Synthesis of Benzimidazoles and Benzoxazoles Using Palladium Bis(2,2,6,6-tetramethyl-3,5-heptanedionate) as a Novel Catalyst

REFERENCES

• Preston , P. N. Benzimidazoles and Congeneric Tri-cyclic Compounds, Parts 1 and 2 ; Wiley : New York , 1981 ; vol. 40 , and references therein.
   Google Scholar
• Preston , P. N. Synthesis reactions and spectroscopic properties of benzimidazoles. Chem. Rev. 1974, 74, 279.
   Web of Science ®Google Scholar
• Cadogan , J. I. G. ; Marshall , R. ; Smith , D. M. ; Todd , M. J. Reduction of nitro- and nitroso-compounds by tervalent phosphorus reagents, part VIII: Syntheses of benzimidazoles and anthranils . J. Chem. Soc. C 1970 , 2441 .
   Google Scholar
• Tollari , S. ; Cenini , S. ; Crotti , C. ; Gianella , E. Synthesis of heterocycles via palladium-catalyzed carbonylation of ortho-substituted organic nitro compounds in relatively mild conditions . J. Mol. Catal. 1994 , 87 , 203 .
   Google Scholar
• Nishiyama , Y. ; Fujimoto , M. ; Sonoda , N. A new method for the synthesis of 2-aryl-1H-benzimidazoles: Selenium-catalyzed reductive N-heterocyclization of benzylidene(2-nitroaryl)amines with carbon monoxide . Synlett 2006 , 1 , 109 .
   Google Scholar
• Dohle , W. ; Staubitz , A. ; Knochel , P. Mild synthesis of polyfunctional benzimidazoles and indoles by the reduction of functionalized nitroarenes with phenylmagnesium chloride . Chem. Eur. J. 2003 , 9 , 5323 .
   PubMedGoogle Scholar
• Yang , D. ; Fokas , D. ; Li , J. ; Yu , L. ; Baldino , C. M. A versatile method for the synthesis of benzimidazoles from o-nitroanilines and aldehydes in one step via a reductive cyclization . Synthesis 2005 , 1 , 47 .
   Google Scholar
• Surpur , M. P. ; Singh , P. R. ; Patil , S. B. ; Samant , S. D. One-pot synthesis of benzimidazoles from o-nitroanilines under microwaves via a reductive cyclization . Synth. Commun. 2007 , 37 , 1375 .
   Web of Science ®Google Scholar
• Hornberger , K. R. ; Adjabeng , G. M. ; Dickson , H. D. ; Dawis-Ward , R. G. A mild, one-pot synthesis of disubstituted benzimidazoles from 2-nitroanilines . Tetrahedron Lett. 2006 , 47 , 5359 .
   Web of Science ®Google Scholar
• Guo , D. ; He , H. ; Xu , J. ; Jiang , H. Efficient iron catalyzed N-arylation of aryl halides with amines . Org. Lett. 2008 , 10 , 4513 – 4516 .
   PubMed Web of Science ®Google Scholar
• Tararov , V. I. ; Kadyrov , R. ; Riermeier , T. H. ; Börner , A. On the reductive amination of aldehydes and ketones catalyzed by homogeneous Rh(I) complexes . Chem. Commun. 2000 , 1867 .
   Web of Science ®Google Scholar
• Bhanushali , M. J. ; Nandurkar , N. S. ; Bhor , M. D. ; Bhanage , B. M. Palladium/1,2-bis(diphenylphosphino)ethane catalysed amination of aryl halides with aliphatic/aromatic amines . J. Mol. Catal. A: Chem. 2006 , 259 , 46 , and references therein .
   Google Scholar
• Vanier , G. S. Simple and efficient microwave-assisted hydrogenation reactions at moderate temperature and pressure . Synlett 2007 , 1 , 131 .
   Google Scholar
• Chapman , N. ; Conway , B. ; O'Grady , F. ; Wall , M. D. A convenient method to aniline compounds using microwave-assisted transfer hydrogenation . Synlett 2006 , 7 , 1043 .
   Google Scholar
• Kumar , R. ; Selvam , C. ; Kaur , G. ; Chakraborti , A. K. Microwave-assisted direct synthesis of 2-substituted benzoxazoles from carboxylic acids under catalyst and solvent-free conditions . Synlett 2005 , 9 , 1401 , and references therein .
   Google Scholar
• Evindar , G. ; Batey , R. A. Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides . J. Org. Chem. 2006 , 71 , 1802 .
   PubMed Web of Science ®Google Scholar
• Kumar , D. ; Jacob , M. R. ; Reynolds , M. B. ; Kerwin , S. M. Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1 . Bioorg. Med. Chem. 2002 , 10 , 3997 .
   PubMed Web of Science ®Google Scholar
• Baltork , I. M. ; Khosropour , A. R. ; Hojati , S. F. ZrOCl2·8H2O as an efficient, environmentally friendly, and reusable catalyst for synthesis of benzoxazoles, benzothiazoles, benzimidazoles, and oxazolo[4,5-b]pyridines under solvent-free conditions . Catal. Commun. 2007 , 8 , 1865 .
   Web of Science ®Google Scholar