- Efficient one-pot conversion of 6-methyl-2-nitroaniline into 1-alkyloxy-2-alkyl-4-methyl-, 1-benzyloxy-2-phenyl-4-methyl-, and 1-allyloxy-4-methyl-2-vinyl-benzimidazole
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6-Methyl-2-nitroaniline reacts with alkyl, benzyl and allyl halides and NaH as base, to afford 1-alkoxy-2-alkyl-, 1-benzyloxy-2-aryl- and 1-allyloxy-2-vinyl-benzimidazoles in good to excellent yields (73-98%), via a novel one-pot N-alkylation-heterocycliz
- Gardiner,Loyns
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p. 819 - 827
(2007/10/02)
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- Synthesis of 1-Alkoxy-2-Alkyl-Benzimidazoles from 2-Nitroanilines via Tandem N-Alkylation-Cyclization-O-Alkylation
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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.
- Gardiner, John M.,Loyns, Colin R.,Schwalbe, Carl H.,Barrett, Garry C.,Lowe, Philip R.
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p. 4101 - 4110
(2007/10/02)
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