Lanthanide triiodide-catalyzed amination of phthalonitrile. The structure of 1-isopropylamino-3-(isopropylimino)isoindole.

Abstract  The reactions of phthalonitrile with MeNH2, PrnNH2, and PriNH2 in the presence of catalytic amounts of LnI3 (Ln = Nd or Dy) or LnI3(THF)3 (Ln = Gd or Nd) afford 1,3-bis(alkylimino)isoindolines (Alk = Me (1), Prn (2), or Pri (3), respectively). Under analogous conditions, 2-aminopyridine gives 1,3-bis(2-pyridylimino)isoindoline (4). The X-ray diffraction study of compound 3 showed that, in the crystalline state, this compound exists as the isomer, 1-isopropylamino-3-(isopropylimino)isoindole. [ABSTRACT FROM AUTHOR]