Synthesis of pyrrole-ferrocene ensembles and their rearrangement into 2-(ferrocenylmethyl)-1,2-dihydro-3H-pyrrol-3-ones

Sequential processing of monolithiated tertiary propargylamines with 2-(vinyloxy)ethyl isothiocyanate and t-BuOKDMSO results in the intro-duction 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 was 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.

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Reactions of Acetylenic and Allenic Carbanions with Heterocumulenes: A Straightforward Route to Fundamental Heterocycles

Nedolya

2023

Russ J Org Chem

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Synthesis of pyrrole-ferrocene ensembles and their rearrangement into 2-(ferrocenylmethyl)-1,2-dihydro-3H-pyrrol-3-ones

Cited by 4 publications

References 130 publications

Ferrocenes and Other Sandwich Complexes of Iron

Ferrocenes and Other Sandwich Complexes of Iron

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

Reactions of Acetylenic and Allenic Carbanions with Heterocumulenes: A Straightforward Route to Fundamental Heterocycles

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