Synthesis of phthalimides from phthalonitriles and cyclic nitrone

February 26, 2024

• Title:       

  Synthesis of phthalimides from phthalonitriles and cyclic nitrone

• Image Source:

  Metal-free and PdII-promoted [2+3] cycloadditions of a cyclic nitrone to phthalonitriles: Syntheses of oxadiazolines as well as phthalamide-PdII and dihydropyrrolyl-iminoisoindolinone-Pd II complexes with high catalytic activity in suzuki-miyaura cross-coupling reactions

• Mark:

  Scheme 1

• Associated context:

  Hence, the reactions of 1a (R¹ =R² =R³ =R⁴ =H) and its methyl derivative  1b (R¹ =R² =R⁴ =H, R³ =CH₃₎ with the cyclic nitrone 2,  under the above conditions, give the phthalimide 3a and the  5-methyl derivative 3b, respectively, in moderate yields (ca.  50%) (Scheme 1). No reaction was observed at room temperature or under refluxing CHCl₃ at ambient pressure.