1,5,7‐Triazabicyclo[4.4.0]dec‐5‐ene (TBD): An Organocatalyst for Rapid Access to 3‐Hydroxyisoindolin‐1‐ones

The bicyclic guanidine 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) was used as a catalyst to develop a method for the synthesis of 3-hydroxyisoindolin-1-ones from 3-alkylidenephthalides and amines. This method provides a rapid and more sustainable option with broad scope for the synthesis of such scaffolds.

Abstract

The readily available organocatalyst 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) was used for the rapid synthesis of 3-hydroxyisoindolin-1-ones from 3-alkylidenephthalides. The transformation occurs at room temperature and requires less solvent than traditional methods, providing a more sustainable synthetic option to access 3-hydroxyisoindolin-1-ones with broad scope. Elaboration of the products to diverse scaffolds as well as synthesis of biologically active compounds are demonstrated.

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