Tetrahedron p. 4101 - 4110 (1995)
Update date:2022-08-05
Topics:
Gardiner, John M.
Loyns, Colin R.
Schwalbe, Carl H.
Barrett, Garry C.
Lowe, Philip R.
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 (79-98percent), 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.
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