Three-Component Reaction of Alkyl Isocyanides, Dialkyl Acetylenedicarboxylates and Furan-2-Carboxylic Acid Arylidene-Hydrazides

Abstract

The adduct produced in the reaction between alkyl isocyanides and dialkyl acetylenedicarboxylates was trapped by furan-2-carboxylic acid arylidene-hydrazides to afford highly functionalised ketenimines in good yields. The reaction is characterised by mild conditions, high selectivity, and tolerance to various functional groups.

Three-Component Reaction between Alkyl Isocyanides, Dialkyl Acetylenedicarboxylates, and Carboxylic Acids

“…14 Reaction of the isocyanide-DMAD adduct with aromaticsubstituted acetic acids has been reported to afford 2,5-diaminofuran derivatives in the presence of two equivalents of an isocyanide. 15 In the context of our previous works on isocyanide based multi-component reactions, [9][10][11]16,17 we now report the results of our investigations on the reaction of carboxylic acids and dialkyl acetylenedicarboxylates in the presence of alkyl isocyanides.…”

Synthesis of Ketenimines Derivatives from Reaction between Alkyl Isocyanides and Dialkyl Acetylenedicarboxylates in the Presence of Carboxylic Acid Arylidene-Hydrazides

“…The trapping of the 1:1 intermediate formed between dialkyl acetylenedicarboxylates and isocyanides with OH, NH and CH acids has been widely studied [10][11][12][13][14][15][16] . In continuation of our works on the reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of organic acids [17][18][19] , here we wish to report the results of our studies on the reaction between alkyl isocyanides and dialkyl acetylenedicarboxylates, in the presence of carboxylic acid arylidene-hydrazides.…”

Synthesis of Functionalised 2,5-Diaminofurans by Reaction of Isocyanides, Acetylenic Esters and Acid Anhydrides

“…16 The reaction between two equivalents of an isocyanides, aliphatic carboxylic acids and dialkyl acetylenedicarboxylates has been reported to afford 2,5-diaminofuran derivatives. 17 In the context of our previous work on IMCRs, [9][10][11][17][18][19][20][21] we nowreport the results of our investigations on the reaction of isocyanides and dialkyl acetylenedicarboxylates (DAADs) in the presence of acid anhydrides.…”