Competition of the R3P/DAAD and RNC/DAAD Zwitterions in Their Production and Reaction with Aromatic Carboxylic Acids: A Novel Binucleophilic System for Three-Component Synthesis of 2-Aminofurans

Abdolali Alizadeh; Sadegh Rostamnia; Long-Guan Zhu

doi:10.1055/s-2008-1067028

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Competition of the R₃P/DAAD and RNC/DAAD Zwitterions in Their Production and Reaction with Aromatic Carboxylic Acids: A Novel Binucleophilic System for Three-Component Synthesis of 2-Aminofurans

Abdolali Alizadeh*^a, Sadegh Rostamnia^a, Long-Guan Zhu^b
^a Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran 18716, Iran
Fax: +98(21)88006544; e-Mail: aalizadeh@modares.ac.ir;
^b Chemistry Department, Zhejiang University, Hangzhou 310027, P. R. of China

Abstract

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Abstract

We recently reported a new class of triphenylphosphine and isocyanide based multicomponent reactions (Ph₃P/DAAD and IMCRs/DAAD) mediated by R₃P/DAAD and RNC/DAAD zwitterionic intermediates in the presence of CH, OH, and NH acids. Herein, the reactions of Huisgen 1:1 zwitterionic intermediates, generated from dialkyl acetylenedicarboxylates (DAAD), trivalent phosphorus reagents, and isocyanides, with aromatic carboxylic acids as initial proton source are investigated. This novel binucleophilic (R₃P-RNC/DAAD) system afforded 2-aminofuran derivatives.

Key words

isocyanide - trialkyl phosphine - trialkyl phosphite - dialkyl acetylenedicarboxylate - aromatic carboxylic acid - multicomponent reaction - aminofuran

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