Stereoselective One‐Pot Synthesis of Functionalized Phosphonates by Three‐Component Reaction Between Trimethylphosphite, Dialkyl Acetylenedicarboxylates and Aldehyde Semicarbazones.

Abstract

Organo-phosphorus compounds S 0080 Stereoselective One-Pot Synthesis of Functionalized Phosphonates by Three-Component Reaction Between Trimethylphosphite, Dialkyl Acetylenedicarboxylates and Aldehyde Semicarbazones. -Advantages of the present method are the neutral conditions and simple mixing of the substances without any activation. -(ANARY-ABBASINEJAD*, M.; ASCARRIAN, N.; J. Chem. Res. 2007, 1, 11-13; Dep. Chem., Islamic Azad Univ., Yazd, Iran; Eng.) -H. Haber 29-155

Three-component and One-Pot Reaction between Trimethyl Phosphite, Dimethyl Acetylenedicarboxylate and Ethyl 4-Aryl-2,4-Dioxobutanoates

“…Compounds 4a-c have been described previously. 21 The structures of compounds 4d-h were confirmed by IR, 1 H NMR, 13 C NMR, and mass spectroscopic data. For example, the 1 H NMR spectrum of 4d displayed signals for vicinal methine protons at 3.85 and 4.80, which appeared as doublets with 3 J HH value of 1.9 Hz.…”

“…IR spectra were recorded on a Shimadzu IR-470 spectrometer. 1 H and 13 C NMR spectra were recorded on Bruker DRX-300 Avance spectrometer at solution in CDCl 3 using TMS as internal standard. The chemicals used in this work were purchased from Fluka (Buchs, Switzerland) and were used without further purification.…”

“…10 There are some other recent reports on the reaction between phosphites and acetylenic esters in the presence of an acidic organic compound, all of them proceeding through a phosphite ylid intermediate. [11][12][13][14][15][16][17][18][19][20] In 1998, it was reported that the reaction of ethyl 4-aryl-2,4dioxobutanoates and dimethyl acetylenedicarboxylate in the presence of triphenylphosphine affords cyclobutene derivatives 21 . In continuation of this work, we now report the results of our study on the reaction between dimethyl acetylenedicarboxylate (DMAD) and trimethyl phosphite in the presence of ethyl 4-aryl-2,4-dioxobutanoates.…”