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Synthesis of 1-alkoxy-2-alkyl-benzimidazoles from 2-nitroanilines via tandem N-alkylation-cyclization-O-alkylation

1995; Elsevier BV; Volume: 51; Issue: 14 Linguagem: Inglês

10.1016/0040-4020(95)00127-t

1464-5416

John M. Gardiner, Colin R. Loyns, Carl H. Schwalbe, G. C. Barrett, Philip R. Lowe,

Synthesis and Characterization of Heterocyclic Compounds

Substituted 2-nitroanilines react with benzylic, allyl and alkyl halides to give 2-aryl-1-benzyloxy-, 1-allyloxy-2-vinyl- and 1-alkoxy-2-alkyl-benzimidazoles, in a one-pot cascade process involving 1-alkylation-cyclization-O-alkylation. 2-Aryl-1-benzyloxy- and 1-allyloxy-2-vinyl- derivatives are obtained in high yields (79–98%), while with simple alkyl halides, yields of the benzimidazoles are substrate dependent. An X-ray crystal structure of 2,4-dimethyl-1-ethoxybenzimidazole is presented.