Abstract
It is shown that the reaction of aromatic o-diamines having a nitro group in the para position relative to one of the amino groups with acetoacetic esters under mild conditions gives arylaminocrotonates, which are isomerized to ketimines under the influence of acid, are cyclized to dihydro-1,5-benzodiazepinones on heating, and are converted to 1-isopropenylbenzimidazolones under more severe conditions. If the condensation of the nitrodiamine with the acetoacetic acid esters is carried out under severe conditions, the isomeric dihydro-1,5-benzodiazepinone is obtained. Splitting out of an alkylacetate ester to give the corresponding 2-methylbenzimidazole occurs in the condensation of various o-diamines with 2-alkylacetoacetic esters.
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