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Synthesis 2000; 2000(10): 1380-1390
DOI: 10.1055/s-2000-7111
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Synthetic Utility of Catalytic Fe(III)/Fe(II) Redox Cycling Towards Fused Heterocycles: A Facile Access to Substituted Benzimidazole, Bisbenzimidazole and Imidazopyridine Derivatives

Malvinder P. Singh* , Sanjita Sasmal, Wei Lu, Manashi N. Chatterjee
  • *Department of Chemistry, 110 Science Place, University of Saskatchewan, Saskatoon, Sask. S7N 5C9, Canada; Fax + 1(306) 9 66 47 30; E-mail: singh@sask.usask.ca
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Publication Date:
31 December 2000 (online)

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A catalytic Fe(III)/Fe(II) redox cycling approach has been examined and applied towards synthesis of a wide range of benzimidazole, bis-benzimidazole and imidazopyridine derivatives from oxidative coupling of aromatic ortho-diamines with aromatic as well as heterocyclic aldehydes bearing different types of substituents. This versatile and convenient method has further proven to be particularly useful in expeditiously affording a number of novel bis-benzimidazole class of Hoechst 33 258 analogs towards potential development as fluorescent nucleic acid binding probes. Successful preparation and characterization of a diverse set of thirty different compounds is presented here.

benzimidazoles - bis-benzimidazoles - imidazopyridines - catalytic redox-cycling - fluorescent probes - heterocycles - Schiff bases