A Novel Synthesis of N-Unsubstituted β-Enamino Thioesters from 3-Arylisoxazoles and 3-Aryl-5-phenylthio-2-isoxazolines

Abstract

A novel procedure for the synthesis of N-unsubstituted β-enamino thioesters, (Z)-S-phenyl 3-amino-3-arylprop-2-enethioates, from 3-arylisoxazoles or 3-aryl-5-phenylthio-2-isoxazolines is described and a plausible mechanism for the reaction is proposed. Some examples of conversion of one β-enamino thioester [(Z)-S-phenyl 3-amino-3-phenylprop-2-enethioate] into N-unsubstituted β-enaminoacyl derivatives (β-enamino esters, β-enamino amides, and β-keto amides) are also reported.

Key words

cycloaddition - lithiation - nucleophilic addition - 3-arylisoxazoles - β-enaminoacyl derivatives

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For preliminary results: Vitale P., Di Nunno L., Scilimati A.; ORG-PO-55. XXIII Congresso Nazionale della Società Chimica Italiana, 2009: http://www.soc.chim.it/files/divisioni/chimorg/programma%20DivChimOrg%20SCI2009_def020709.pdf