Synthesis of 1H-isoindoles by a novel rearrangement of some isoquinolin-4(1H)-ones

Abstract

The isoquinolinones 8 undergo acid-induced rearrangement to yield the isomeric 1,1-dihydro-3-aroylisoindoles 9 in good yield. The reaction involves hydrolysis of the CN bond to afford a putative intermediate amino diketone 10. Cyclization within this is controlled by two factors (i) the stability of the CN group in the starting material and product and (ii) the relative reactivity of the two carbonyl groups.