Novel Three-Component Route to Diastereoselective Synthesis of Trisubstituted Vinylphosphonates Using Phosphites, Acetylenic Esters, and Aroyl Chlorides

Abstract

Trisubstituted vinylphosphonates have been prepared via three-component reaction using phosphites, acetylenic esters, and aroyl chlorides in good yields. A variety of phosphites, activated acetylenes, and aroyl chlorides have been successfully employed in these reactions. In addition, three-component synthesis of vinylphosphonate provides exclusive E-olefin stereochemistry.

Metal–organic frameworks as a very suitable reaction inductor for selective solvent-free multicomponent reaction: IRMOF-3 as a heterogeneous nanocatalyst for Kabachnik–Fields three-component reaction

“…Organic-inorganic hybrid porous IRMOF-3 would make the materials hydrothermal stable and hydrophobic and thus provide the materials with improved catalytic properties during applications for organic small molecules [11][12][13][14][15][16][17]. For these reasons and in our continuing interest in the synthesis and application of the organic-inorganic hybrid nanoporous material in catalyst and multicomponent reactions fields [18][19][20][21][22][23][24], we report herein our results for the application and direct using of the unfunctionalized IRMOF-3 as an suitable, efficient and green catalyst for the threecomponent condensation (3-CRs) of an amine, aldehyde and phosphite without any solvent, salts and additives with excellent yields of biological and medicinal [25][26][27] interest a-aminophosphonates (Scheme 1).…”

Four-Component Reaction between Trimethyl Phosphite, Aroyl Chlorides and Dialkyl Acetylenedicarboxylate with Benzoic Acid Hydrazide

“…The structures of compounds 5a-h were deduced from their elemental analyses and their IR, 1 H NMR, 13 C NMR spectra. The mass spectrum of compound 5a showed the molecular ion peak at 409.…”

“…IR spectra were recorded on a Shimadzu IR-470 spectrometer. 1 H and 13 C NMR spectra were recorded on Bruker DRX-500 Avance spectrometer in solution in CDCl 3 using TMS as an internal standard. The chemicals employed in this work were purchased from Fluka (Buchs, Switzerland) and were used without further purification.…”

“…The diastereoselective synthesis of a novel series of dialkyl (E)-2-(dialkoxyphosphoryl)-3-(aroyl)-2-butenedioate derivatives (4) using the reaction of trialkyl phosphite and an acetylenic ester with various aroyl chlorides via one-pot MCRs was reported in 2010. 13 In continuation of our work on the reaction between trivalent phosphorus nucleophiles and acetylenic esters in the presence of organic NH, OH, or CH-acids, [14][15][16][17][18][19][20][21][22][23] we wish to report the results of our study on the reaction between trimethyl phosphite, dialkyl acetylenedicarboxylates and aroyl chlorides in the presence of benzoic acid hydrazide.…”