Synthesis of New Organophosphorus Compounds based on Three-Component Reaction between Trimethyl phosphite and Acetylenic Ester in the Presence of Modafinil

Organophosphorus compounds are important substrates in the study of biochemical processes.1,2 For a long time, phosphorus analogues of amino acids, in which the carboxylic acid group is replaced with phosphonate group, P(O)(OR)2, have attracted particular interest in preparing analogues of numerous natural products.3,4 In this area, β-amido phosphonates as isosteres of β-amino acids occupy an important place and reveal diverse and interesting biological and biochemical properties.5,6 There are several methods for synthesis of β- amidophosphonates. In most of them, nucleophilic trivalent phosphorus is attached to an electrophilic carbon.7,8 Considering these strategies and importance of multicomponent reactions in organic synthesis, as a part of our study on the development of new routes to organophosphorus compounds,9,10 we now report on the reaction of (MeO)3P and diethyl acetylenedicarboxylate (DEAD) in the presence of modafinil to produce β-amidophosphonates, phosphonates, and stable phosphorimidates.11,12