Syntheses of Pyrrolo- and Indoloisoquinolinones by Intramolecular Cyclizations of 1-(2-Arylethyl)-5-benzotriazolylpyrrolidin-2-ones and 3-Benzotriazolyl-2-(2-arylethyl)-1-isoindolinones

Abstract

1,5,6,10b-Tetrahydropyrrolo[2,1-alpha]isoquinolin-3(2H)-ones 17a,b, 17d,e, and 5,12b-dihydroisoindolo[1,2-alpha]isoquinolin-8(6H)-ones 22a-e were prepared by intramolecular cyclizations of 1-(2-arylethyl)-5-benzotriazolyl-pyrrolidin-2-ones 15a,b, 15d,e, and 3-benzotriazolyl-2-(2-arylethyl)-1-isoindolinones 20a-e, respectively, in the presence of titanium chloride. Products from chiral amines were obtained with stereoselectivities of > or = 94%.