Heterocyclische 1,4-Naphthochinonderivate, 1. Mitt.: Zur Reaktion von 2-Chlor-3-chloracetylamino-1,4-naphthochinon mit Anilin

Heterocyclic 1,4-Naphthoquinone Derivatives, I: Reaction of 2-Chloro-3-chloroacetylamino-1,4-naphthoquinone with Aniline. 2-Chloro-3-chloroacetylamino-1,4-naphthoquinone ( 3 ) reacts with aniline ( 4 ) in molar ratio 1:2 to give 2-anilino-3-chloroacetylamino-1,4-naphthoquinone ( 6 ). This is an intermediate at the molar rate 1:1 and undergoes acid catalyzed cyclization to give 2-chloromethyl-4,9-dihydro-1-phenyl-1H-naphtho[2,3-d]imidazole-4,9-dione ( 10 ). Base catalyzed reaction of morpholine ( 8 ) and 6 gives also 10 , which alkylates 8 to give 4,9-dihydro-2-(4-morpholinomethyl)-1-phenyl-1H-naphtho-[2,3-d]imidazole-4,9-dione ( 7 ).