Formation and reactions of N-alkyl-2,2-dichlorobenzoylacetanilides

N-Alkylbenzoylacetanilides 1a exhibit a marked deactivation toward nuclear chlorination by sulfuryl chloride as compared to the corresponding N-dealkylated substrates. The acid-catalyzed cyclization of certain N-isopropylbenzoylacetanilides to the corresponding 1-isopropylquinolinones is described. Another example of an apparent intramolecular, two-substituent, migration accompanying indenoquinolinone synthesis is reported.