Stereoselective One-Pot Synthesis of Functionalised Phosphonates by three-component reaction between Trialkyl(aryl) Phosphites, Dimethyl Acetylenedicarboxylate and indan-1,3-dione or N,N′-dimethylbarbituric acid

Abstract

Protonation of the reactive intermediate produced in the reaction between trialkyl(aryl) phosphites and dimethyl acetylenedicarboxylate by CH- acids such as indane-1,3-dione and N,N′-dimethylbarbituric acid leads to functionalised phosphonates in good yields.

Synthesis of Benzoindolizine Derivatives by Reaction of Trimethyl Phosphite, Dialkyl Acetylenedicarboxylates and Isoquinolinium or Quinolinium Bromides

“…7 There are other recent reports on the reaction between phosphites and acetylenic esters in the presence of an acidic organic compound, all proceeding through a phosphite ylide intermediate. [8][9][10][11][12][13][14] In continuation of our previous work on the reaction between trivalent phosphorus nucleophiles and acetylenic esters in the presence of organic NH, OH, or CH-acids, [9][10][11][12][13][14] we report here the results of our study on the reaction between dialkyl acetylenedicarboxylates and trialkyl phosphites such as triethyl phosphite, tributyl phosphite or trimethyl phosphite in the presence of C-H acidic compounds isoquinolinium or quinolinium bromides.…”

Diastereoselective Synthesis of Functionalised Phosphonates by Three-Component reaction between Phosphites, Acetylene Diesters and Formanilides

“…The presence of phosphorus atom in the product is helpful for determining its relative configuration using the carbon-phosphorus coupling constants. In continuation of our previous work on the reaction between trialkyl phosphites and acetylene diesters in the presence of organic acidic compounds, [13][14][15][16] here we report the reaction between dialkyl acetylenedicarboxylates (DAADs), triethyl phosphite or triphenyl phosphite and formanilide derivatives to produce functionalised succinate phosphonates in good yields (Scheme 1).…”

“…For example, the reaction between trialkyl phosphites and dialkyl acetylenedicarboxylates (DAAD) in the presence of organic N-H, OH and C-H acidic compounds has been reported to produce phosphite ylides which may be isolated as stable compounds 9,10 or hydrolysed to phosphonate derivatives. [10][11][12][13][14][15][16] These phosphonates are usually formed in a stereoselective manner. The presence of phosphorus atom in the product is helpful for determining its relative configuration using the carbon-phosphorus coupling constants.…”

An efficient one-pot synthesis of dialkyl 8a-acetylamino-8-oxo-8,8a-dihydro-2H-1-oxacyclopenta[α]indene-2,3-dicarboxylate derivatives

“…The threecomponent reaction between triphenylphosphine, acetylenic esters and an organic acidic compound has been reported to produce phosphorus ylides which may further undergo intramolecular Wittig reactions to produce unsaturated hetro-or carbo-cyclic compounds in a one-pot process. [4][5][6] In continuation of our previous work on the reaction between trivalent phosphorus nucleophiles and acetylene diesters in the presence of acidic organic compounds [7][8][9][10][11][12][13][14] we wish to report herein the results of our studies on the reaction between dialkyl acetylenedicarboxylates and triphenylphosphine in the presence of N-(2-hydroxy-1,3-dioxoindan-2-yl)amide derivatives 3.…”