1042222-83-2Relevant academic research and scientific papers
A practical and efficient green synthesis of β-aminophosphoryl compounds via the aza-michael reaction in water
Matveeva, Ekaterina V.,Shipov, Anatoly E.,Odinets, Irina L.
scheme or table, p. 698 - 706 (2011/06/23)
Application of water as a solvent (without any cosolvent) promotes the aza-Michael reaction of diethyl vinylphosphonate and diphenylvinylphosphine oxide with a wide range of N-nucleophiles. The solubility of the starting phosphorus substrate in water does not play a crucial role in the reaction course, decreasing to some extent the reaction rate. The reaction can be performed either at room temperature or under reflux to afford the corresponding β-aminophosphonates and β-aminophosphine oxides in excellent yields and of high purity via a simple freeze-drying isolation procedure. Application of basic catalysts makes possible the addition of weak nucleophiles such as a-amino acids and their phosphorus analogues; that is, a-aminophosphonic acids. The aqueous aza-Michael reaction allowed us to easily perform double phosphorylation of primary amines including polyamines using a reactant ratio (phosphorus substrate: amine) of 2:1. Copyright Taylor & Francis Group, LLC.
Efficient synthesis of racemic β-aminophosphonates via aza-Michael reaction in water
Matveeva, Ekaterina V.,Petrovskii, Pavel V.,Odinets, Irina L.
scheme or table, p. 6129 - 6133 (2009/04/05)
Water as a solvent significantly accelerates the addition of various amines to diethyl vinylphosphonate to yield β-aminophosphonates without any catalyst compared to known procedures for such aza-Michael reactions. The products are obtained in quantitative yields and high purity over short reaction times. Using a reactant ratio (vinylphosphonate/amine) of 2:1 resulted in double phosphorylation of primary amines.
