Efficient reductive Claisen rearrangement of prop-2'-enyloxyanthraquinones and 2'-chloroprop-2'-enyloxyanthraquinones with iron powder in ionic liquids

Authors

SAMANEH NADALI
ALI KHOSHROO
GHASEM AGHAPOUR

DOI

10.3906/kim-1711-49

Abstract

A rapid and selective iron-mediated reductive Claisen rearrangement of various prop-2'-enyloxyanthraquinones and 2'-chloroprop-2'-enyloxyanthraquinones to 1-hydroxy-2-(prop-2'-enyl)anthraquinones and anthrafurandiones is presented. All reactions are carried out in a mixture of ionic liquids, [Bzmim]Cl (1-benzyl-3-methylimidazolium chloride) and [Hmim]BF$_{4}$ (1-methylimidazolium tetrafluoroborate), in short reaction times (5-35 min). Our study showed that 1-(prop-2'-enyloxy)anthraquinone is more active than 1-(2'-chloroprop-2'-enyloxy)anthraquinone to perform this rearrangement.

Keywords

2'-Chloroprop-2'-enyloxyanthraquinone, anthrafurandione, Claisen rearrangement, iron, ionic liquid

First Page

883

Last Page

895

Recommended Citation

NADALI, SAMANEH; KHOSHROO, ALI; and AGHAPOUR, GHASEM (2018) "Efficient reductive Claisen rearrangement of prop-2'-enyloxyanthraquinones and 2'-chloroprop-2'-enyloxyanthraquinones with iron powder in ionic liquids," Turkish Journal of Chemistry: Vol. 42: No. 3, Article 22. https://doi.org/10.3906/kim-1711-49
Available at: https://journals.tubitak.gov.tr/chem/vol42/iss3/22