A novel route to the 5,6-dihydro-4-H-thieno[3,2-b]pyrrol-5-one ring system involving an intermediate substituted-thiophene synthesis

Abstract

A novel route to electron-deficient thienopyrrolones is disclosed. The target heterocycles are concisely constructed by condensation of activated α-or β-halo-substituted acrylonitriles, or ortho-substituted halo, cyano heterocycles with mercaptopyruvate, followed by reduction and subsequent lactamization.

Synthesis of Fluorinated Thiophenes and Their Analogues

“…Ethyl mercaptopyruvate was also transformed into 2-trifluoromethylthiophene in 54% yield by reaction with 2,3dibromo-4,4,4-trifluorobutanenitrile in the presence of triethylamine at 50°C (Scheme 39). 68 The condensation of a trifluoromethylethylene derivative with ethyl thioglycolate in ethanol proceeded analogously (Scheme 39). 69 Additionally, sulfur and perfluoroalkyl functionalities can both be present in the same starting molecule.…”