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Synthesis of Thiophene Derivatives on Soluble Polymer-Support Using Gewald Reaction
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2004
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Organic Material ChemistryChemical EngineeringCyanoacetic AcidEngineeringNovel OrganocatalystsPolymer ScienceOrganic ChemistryMicrowave IrradiationChemistryMolecular EngineeringThiophene DerivativesOrganometallic PolymerMicrowave SynthesisSynthetic ChemistryPolymer ChemistryPolymer Synthesis
A variety of thiophene derivatives have been synthesized using poly(ethylene glycol) (PEG) as soluble polymer support. PEG reacted with cyanoacetic acid, DCC and DMAP in CHCl3 under microwave irradiation to give PEG-bound cyanoacetic ester 1. A mixture of 1, elemental sulfur, DIPEA and 2 carried out Gewald reaction under microwave irradiation to afford 3, which was acylated and treated with 1% KCN in methanol to give thiophene derivatives 6. This synthetic method is simple and mild, and the yields are moderate to high.