Synthesis and reactivity of michael adducts of lithiated 2,5-dimethoxy-N-pivaloylanilines and arylidenemalonates

Article abstract of DOI:10.1016/S0040-4020(97)00034-3

Michael addition of lithiated 2,5-dimethoxypivaloylaniline to diisopropyl arylidenmalonates, followed by acid cyclization, affords 5,8-dimethoxy-4-aryl-3,4-dihydro-2(1H)quinolinones (5). These compounds are very inert to the 3,4-dehydrogenation, but were easily transformed to 4-aryl-3,4-dihydro-(1H)quinoline-2,5,8-triones (10) which, through Diels-Alder heterocyclization, gave 4-aryl-3,4-dihydro-1,8-diazaanthracene-2,9,10-triones (16).