Опубликована статья: Synthesis of pyrrole-ferrocene ensembles and their rearrangement into 2-(ferrocenylmethyl)-1,2-dihydro-3H-pyrrol-3-ones  // Ol'ga A.Tarasova, Nina A.Nedolya, Alexander I.Albanov, IrinaYu.Bagryanskaya,  Boris A.Trofimov (DOI: 10.1016/j.jorganchem.2020.121651)

Abstract

The lithiation of (ferrocenylmethoxy)allene followed by sequential reaction with isothiocyanate and S-alkylation of the adduct gives the corresponding alkyl buta-2,3-dienimidothioate (1-aza-1,3,4-triene), which in the presence of CuI or CuBr cyclizes into (ferrocenylmethoxy)/sulfanyl-substituted pyrrole ring. The process is carried out in one or two preparative steps depending on an alkylating agent. A novel unexpected rearrangement of the synthesized 3-(ferrocenylmethoxy)-2-sulfanyl-1H-pyrroles into 2-(ferrocenylmethyl)-2-sulfanyl-1,2-dihydro-3H-pyrrol-3-ones, proceeding in CDCl3 at room temperature or in toluene under heating, is discovered. The transformation of the 3-(ferrocenylmethoxy)-1H-pyrroles into 1,2-dihydro-3H-pyrrol-3-ones is most likely the result of the formal [1,3]-O-to-C-rearrangements (acid-induced or thermal, respectively).

https://www.sciencedirect.com/science/article/pii/S0022328X20305544

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