64302-87-0Relevant academic research and scientific papers
REDUCTIVE CLAISEN REARRANGEMENTS OF ANTHRAQUINONE ALLYL ETHERS
Boddy, Ian K.,Boniface, Peter J.,Cambie, Richard C.,Craw, Peter A.,Larsen, David S.,et al.
, p. 4407 - 4408 (1982)
Gentle heating of allyloxyanthraquinones with sodium dithionite in dimethylformamide - water effects a rapid and controlled rearrangement to give high yields of 2-allylanthraquinones.
Efficient reductive Claisen rearrangement of prop-2’-enyloxyanthraquinones and 2’-chloroprop-2’-enyloxyanthraquinones with iron powder in ionic liquids
Nadali, Samaneh,Khoshroo, Ali,Aghapour, Ghasem
, p. 883 - 895 (2018/06/07)
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]BF4 (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.
Caged trans-4-hydroxy-2-nonenal
Brinson, Robert G.,Jones, Paul B.
, p. 3767 - 3770 (2007/10/03)
(Chemical Equation Presented) A caged 4-hydroxy-2-nonenal (4-HNE) has been prepared and its photochemistry investigated. Upon photolysis, 1 releases 4-HNE in up to 100% yield. From these photolyses, 4-HNE could be isolated in up to 91% yield. 4-HNE is produced under either aerobic or anaerobic conditions. The caging strategy does not require prior preparation of 4-HNE and, therefore, represents a three-step synthetic route to the bioactive enal in 48% overall yield.
Experiments Directed Towards the Synthesis of Anthracyclinones. VIII. Functionalization of Hydroxyanthraquinones by Reductive Claisen Rearrangements
Boddy, Ian K.,Boniface, Peter J.,Cambie, Richard C.,Craw, Peter A.,Huang, Zhen-Dong,et al.
, p. 1511 - 1529 (2007/10/02)
Gentle heating of allyloxyanthraquinones with sodium dithionite in dimethylformamide/water effects a rapid and controlled rearrangement to give high yields of 2-allylhydroxyanthraquinones.Starting from quinizarin, key intermediates for two synthetic routes to 4-demethoxydaunomycinone have been prepared from products by means of two such reductive Claisen rearrangements.
