An Efficient One-Pot Synthesis of 5-Sulfanyl-1-[2-(vinyloxy)ethyl]-1H-pyrrol-2-amines as Precursors of 1-Vinylpyrroles

Abstract

Sequential processing of monolithiated tertiary propargylamines with 2-(vinyloxy)ethyl isothiocyanate and t-BuOK–DMSO results in the introduction of a highly reactive 2-(vinyloxy)ethyl group at the position 1 of the pyrrole ring thus formed. In this way, a series of new 5-sulfanyl-1-[2-(vinyloxy)ethyl]-1H-pyrrol-2-amines were obtained in a yield of up to 92%. The latter in the presence of t-BuOK–DMSO system (110–120 °C, 10–15 min) eliminates vinyl alcohol to give rare-functionalized 1-vinylpyrroles, namely 5-sulfanyl-1-vinyl-1H-pyrrol-2-amines, inaccessible by the known methods.

Key words

5-sulfanyl-1-[2-(vinyloxy)ethyl]-1H-pyrrol-2-amines - 5-sulfanyl-1-vinyl-1H-pyrrol-2-amines - propargylamines - 2-(vinyloxy)ethyl isothiocyanate - alkylating agents - deprotonation - isomerization - C–O bond cleavage

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