Stereoselective One-Pot Synthesis of Functionalised Phosphonates by Three-Component Reaction between Trimethylphosphite, Dialkyl Acetylenedicarboxylates and Aldehyde Semicarbazones

Abstract

Three-component reaction between dialkyl acetylenedicarboxylates, trimethylphosphite, and aldehyde semicarbazones leads to functionalised phosphonates in good yields.

Stereoselective synthesis of 3-[2-(dialkoxyphosphoryl)-1,2-dialkoxycarbonyl-ethyl]-4-hydroxycoumarins by reaction between trialkyl phosphites, dialkyl acetylenedicarboxylates and 4-hydroxycoumarin

“…15 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 ylide intermediate. [16][17][18][19][20][21][22] In continuation of our works on the reaction between trivalent phosphorus nucleophiles and acetylenic esters in the presence of organic NH, OH, or CH-acids, [17][18][19][20][21][22][23] here we report the results of our study on the reaction between dialkyl acetylenedicarboxylates (DAADs) and trialkyl phosphites in the presence of 4-hydroxycoumarin.…”

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.…”

Synthesis of Functionalised Phosphonates or Phosphoranes by Reaction between Trialkyl Phosphites or Triphenylphosphine, Dimethyl Acetylenedicarboxylate and Aldehyde Ethyl Carbazones

“…[1][2][3] Reaction between phosphites and acetylene diesters in the presence of an acidic organic compound is known to produce phosphite ylides as the intermediate or the final product. [4][5][6][7][8] We recently reported the reaction between trimethyl phosphite, dimethyl acetylenedicarboxylate (DMAD) and aldehyde semicarbazones forming phosphonate derivatives 1 (Fig. 1).…”

“…1). 5 When tributyl phosphite was used, phosphite ylides 2 were isolated as stable crystalline solids. 6 Three-component reaction of aldehyde semicarbazones, DMAD and triphenylphosphine has been reported to produce phosphoranes 3.…”

“…In continuation of our work on the reaction between trivalent phosphorus nucleophiles and acetylene diesters in the presence of organic NH, OH, or CH-acids, [5][6][7][8][9][10][11][12] we here report the results of our study on the reaction between DMAD and trialkyl phosphites or triphenylphosphine in the presence of ethyl carbazones of aromatic aldehydes. Thus, the reaction of DMAD ( 6) with trialkyl phosphite 7 in the presence of ethyl carbazone 5 leads to the corresponding phosphonate 8 in fairly high yields (Scheme 1).…”