Chemistry of Phosphorus Ylides. Part 36 Reactions of 2-Hydroxyisoindole-, Isoindoline-, and Indane-1,3-Dione With Stable and Active Phosphonium Ylides

Abstract

The stabilized alkylidenephosphoranes namely, acetyl-, benzoyl-, methoxycarbonyl-, and ethoxycarbonyl-methylenetriphenylphosphorane react with 2-hydroxyisoindole-1,3-(2H)dione to give the corresponding isoindoline-ylidenes, along with triphenylphosphane oxide. On the other hand, the reaction of active phosphacumulenes, (N-phenyliminovinylidene)-, and (2-oxovinylidene)-triphenylphosphorane with hydroxyisoindole-, isoindoline-, and indane-1,3-dione afforded phosphanylidenecyclobutylidenes derivatives, together with triphenylphosphane oxide. Mechanisms accounting for the formation of the new products are discussed. The antimicrobial activities for the new compounds are also reported.

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GRAPHICAL ABSTRACT

Keywords:

• Isoindolinones
• stable phosphonium ylides
• phosphacumulenes
• phosphanylidenecyclobutylidene derivatives
• antimicrobial activities