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Note | Regular issue | Vol 75, No. 1, 2008, pp.165-171
Published online, 20th September, 2007
DOI: 10.3987/COM-07-11148
Sulfuric Acid Mediated Heterocyclization of ortho-Cyanomethylnitroarenes to Benzo[c]isoxazoles and Fused Benzo[c]isoxazoles

Mehdi Bakavoli,* Mehdi Pordel, Mohammad Rahimizadeh, Pooneh Jahandari, and Esmaeel Rezaei Seresht

*Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, Mashhad, 91775-1436, Iran

Abstract

The vicarious nucleophilic substitution of hydrogen (VNS) is used as the key step to convert substituted 5-nitrobenzimidazoles 1a-b into their ortho-cyanomethyl derivatives 2a-b. Conc. sulfuric acid mediated heterocyclization of these intermediates gave the novel 3H-imidazo[4’,5’:3,4]benzo[c]isoxazole-8-carboxamides 3a-b. To generalize this synthetic strategy for benzo[c]isoxazoles syntheses, the VNS products of para-substituted nitrobenzene 4a-d were successfully converted to the new benzo[c]isoxazoles derivatives 5a-d.