[Chemical and pharmacological research on pyran derivatives. XII. Bis-(beta-chloroethyl)amino-substituted chromones and benzochromones].

By the reaction of phenols or naphthols with N,N-bis-(beta-methoxyethyl)ethoxycarbonylacetamide in the presence of phosphorus oxychloride the preparation of bis-(beta-methoxyethyl)amino substituted chromones or benzochromones was achieved. Treatment of these compounds with hydriodic acid at 95 degrees and then with thionyl chloride gave rise to the formation of the corresponding bis-(beta-chloroethyl)amino derivatives. When beta-naphthols reacted with N-ethoxycarbonylacetylmorpholine 1-oxo-3-morpholino-1H-naphtho[2,1-b]pyrans were obtained. These compounds as well as the corresponding 3-bis-(beta-methoxyethyl)amino derivatives afforded 1-oxo-3-bis-(beta-iodoethyl)amino-1H-naphtho[2,1-b]pyrans by treatment with hydriodic acid at reflux. The latter compounds were also easily transformed into 3-bis-(beta-chloroethyl)amino derivatives by reaction with phosphorus oxychloride in N,N-dimethylformamide. Pharmacological screening of some of the compounds described indicated no tumor-inhibiting activity.