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

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

Journal

Journal of Organometallic Chemistry
ISSN: 0022-328X

Output data

Year: 2021, Volume: 933, Article number : 121651, Pages count : DOI: 10.1016/j.jorganchem.2020.121651

Tags

(Ferrocenylmethoxy)allene; 1-Aza-1,3,4-trienes; 2-(Ferrocenylmethyl)-2-sulfanyl-1,2-dihydro-3H-pyrrol-3-ones; 3-(Ferrocenylmethoxy)-2-sulfanyl-1H-pyrroles; Isothiocyanates

Authors

Tarasova Ol'ga A. ¹ , Nedolya Nina A. ¹ , Albanov Alexander I. ¹ , Bagryanskaya Irina Yu. ² , Trofimov Boris A. ¹

Affiliations

1	A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1, Favorsky St., Irkutsk, 664033, Russian Federation
2	N. N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 9, Akad. Lavrentiev Ave., Novosibirsk, 630090, Russian Federation

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). © 2020

Tarasova O.A. , Nedolya N.A. , Albanov A.I. , Bagryanskaya I.Y. , Trofimov B.A.
Synthesis of pyrrole-ferrocene ensembles and their rearrangement into 2-(ferrocenylmethyl)-1,2-dihydro-3H-pyrrol-3-ones
Journal of Organometallic Chemistry. 2021. V.933. 121651 . DOI: 10.1016/j.jorganchem.2020.121651 WOS Scopus РИНЦ

Published print:

Feb 1, 2021

Web of science	WOS:000608413800008
Scopus	2-s2.0-85098470155
Elibrary	45045906
OpenAlex	W3110946654