Optimized Conditions for Passerini-Smiles Reactions and Applications to Benzoxazinone Syntheses

Abstract

Initial conditions disclosed for the Passerini-Smiles reaction are associated with a lack of efficiency that has prevented chemists from using it since its discovery. We wish to report herein our thorough study in the development of new experimental conditions for this coupling between electron-poor phenols, isocyanides, and carbonyl derivatives. These new conditions have been applied to several synthetic strategies towards benzoxazinones.

Keywords

• isocyanide
• Passerini-Smiles
• multicomponent reaction
• heterocycles
• benzoxazinones