Abstract
Reaction of ethyl (Z)-3-(heteroaryl/aryl)-2-((triphenyl-λ5-phosphaneylidene) amino) acrylates intermediates with 2,3-thiophenedicarboxaldehyde was used in novel Tandem three consecutive reactions: aza-Wittig, imine condensation and electrophilic heteroaromatic cyclization to obtain a series of indolizines. A tentative mechanism of this reaction is proposed.
Highlights
IntroductionThe indolizine containing molecules became a challenging synthetic target and several strategic routes to build completely new structures in this family or to obtain known molecules in reduced number of steps or avoiding expensive reagents were proposed [36] [37] [38]
Reaction of ethyl (Z)-3-(heteroaryl/aryl)-2-((triphenyl-λ5-phosphaneylidene) amino) acrylates intermediates with 2,3-thiophenedicarboxaldehyde was used in novel Tandem three consecutive reactions: aza-Wittig, imine condensation and electrophilic heteroaromatic cyclization to obtain a series of indolizines
In this work we report a new Tandem process of three consecutive reactions: aza-Wittig, Imine condensation and Electrophilic Aromatic Substitution, for obtaining heterocyclic structures of indolizines
Summary
The indolizine containing molecules became a challenging synthetic target and several strategic routes to build completely new structures in this family or to obtain known molecules in reduced number of steps or avoiding expensive reagents were proposed [36] [37] [38]. In this context, we developed in this study a new strategy toward the title compounds using the iminophosphorane intermediates and their reaction with 2,3-thiophenedicarboxaldehyde. This coupling is leading to the formation of the molecules derived from alkaloids core, that of indolizines
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