Sulfuric acid mediated heterocyclization of ortho-cyanomethylnitroarenes to benzo[c]isoxazoles and fused benzo[c]isoxazoles.

[摘要]：The vicarious nucleophilic substitution of hydrogen (VNS) is used as the key step to convert 1-benzyl- and 1-methyl-5-nitrobenzimidazole into the resp. 4-cyanomethyl derivs. Conc. H2SO4-mediated heterocyclization of these intermediates gave novel 3H-imidazo[4',5':3,4]benzo[c]isoxazole-8-carboxamides I (R = Bn, Me). To generalize this synthetic strategy for benzo[c]isoxazole syntheses, the VNS products of 5-substituted 2-nitrobenzeneacetonitriles were successfully converted to new benzo[c]isoxazole derivs.

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