DARSTELLUNG UND CHARAKTERISIERUNG VON 2-CHLORETHYLSUBSTITUIERTEN BENZODIAZAPHOSPHORINANONEN

Abstract

Abstract The reaction of N-methylisatoic anhydride 1 with isopropylamine furnished the N-isopropyl-N'-methyl-substituted anthranilic acid amide 2. Its reaction with phosphorus trichloride led to the P-chlorobenzodiazaphosphorinanone 3. 3 and two further P-chlorobenzodiazaphosphorinanones, 5 and 7, were allowed to react with the amine derivatives, bis(2-chloroethyl)amine hydrochloride, 2-chloroethylamine hydrochloride, and dimethylaminotrimethylsilane, forming the corresponding P(III)-amino derivatives, 4, 6 and 8. Reaction of 8 with elemental sulfur yielded the thiobenzodiazaphosphorinanone 9. Careful hydrolysis of the P-chlorobenzodiazaphosphorinanones 3 and 7 gave rise to compounds 10 and 11, involving the P(:O)H grouping. The oxidation of 6, 12 and 13 to the 2-oxo-benzodiazaphosphorinanones 14–16 was effected in two ways: Aqueous hydrogen peroxide as well as the hydrogen peroxide-urea 1:1 adduct as the oxidizing agent furnished the corresponding λ4P(V) derivatives 14–16 in good yield. A discussion of t...