Synthesis of unsaturated amidine derivatives by three component reaction of alkyl isocyanides, dialkyl acetylenedicarboxylates and pyrrole or indole

Abstract

The reactive intermediate generated by the reaction of alkyl isocyanides and dialkyl acetylenedicarboxylates was trapped by pyrrole or indole to produce unsaturated amidine derivatives in good yields.

One-pot synthesis of highly functionalized stable ketenimines of 2,2,2-trifluoro-N-aryl-acetamides

“…The trapping of the 1:1 intermediate formed between dialkyl acetylenedicarboxylates and isocyanides with OH, NH, and CH acids has been widely studied [20][21][22][23][24]. In continuation of our works on the reaction between isocyanides and acetylenic esters in the presence of organic acids [25][26][27][28], in this paper we present the results of an extended investigation on the reactivity of the intermediate zwitterion with 2,2,2-trifluoro-N-aryl-acetamides as N-H acids in dichloromethane leading to the formation of thermally stable ketenimine derivatives in good yields. Alkyl isocyanides 1 and dialkyl acetylenedicarboxylates 2 in the presence of 2,2,2-trifluoro-N-aryl-acetamides 3 undergo a smooth 1:1:1 addition reaction in dichloromethane at ambient temperature to produce dialkyl 2-(N-(aryl)-2,2,2-trifluoroacetamido)-3-(alkylimino) methylene-succinate derivatives 4 in excellent yields (Scheme 1).…”

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

“…There has been intense interest in their addition reactions, such as cycloaddition [3][4][5] Multicomponent reactions (MCRs), by virtue of their convergence, productivity, facile execution and generally high yields of products, have attracted much attention in the area of combinatorial chemistry [6][7][8] , of pivotal importance are the isocyanidebased MCRs 9 . 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.…”

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.…”