Annulated isoxazoles via [3 + 2] cycloaddition of alkenyl bromides and oximoyl chlorides and Ag(I) promoted elimination.

Abstract

Substituted salicylaldehydes are converted to fused tetracyclic isoxazoles through a synthetic sequence incorporating substitution of 2-bromo-2-cyclohexen-1-ol, formation of an oxime function, conversion to an oximoyl chloride, intramolecular [3 + 2] cycloaddition, and elimination of an equivalent of hydrogen bromide using silver(I) carbonate. Six examples of this sequence are presented.

DOI: 10.1021/jo501376q

Cite this paper

@article{CastilloContreras2014AnnulatedIV, title={Annulated isoxazoles via [3 + 2] cycloaddition of alkenyl bromides and oximoyl chlorides and Ag(I) promoted elimination.}, author={Emmanuel B Castillo-Contreras and Alexander M. Stahl and Gregory R Dake}, journal={The Journal of organic chemistry}, year={2014}, volume={79 15}, pages={7250-5} }