Synthesis of 5-aryl-1,3-dimethyl-6-(alkyl- or aryl-amino) furo [2,3-d]pyrimidine derivatives by reaction between isocyanides and pyridinecarbaldehydes in the presence of 1,3-dimethylbarbituric acid

Abstract

5-Aryl-6-(alkyl- or aryl-amino)-1,3-dimethylfuro [2,3-d]pyrimidine derivatives were obtained by in situ reaction alkyl or aryl isocyanides and pyridinecarbaldehyde derivatives in the presence of 1,3-dimethylbarbituric acid in dichloromethane without any prior activation or modifications.

Recent applications of barbituric acid in multicomponent reactions

“…16 The synthesis, tautomerism, acid-base properties of barbituric acids and their use for the construction of organometallic and coordination compounds, as well as coordination polymers and supramolecular assemblies has been also reviewed. 21 The first step may involve a Knoevenagel condensation between the aldehyde 4 and 1,3-dimethylbarbituric acid 1 for the formation of the stable intermediate enone A, which undergoes nucleophilic attack by isocyanide to generate adduct B. Such A series of new furo [2,3-d]pyrimidine derivatives 6 were obtained by three-component condensation reaction of isocyanides 5, aldehydes 4 and 1,3-dimethylbarbituric acid 1 at room temperature without any prior activation or modifications (Scheme 2).…”

Three-Component Reaction between alkyl(aryl) Isocyanides and Dialkyl Acetylenedicarboxylates in the Presence of Ethyl Trifluoroacetate

“…20,21 There are a number of reports of iminolactones synthesis. [22][23][24] In continuation of our previous works on IMCRs, [25][26][27][28][29][30][31][32][33] we now report the result of our investigation of the reaction between alkyl(aryl) isocyanides 1 and dialkyl acetylenedicarboxylates 2 in the presence of ethyl trifluoroacetate 3 in refluxing CH 2 Cl 2 .…”

Synthesis of 1‐(Cyclohexylamino)‐2‐(aryl)pyrrolo[1,2‐a]quinoline‐3‐carbonitrile Derivatives Using a Mild, Four‐Component Reaction

“…Because of the aforementioned finding and as a part of our ongoing research program on the IMCRs , we report herein the synthesis of substituted 1‐(cyclohexylamino)‐2‐(aryl)pyrrolo[1,2‐a]quinoline‐3‐carbonitrile derivatives 5 by a four‐component condensation reaction (Scheme ).…”