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 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 amine deprotection 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.

Abstract

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.

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