Na₂S₂O₄: A Versatile Reagent for the One-Pot Synthesis of 2-Aryl-1H-imidazo[4,5-c]pyridines from 4-Amino-3-nitropyridine and Aldehydes via Reductive Cyclization

REFERENCES

• Fellenius , E. ; Berglindh , T. ; Sachs , G. ; Olbe , L. ; Elander , B. ; Sjostrand , S. E. ; Wallmark , B. Substituted benzimidazoles inhibit gastric acid secretion by blocking (H+ + K+) ATP ase . Nature 1981 , 290 , 159 – 161 .
   PubMed Web of Science ®Google Scholar
• Emery , V. C. ; Hassan-Walker , A. F. Focus on new drugs in development against human cytomegalovirus . Drugs 2002 , 62 , 1853 – 1858 .
   Google Scholar
• Sondhi , S. M. ; Singhal , N. ; Johar , M. ; Reddy , B. S. N. ; Lown , J. W. Heterocyclic compounds as inflammation inhibitors . Curr. Med. Chem. 2002 , 9 , 1045 – 1074 .
   Google Scholar
• Hodgkin , E. E. ; Miller , A. ; Whittaker , M. A partial pharmacopoeia for the platelet activating factor (PAF) receptor . Bioorg. Med. Chem. Lett. 1999 , 29 , 597 – 602 .
   Google Scholar
• Temple , J. C. ; Rose , J. D. ; Comber , R. N. ; Rener , G. A. Synthesis of potential anticancer agents: imidazo [4,5-c]pyridines and imidazo [4,5-b]pyridines . J. Med. Chem. 1987 , 30 , 1746 – 1751 .
   PubMed Web of Science ®Google Scholar
• Cooper , K. ; Fray , M. J. ; Parry , M. J. ; Richardson , K. ; Steele , J. 1,4-Dihydropyridines as antagonist of platelet activating factor, 1: Synthesis and structure–activity relationships of 2-(4-heterocyclyl) phenyl derivatives. J. Med. Chem. 1992, 35, 3115–3129.
   PubMed Web of Science ®Google Scholar
• Sanders , D. B. 3,4-Diaminopyridine (DAP) in the treatment of Lambert–Eaton myasthenic syndrome . Ann. N.Y. Acad. Sci. 1998 , 841 , 811 – 816 .
   PubMed Web of Science ®Google Scholar
• Judge , S. I. V. ; Bever , Jr. , C. T. Potassium channel blockers in multiple sclerosis: Neuronal Kv channels and effects of symptomatic treatment . Pharmacol. Therapeut. 2006 , 111 ( 1 ), 224 – 259 .
   PubMed Web of Science ®Google Scholar
• Doherty , G. D. P. Rodenticidal imidazo-pyridines . US Patent 3,941,882, 1976 ; Chem. Abstr. 1976 , 79 , 14235a .
   Google Scholar
• (a) Montgomery , J. A. ; Hewson , K. 3-Deaza-6-methylthiopurine ribonucleoside . J. Med. Chem. 1966 , 9 , 105 – 107 ; (b) Montgomery , A. ; Salemink , C. A. 1-Deaza-6-methylthiopurine ribonucleoside . J. Med. Chem. 1966 , 9 , 354 – 357 .
   Google Scholar
• Middleton , R. W. ; Wimberley , D. G. Synthesis of imidazo[4,5-b]- and [4,5-c]pyridines . J. Heterocycl. Chem. 1980 , 17 , 1757 – 1760 .
   Web of Science ®Google Scholar
• Jiang , B. Preparation of 2-[(aryl)methyl]sulfinyl-1H-imidazo[4,5-c]pyridine, useful as an antiosteoporotic agent . Org. Process Res. Develop. 1998 , 2 ( 6 ), 425 – 427 .
   Google Scholar
• Preston , P. N. Synthesis, reactions, and spectroscopic properties of benzimidazoles . Chem. Rev. 1974 , 74 , 279 – 314 .
   Web of Science ®Google Scholar
• Singh , M. P. ; Sasmal , S. ; Lu , W. ; Chatterjee , M. N. Synthetic utility of catalytic Fe(III)/Fe(II) redox cycling towards fused heterocycles: A facile access to substituted benzimidazole, bisbenzimidazole, and imidazopyridine derivatives . Synthesis 2000 , 1380 – 390 .
   Web of Science ®Google Scholar
• Katner , A. S. ; Brown , R. F. A novel preparation of thiazolo[5,4-c]pyridines and the synthesis of some imidazo[4,5-c]pyridines and oxazolo[4,5-c]pyridines . J. Heterocycl. Chem. 1990 , 27 , 563 – 566 .
   Web of Science ®Google Scholar
• Mederski , W. W. K. R. ; Pachler , K. G. R. Synthesis and structural assignment of some N-substituted imidazopyridine derivatives . Tetrahedron 1992 , 48 , 10549 – 10558 .
   Google Scholar
• Dubey , P. K. ; Kulkarni , S. M. ; Vinod , K. ; Hemasunder , G. Unambiguous structural assignment of monoanils obtained from 2,3-pyridinediamines . Indian J. Chem. 2004 , 43B , 952 – 956 .
   Google Scholar
• Dubey , P. K. ; Chowdary , K. S. ; Ramesh , B. ; Prasada Reddy , P. V. V. Unambiguous structural assignment of monoanils of 3,4-pyridinediamine via regioselective synthesis . Arkivoc 2008 , 13 , 137 – 144 .
   Google Scholar
• Dubey , P. K. ; Prasada Reddy , P. V. V. ; Srinivas , K. One-pot synthesis of 2-(1-alkyl/aralkyl-1H-benzimidazole-2-yl)-quinoxaline derivatives using molecular iodine . Synth. Commun. 2007 , 37 , 2259 – 2266 .
   Web of Science ®Google Scholar
• Dubey , P. K. ; Prasada Reddy , P. V. V. ; Srinivas , K. Alternate method for the synthesis of N-alkyl/aralkyl-2-(α-hydroxy alkyl/aralkyl)benzimidazoles via regiospecific acetylation . Synth. Commun. 2007 , 37 , 1675 – 1681 .
   Web of Science ®Google Scholar
• Fokas , D. ; Li , J. ; Yu , L. ; Carmen , M. B. A versatile method for the synthesis of benzimidazoles from o-nitro anilines and aldehydes in onestep via a reductive cyclization . Synthesis 2005 , 47 – 56 .
   Google Scholar
• Savarini , P. ; Viscard , G. ; Carpignano , R. ; Borda , A. ; Barni , E. Aminophenyl-X-azolo- pyridines as precursors of heterocyclic azo dyes . J. Heterocycl. Chem. 1989 , 26 , 289 – 292 .
   Google Scholar
• Middleton , R. W. ; Wibberley , D. G. Synthesis of imidazo[4,5-b]- and [4,5-c]pyridines . J. Heterocycl. Chem. 1980 , 17 , 1757 – 1760 .
   Web of Science ®Google Scholar
• Puerstinger , G. ; Paeshuyse , J. ; Herdewijn , P. ; Rozenski , J. ; De Clercq , E. ; Neyts , J. Substituted 5-benzyl-2-phenyl-5H-imidazo[4,5-c]pyridines: A new class of pestivirus inhibitors . Bioorg. Med. Chem. Lett. 2006 , 16 , 5345 – 5349 .
   PubMed Web of Science ®Google Scholar
• Bakke , J. M. ; Riha , J. Synthesis of 3,4-diaminopyridine and imidazo[4,5-c]pyridines by nitration of 4-acylaminopyridines . J. Heterocycl. Chem. 1999 , 36 , 1143 – 1145 .
   Google Scholar
• Berner , H. ; Reinshagen , H. ; Koch , M. A. Antiviral 1,2-(α-hydroxybenzyl)imidazo[4,5-c]- pyridine. J. Med. Chem. 1973, 16, 1296–1298.
   PubMed Web of Science ®Google Scholar
• Chatterjee , S. K. ; Jain , P. C. ; Anand , N. Amino pyridines . Indian J. Chem. 1965 , 3 , 138 – 139 .
   Google Scholar
• Harris , M. G. ; Stewart , R. Amino group acidity in amino pyridines and aminopyrimidines . Can. J. Chem. 1977 , 55 , 3800 .
   Google Scholar