonds in water , 2006 .

[18]  Lihu Yang,et al.  A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant , 2005 .

[19]  T. Itoh,et al.  Synthesis of 2-Arylbenzothiazoles and Imidazoles Using Scandium Triflate as a Catalyst for Both a Ring Closing and an Oxidation Steps , 2004 .

[20]  B. Kim,et al.  Indium-mediated Reductive Inter-molecular Coupling Reaction of 2-Nitroaniline with Aromatic Aldehydes to Benzimidazoles , 2004 .

[21]  T. Itoh,et al.  Synthesis of 2-Substituted Benzimidazoles by Reaction of o-Phenylenediamine with Aldehydes in the Presence of Sc(OTf)3 , 2003 .

[22]  J. Gallucci,et al.  Intramolecular aromatic nucleophilic substitution of the benzimidazole-activated nitro group. , 2003, Organic letters.

[23]  J. Clyburne,et al.  Compounds of chromium(VI): The pyridine chromic anhydride complex, benzimidazolinium dichromate, and three 2-alkyl-1H-benzimida -zolinium dichromates , 2003 .

[24]  Douglas A. Horton,et al.  The combinatorial synthesis of bicyclic privileged structures or privileged substructures. , 2003, Chemical reviews.

[25]  K. Janda,et al.  Traceless solid-phase synthesis of 5-benzoylbenzimidazoles , 2001 .

[26]  C. Hulme,et al.  Two-step solution-phase synthesis of novel benzimidazoles utilizing a UDC (Ugi/de-Boc/cyclize) strategy , 2001 .

[27]  G. Parkinson,et al.  A new class of symmetric bisbenzimidazole-based DNA minor groove-binding agents showing antitumor activity. , 2001, Journal of medicinal chemistry.

[28]  J. Girardet,et al.  Design, synthesis, and antiviral activity of alpha-nucleosides: D- and L-isomers of lyxofuranosyl- and (5-deoxylyxofuranosyl)benzimidazoles. , 1998, Journal of medicinal chemistry.

[29]  L. Kucera,et al.  Design, synthesis, and antiviral evaluations of 1-(substituted benzyl)-2-substituted-5,6-dichlorobenzimidazoles as nonnucleoside analogues of 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole. , 1998, Journal of medicinal chemistry.

[30]  P. Grieco Organic synthesis in water , 1998 .

[31]  W. Wilson,et al.  Synthesis of mono‐cationic and dicationic analogs of hoechst 33258 , 1996 .

[32]  E. Bouwman,et al.  Model systems for type I copper proteins: structures of copper coordination compounds with thioether and azole-containing ligands , 1990 .

[33]  P. Little,et al.  Inhibition of rat hepatic microsomal aminopyrine N-demethylase activity by benzimidazole derivatives. Quantitative structure-activity relationships. , 1982, Journal of medicinal chemistry.

[34]  R. Tidwell,et al.  Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole-like ring. Inhibitors of arginine-specific esteroproteases. , 1978, Journal of medicinal chemistry.

[35]  P. Sehgal,et al.  Halobenzimidazole ribosides and RNA synthesis of cells and viruses. , 1978, Advances in virus research.

[36]  L. Zaika,et al.  1,2,3-benzotriazines. II. Reactions of benzimidazo[1,2-c][1,2,3]benzotriazines and naphth[1′,2′(2′,1′):4,5]imidazo[1,2-c][1,2,3]benzotriazine† , 1966 .

[37]  L. Zaika,et al.  1,2,3‐benzotriazines. I. The synthesis of some benzimidazo [1,2‐c][1,2,3]‐benzotriazines and naphth[1′,2,(2′,1′):4,5]imidazo[1,2‐c][1,2,3]benzotriazine , 1966 .

[38]  R. C. D. Selms Benzimidazoles. II. Synthesis of N-Heterocyclic Ring Systems Containing 1,2-Fused Benzimidazole Moieties , 1962 .

[39]  H. Fischer,et al.  Zur Darstellung der Benzimidazole , 1952 .