The halocyclization of functionalized alkynes is a useful approach for the construction of numerous heterocyclic scaffolds, many of which are known to be medicinally privileged. We have explored the iodocyclization of 2-(1-alkynyl)benzamides using a variety of reagents and reaction conditions. It was previously demonstrated that the n-BuLi or phosphazene superbase-mediated iodoaminocyclization leads to the formation of 3-methyleneisoindolin-1-ones (Z-isomers). Recently, we have observed that Trimethylsilyl trifluoromethanesulfonate-mediated iodocyclization of 2-(1-alkynyl)benzamides affords the E-isomers of the corresponding 3-methyleneisoindolin-1-ones stereoselectively. The scope of the methodology will be discussed.

Synthesis of 3-methyleneisoindolin-1-ones via Iodocyclization of 2-(1-alkynyl)benzamides

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.