A new entrant in ketene family: Generation of 2-(3-Oxo-allyl)-isoindole-1,3-dione and their [4+2] Cycloadditions with 1,3-Diazabuta-1,3-dienes

The manuscript describes a synthetic route for the formation of 5-(methylisoindole-1,3-dione) pyrimidinones by [4+2] cycloaddition reactions of functionalized 1,3-diazabuta-1,3-dienes with 2-(3-Oxo-allyl)-isoindole-1,3-dione generated in situ from phthaloylalanine and tosyl chloride using triethylamine as a base. The functionalized 5-(methylisoindole-1,3-dione) pyrimidinones were further explored in the deprotection of amines to afford a variety of 5-methylamino pyrimidinones. The synthesis of such functionalized pyrimidinones is significant as they have a wide range of pharmacological profiles and are valuable as organic synthons. Mechanistic insights are also proposed for the given synthetic methodology.

Automated summary

The manuscript presents a synthetic method for the formation of 5-(methylisoindole-1,3-dione) pyrimidinones. It involves the [4+2] cycloaddition reactions of functionalized 1,3-diazabuta-1,3-dienes with 2-(3-Oxo-allyl)-isoindole-1,3-dione generated in situ. The synthesized pyrimidinones have significant pharmaceutical profiles and can serve as valuable organic synthons. Mechanistic insights are also proposed.