An efficient and practical synthesis of 1-aryl-1H,3H-thiazolo[3,4-a]benzimidazole using silica-supported sodium hydrogen sulfate as a heterogeneous catalyst

References

• Yildiz-Oren I , Yalcin I , Aki-Sener E , Carturk N . Eur. J. Med. Chem. Synthesis and structure-activity relationships of new antimicrobial active multisubstituted benzazole derivatives . 2004 ; 39 : 291 – 298 .
   Google Scholar
• Yamato M . J. Pharm. Soc. Jpn. Study on the Development of Biological-Active Compounds after the Model of Natural Products. 1992 ; 112 : 81 – 99 .
   Google Scholar
• Benazzouz A , Boraud T , Dubedat P , Boireu A , Stutzmann JM , Gross C . Eur. J. Pharmacol. Riluzole prevents MPTP-induced parkinsonism in the rhesus monkey: a pilot study. 1995 ; 284 : 299 – 307 .
   Google Scholar
• Kumar D , Jacob MR , Reynolds MB , Kerwin SM . Bioorg. Med. Chem . 2002 ; 10 : 3997 – 4004 . doi: 10.1016/S0968-0896(02)00327-9
   PubMed Web of Science ®Google Scholar
• Evans DA , Sacks CE , Kleschick WA , Taber TR . J. Am. Chem. Soc. Polyether Antibiotics Synthesis. The Total Synthesis and Absolute Configuration of the Ionophore A-23187 . 1979 ; 101 : 6789 – 6791 .
   Google Scholar
• So YH , Heeschem JP . J. Org. Chem. Mechanism of Polyphosphoric Acid and Phosphorus Pentoxide–Methanesulfonic Acid as Synthetic Reagents for Benzoxazole Formation . 1997 ; 62 : 3552 – 3561 .
   Google Scholar
• Villemin D , Hammadi M , Martin B . Synth. Commun. Clay Catalysis: Condensation of Orthoesters with O-Substituted Aminoaromatics into Heterocycles . 1996 ; 26 : 2895 – 2899 .
   Google Scholar
• Terashima M , Ishii M . Synthesis. A facile synthesis of 2-substituted benzoxazoles 1982 ; 484 .
   Google Scholar
• Hein DW , Alheim RJ , Leavitt J . J. Am. Chem. Soc. The Use of Polyphosphoric Acid in the Synthesis of 2-Aryl- and 2-Alkyl-substituted Benzimidazoles, Benzoxazoles and Benzothiazoles . 1957 ; 79 : 427 – 429 .
   Google Scholar
• Salehi P , Dabiri M , Zolfigol MA , Otokesh S , Baghbanzadeh M . Tetrahedron Lett. Selective synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles in water at ambient temperature . 2006 ; 47 : 2557 – 2560 .
   Google Scholar
• Chimirri A , Monforte P , Musumeci L , Rao A , Zappala M , Monforte A . Arch. Pharm. Synthesis and antitumour activity of 1H,3H-thiazolo[3,4-a]benzimidazole derivatives . 2001 ; 334 : 203 – 208 .
   Google Scholar
• Rao A , Chimirri A , Ferro S , Monforte A , Monforte P , Zappala M . Arkivoc. Microwave-assisted synthesis of benzimidazole and thiazolidinone derivatives as HIV-1 RT inhibitors . 2004 ; V : 147 – 155 .
   Google Scholar
• Yadav AK , Kumar M , Yadav T , Jain R . Tetrahedron Lett. An ionic liquid mediated one-pot synthesis of substituted thiazolidinones and benzimidazoles . 2009 ; 50 : 5031 – 5034 .
   Google Scholar
• Bärfacker L , Buss C , Hollmann C , Kitsos-Rzychon BE , Kranemann CL , Rische T , Roggenbuck R , Eilbracht P , Schimdt A . Chem. Rev. Tandem Reaction Sequences under Hydroformylation Conditions: New Synthetic Applications of Transition Metal Catalysis . 1999 ; 99 : 3329 – 3366 .
   Google Scholar
• Montgomery J . Acc. Chem. Res . 2000 ; 33 : 467 – 473 . doi: 10.1021/ar990095d
   PubMed Web of Science ®Google Scholar
• Domling A , Ugi I . Angew. Chem. Int. Ed. Engl. Multicomponent Reactions with Isocyanides . 2000 ; 39 : 3168 – 3210 .
   PubMed Web of Science ®Google Scholar
• Ramesh C , Ravindranath N , Das B . J. Org. Chem. Simple, Efficient, and Selective Deprotection of Phenolic Methoxymethyl Ethers Using Silica-Supported Sodium Hydrogen Sulfate as a Heterogeneous Catalyst . 2003 ; 68 : 7101 – 7103 .
   Google Scholar
• Das B , Venkateswarlu K , Mahender G , Mahender I . Tetrahedron Lett. A simple and efficient method for α-bromination of carbonyl compounds using N-bromosuccinimide in the presence of silica-supported sodium hydrogen sulfate as a heterogeneous catalyst . 2005 ; 46 : 3041 – 3044 .
   Google Scholar
• Chaskar A , Padalkar V , Phatangare K , Patil K , Bodkhe A , Langi B . Appl. Catal. A: Gen. Heteropoly Acids as a Useful Recyclable Heterogeneous Catalyst for the Facile and Highly Efficient Aza-Cope rearrangement of N-allylanilines . 2009 ; 359 : 84 – 87 .
   Google Scholar
• Phatangare K , Padalkar V , Mhatre D , Patil K , Chaskar A . Synth. Commun . 2009 ; 39 : 4117 – 4121 . doi: 10.1080/00397910902885533
   Web of Science ®Google Scholar
• Gawand P , Deokar H , Langi B , Yadav A , Chaskar A . Synth. Commun . 2009 ; 39 : 4171 – 4179 . doi: 10.1080/00397910902885541
   Web of Science ®Google Scholar
• Breton GW . J. Org. Chem. Selective Monoacetylation of Unsymmetrical Diols Catalyzed by Silica Gel-Supported Sodium Hydrogen Sulfate . 1997 ; 62 : 8952 .
   Google Scholar