Frank Borkenhagen, I. Neda, Holger Thönnessen
1996
Citations
0
Influential Citations
3
Citations
Journal
Zeitschrift für Naturforschung B
Abstract
The reaction of N-methylisatoic anhydride with 2-morpholinoethylamine or 1-aminoadamantane furnished N-methyl-N′-(2-morpholinoethyl)anthranilamide 1 and N-methyl-N′- ( l-adamantyl)anthranilamide 2, respectively. 1 and 2 are intermediates in the synthesis of the 2-chloro-3-methyl-1,3,2 λ3-diazaphosphorinones 3 and 4 by reaction of 1 and 2 with PCI3. The reaction of 3 with bis(2-chloroethyl)amine hydrochloride/triethylamine or (2-chloroethyl)amine hydrochloride/triethylamine formed the 2-substituted diazaphosphorinones 5 and 6. Hydrolysis of 3 led to the 2-oxo-λ4P-compound 7. The reaction of 6 with hexafluoroacetone furnished the (λ5) phosphorane 8. 5 reacted with C7H8Cr(CO)4 to form complex 9 whereas oxidation of 5 with the H2O2: urea 1:1 adduct yielded the phosphoryl compound 10. The crystal structure of 1 displays two independent molecules that show different chain conformations. Both molecules form chains parallel to the y-axis by intermolecular N (amide)-H···O(amide) bonds. The crystal structure of 6 shows a half-boat conformation for the phosphorinone ring; the P atom lies out of the plane. Again the molecules are linked by H-bonds into chains parallel to the y-axis.