Chinnam S., Potturi C., Maddila S., Muttana V.B.R., Ediga A., Chinnam V.
Department of Chemistry, Sri Venkateswara Univeristy, Tirupati, India; Department of Environmental Sciences, Sri Rama Engineering College, Tirupati, India; School of Chemistry, University of KwaZulu-Natal, West Ville Campus, Chilten Hills, Durban -4000, South Africa; Department of Biochemistry, Sri Venkateswara University, Tirupati, India; Department of Chemistry, KVR College, Nandigama, India
Chinnam, S., Department of Chemistry, Sri Venkateswara Univeristy, Tirupati, India; Potturi, C., Department of Environmental Sciences, Sri Rama Engineering College, Tirupati, India; Maddila, S., School of Chemistry, University of KwaZulu-Natal, West Ville Campus, Chilten Hills, Durban -4000, South Africa; Muttana, V.B.R., Department of Chemistry, Sri Venkateswara Univeristy, Tirupati, India; Ediga, A., Department of Biochemistry, Sri Venkateswara University, Tirupati, India; Chinnam, V., Department of Chemistry, KVR College, Nandigama, India
A facile method has been developed for the synthesis of novel α-aminophosphonates 5a-j by the one-pot three component reaction of equimolar quantities of 4-amino-N-2-thiazolyl-benzenesulfonamide (Sulfathiazole) (1), dimethyl phosphite (2) and various aldehydes (4a-j) in dry toluene at reflux conditions via Kabachinik-Fields reaction in high yields (70-80%) without use of any catalyst. Their chemical structures were established by IR, 1H, 13C, 31P-NMR, mass spectral studies and elemental analyses. All the title compounds exhibited promising antibacterial and antifungal activities.
aldehyde; antifungal agent; bovastin; dimethyl (2 chlorophenyl) [4 (n thiazol 2 ylsulfamoyl)phenylamino]methylphosphonate; dimethyl (2 nitrophenyl) [4 (n thiazol 2 ylsulfamoyl)phenylamino]methylphosphonate; dimethyl (3 chlorophenyl) [4 (n thiazol 2 ylsulfamoyl)phenylamino]methylphosphonate; dimethyl (3 cyanophenyl) [4 (n thiazol 2 ylsulfamoyl)phenylamino]methylphosphonate; dimethyl (3 methoxyphenyl) [4 (n thiazol 2 ylsulfamoyl)phenylamino]methylphosphonate; dimethyl (3 nitrophenyl) [4 (n thiazol 2 ylsulfamoyl)phenylamino]methylphosphonate; dimethyl (3 trifluoromethylphenyl) [4 (n thiazol 2 ylsulfamoyl)phenylamino]methylphosphonate; dimethyl (4 chlorophenyl) [4 (n thiazol 2 ylsulfamoyl)phenylamino]methylphosphonate; dimethyl (4 fluorophenyl) [4 (n thiazol 2 ylsulfamoyl)phenylamino]methylphosphonate; dimethyl (4 nitrophenyl) [4 (n thiazol 2 ylsulfamoyl)phenylamino]methylphosphonate; dimethyl [(3 trifluoromethyl)phenyl] [4 (n thiazol 2 ylsulfamoyl)phenylamino]methylphosphonate; phosphoramidic acid derivative; streptomycin; sulfathiazole; toluene; unclassified drug; antifungal activity; article; Aspergillus flavus; Aspergillus niger; Bacillus subtilis; bacterial strain; carbon nuclear magnetic resonance; catalyst; chemical reaction; controlled study; drug structure; drug synthesis; Escherichia coli; Fusarium oxysporum; infrared spectroscopy; Kabachinik Fields reaction; nonhuman; phosphorus nuclear magnetic resonance; proton nuclear magnetic resonance; Streptococcus bovis