Intramolecular cycloadditions with 1-aminoisobenzofurans: a simple entry into the field of polycyclic aza-compounds

Abstract

Starting with 6-methoxyisochromane-1,3-dione (1) isobenzofuran 5 was generated in situ using the Hamaguchi–Ibata methodology. Intramolecular cycloaddition with subsequent transformations provides benzo[h]quinolines of type 7, 8 and 9. In a similar manner 11-azasteroid analogues (22–26) were obtained, starting with 1 and amine 18. Density functional theoretical (DFT) studies of various inter- and intramolecular Diels–Alder reactions are reported.