A method of synthesis of phosphinic acids on the basis of hypophosphites: VII. Synthesis of pseudo-γ-aminobutanoyl peptides and other phosphinic analogs of γ-aminobutyric acid
                                
                                    
                                        作者:V. V. Ragulin                                    
                                    
                                        DOI:10.1134/s107036320809003x
                                    
                                    
                                        日期:2008.9
                                    
                                    A method of synthesis of pseudo-gamma-aminobutanoyl peptides and other phosphinic analogs of gamma-aminobutyric acid from hypophosphites is suggested. Silyl phosphonites formed by in situ addition of bis-(trimethylsilyl) hypophosphite to the corresponding alpha-substituted acrylates, styrene, or vinyl phosphonate used as unsaturated components in the synthesis react in situ with N-(omega-bromoalkyl)phthalimides by an Arbuzov reaction scheme, affording omega-(phthalimido)alkylphosphinic acids possessing beta-substituted beta-(alkoxycarbonyl)ethyl, beta-phenylethyl, or beta-(diethoxyphosphinoyl)ethyl substituents. Acid hydrolysis of these reaction products gives the target aminophosphinic acids: phosphinic analogs of gamma-aminobutyric acid.