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

摘要

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.