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Beilstein J. Org. Chem. 2012, 8, 259–265, doi:10.3762/bjoc.8.27
Graphical Abstract
Scheme 1: Retrosynthetic analysis of the designed target molecules.
Scheme 2: Synthetic routes for 4-chlorophenyl tribromomethyl sulfone (1).
Scheme 3: Halogenation/nitration sequence for 4-halogenphenyl methyl sulfones 4 and 4'.
Scheme 4: SNAr transformations of sulfone 6.
Scheme 5: Preparation of phenylhydrazones 8a–8l.
Scheme 6: Products of the nitro group reduction of sulfone 7a.
Scheme 7: Synthesis of benzimidazole derivatives 11a–11g.
Scheme 8: Preparation and further transformation of 2-mercaptobenzimidazole 11h.