A Short and Efficient Synthesis of 3-Diphenylphosphoryl- and 3-Diethoxyphosphoryl(aza)isoindolinones: Extension to the Sulfonylated Analogs

Axel Couture; Eric Deniau; Patrice Woisel; Pierre Grandclaudon

doi:10.1055/s-1997-1370

Synthesis 1997; 1997(12): 1439-1445
DOI: 10.1055/s-1997-1370

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A Short and Efficient Synthesis of 3-Diphenylphosphoryl- and 3-Diethoxyphosphoryl(aza)isoindolinones: Extension to the Sulfonylated Analogs

Axel Couture^* , Eric Deniau, Patrice Woisel, Pierre Grandclaudon

^*Laboratoire de Chimie Organique Physique, URA CNRS N° 351, Université des Sciences et Technologies de Lille, F-59655 Villeneuve d’Ascq Cédex, France, Fax +33(320)436561

Abstract

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A variety of 3-diphenylphosphoryl- and 3-diethoxyphosphoryl-(aza)isoindolinones have been efficiently prepared by aryne- and hetaryne-mediated cyclization of phosphorylated α-amino carbanions derived from suitably substituted 2- and 3-halobenamide and 3-chloropyridine-4-carboxamide derivatives. The synthesis of some 3-sulfonylated analogs by extension of this principle has been achieved.

phosphorylated α-amino carbanions - aryne-mediated cyclization - phosphorylated and sulfonylated (aza)isoindolinones

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