Synthesis, X-ray structure and antibacterial evaluation of P-[{[bis (dimethylamino)phosphoryl]amino]} (2-chloroquinolin-3-yl) methyl]-, P- (quinolin-3-yl) tetramethylphosphonic diamides

Abstract

A new P-bis [(dimethylamino) phosphoryl] amino} (2-chloroquinolin-3-yl) methyl]- N, N,N',N'- tetramethylphos-phonic diamide  was synthesized by the reaction of  trisdiaminophosphine  to 2-chloroquinolin-3-aldoxime.  The structure of P-bis [(dimethylamino) phosphoryl] amino} (2-chloroquinolin-3-yl) methyl]-     N, N,N',N'- tetramethyl-phosphonic diamide  is confirmed by X-ray diffraction studies.  On the other hand, the neucluphilic attack of aminophosphine on 2-chloroquinolin-3-carboimines produced different products, depending on the stability of dipolar phosphorylhexamethyl amide intermediates. Furthermore, the reaction of 3-((5-oxo-2-phenyl-oxazol-4(5H)-ylidene) methyl) quinolin-2(1H)-one with phosphine yielded alkene adduct, the Z structure is confirmed by X-ray analysis. P-[(2-Chloro-quinolin-3-yl)(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl) methyl]-N,N,N,N,tetramethyl-phosphonic diamide   was obtained  from  reaction  of 4-( (2-chloro-quinolin-3-yl) methylene)-3-methyl-1- phenyl-1H-pyrazol-5(4H)- one  with reagent trisdiaminophosphine.    Antibacterial evaluation of most compounds exhibited moderate activity to Gram positive and Gram-negative bacteria species.