One-pot synthesis, antimicrobial activities, and drug-likeness analysis of some novel 1,2-benzoxaphosphinines, phospholobenzofuran, and chromonyl/coumarinyl/indenonyl phosphonate

Abstract

Some novel phosphorus compounds of types 1,2-benzoxaphosphinines, phospholo-[3,4-b][1]benzofuran, and chromonyl/coumarinyl/indenonyl phosphonates were achieved. The methodology depended on reaction of 1-(2-hydroxyphenyl)-3-phenylpropane-1,3-dione (1) with diethyl phosphite in the absence and presence of electrophilic reagent. Reaction of substrate 1 with diethyl phosphite in the presence of a base afforded 3-benzoyl-4-hydroxy-2-oxido-2H-1,2-benzoxaphosphinine (2), white its reaction with diethyl phosphite in the presence of ammonia, formaldehyde and chloroacetyl chloride under basic conditions gave the corresponding 4-ethoxy-4-oxido-2-phenyl-3,4-dihydro[1,2]benzoxaphosphinino[3,4-b] pyrrole (6) and 1-benzoyl-2-ethoxy-3-hydroxy-2-oxido-2H-phospholo[3,4-b][1]benzofuran (7), respectively. In addition, treatment of compound 1 with diethyl phosphite in the presence of DMFDMA, ethyl chloroacetate and oxalyl chloride under the same conditions led to the formation of chromonyl/coumarinyl/indenonyl phosphonates 3, 8, and 10, respectively, in moderate yields. The reaction mechanisms for the formation of these products were presented and explained. The molecular structures of products were deduced by spectral and analytical tools. The antimicrobial activity for the novel products were evaluated. The antimicrobial results were supported by SwissADME server based in silico computations. Both products 6 and 10 showed excellent antimicrobial properties.

Graphical Abstract

Keywords:

• Antimicrobial
• 1,2-benzoxaphosphinine
• chromone
• coumarin
• diethyl phosphite
• diketone
• one-pot
• phosphonate

Additional information

Funding

The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding this work through large research groups program under grant number (RGP.2/8/43).