Stereoselective Synthesis of dialkyl 2-benzoyloxy-3-(N-alkyl-N‘-arylcarbamimidoyl)succinates: A Four Component Reaction

Abstract

An improved four-component reaction of isocyanides is described. The reaction between alkyl isocyanides, dialkyl acetylenedicarboxylates, aromatic amines and benzoic acid in dichloromethane at room temperature leads to dialkyl 2-benzoyloxy-3-(N-alkyl-N′-arylcarbamimidoyl)succinates in good yields

Four-component Reaction between Aryl Aldehydes, Ethyl Cyanoacetate and Dimethyl Acetylenedicarboxylate in the Presence of Cyclohexyl Isocyanide

“…20 Reaction of the isocyanide-DMAD adduct with aromatic-substituted acetic acids has been reported to afford 2,5-diaminofuran derivatives in the presence of two equivalents of an isocyanide. 21 In the context of our previous works on IMCRs, [14][15][16]22 we now report the results of our investigations on the reaction of cyclohexyl isocyanide 1 with dimethyl acetylenedicarboxylate 2, aryl aldehydes 3, and ethyl cyanoacetate 4 to afford aminocyclopentadienes 5.…”

Four-Component Reaction of Isocyanides, Acetylenic Esters, and Carboxylic Acids for the Synthesis of Functionalised 2,5-diaminofurans

“…21 Reaction of isocyanide-DMAD adduct with aromatic-substituted acetic acids has been reported to afford 2,5-diaminofuran derivatives in the presence of two equivalents of an isocyanide. 22 In the context of our previous work on IMCRs, [15][16][17]23 we now report the results of our investigations on the reaction of isocyanides and dialkyl acetylenedicarboxylates (DAADs) in the presence of aliphatic carboxylic acids such as acetic acid, propionic acid, trifluoroacetic acid, formic acid and succinic acid.…”

A simple and convenient approach to the synthesis of aminofuropyrimidindiones

“…In 2007, some unexpected results were obtained when barbituric acid was used. 20 The condensation reactions between alkyl isocyanide, substituted benzaldehydes and barbituric acid were performed in water/acetonitrile (1:1) under reflux conditions to give N-alkyl-N-[aryl- (2,4,6trioxohexahydropyrimidin-5-yl)methyl]formamides in 3 h.…”