One pot synthesis of alpha-aminophosphonates containing bromo and 3,4,5-trimethoxybenzyl groups under solvent-free conditions.
New alpha-aminophosphonates were synthesized by the Kabachnik-Fields reaction of 3,4,5-trimethoxybenzaldehyde (TMB) with p- or m-bromoaniline and a dialkyl phosphite under solvent-free conditions. TMB was prepared from gallic acid via a four step synthetic sequence involving etherification, esterification, hydrazidation and potassium ferricyanide oxidation. The structures of all synthesized compounds were confirmed by elemental analysis, IR, 1H-, 13C- and 31P-NMR spectral data. Compound 7g was also characterized by X-ray crystallography. A half-leaf method was used to determine the in vivo curative efficacy of the eight title products against tobacco mosaic virus (TMV). It was found that compounds 7g and 7h possess good in vivo curative effects against TMV.
Li
Caihong
C
Center for Research and Development of Fine Chemicals, Guizhou University, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guiyang, 550025, PR China. licaihong2004@163.com
Song
Baoan
B
Yan
Kai
K
Xu
Gangfang
G
Hu
Deyu
D
Yang
Song
S
Jin
Linhong
L
Xue
Wei
W
Lu
Ping
P
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry; D012997:Solvents; D014026:Nicotiana / Q000187:drug effects*; D014027:Tobacco Mosaic Virus / Q000187:drug effects*
D000998:Antiviral Agents; D063065:Organophosphonates; D012997:Solvents