Claisen rearrangement of allyloxyanthraquinones

SYNTHESIS OF 2-PROPYLANTHRALIN AND 2,7-DIPROPY LANTHRALIN VIA REDUCTIVE CLAISEN REARRANGEMENT OF ALLYLOXYANTHRAQUINONES

Reductive Claisen rearrangement of 1-allyloxy-8-methoxy-9, 10-anthraquinone followed by demethylation and reduction, and of 1,8-bisallyloxy-9,lO-anthraquinone followed by reduction provides regiospecific syntheses of 2-propyl- and 2,7-dipropyl anthralin

The Claisen Rearrangement

Microwave accelerated aza-Claisen rearrangement.

A study of microwave-induced and standard thermal Overman rearrangement of selected allylic trichloroacetimidates 1a-1f, 6-8 to the corresponding acetamides 2a-2f, 9-11 is reported. The microwave-assisted rearrangement of trifluoroacetimidate 13 is also described. Using this methodology, an efficient access to versatile allylic trihaloacetamides building synthons was established.

The tandem intermolecular hydroalkoxylation/Claisen rearrangement.

The Au(I)-catalyzed intermolecular hydroalkoxylation of alkynes with allylic alcohols to provide allyl vinyl ethers that subsequently undergo Claisen rearrangement is reported. This new cascade reaction strategy facilitates the direct formation of γ,δ-unsaturated ketones from simple starting materials in a single step.

Recent developments in the Reformatsky-Claisen rearrangement.

The rearrangement of allyl a-bromoacetates with Zn dust is known as the Reformatsky-Claisen rearrangement. Whereas the Ireland-Claisen rearrangement has been widely used in the synthesis of a diverse range of natural products, the Zn-mediated Reformatsky-Claisen rearrangement has not been utilized so often. In this article, we will provide an overview of recent advances in the Reformatsky-Clais...