129199-79-7Relevant academic research and scientific papers
Domino Reactions. One-Pot Preparation of Fluorenoisoquinoline Derivatives from Conjugated Ketene Imines
Molina, Pedro,Alajarin, Mateo,Vidal, Angel,Fenau-Dupont, J.,Declerq, J. P.
, p. 4008 - 4016 (2007/10/02)
Iminophosphoranes 4, derived from ethyl α-azido-2-(allyloxy)-3-methoxycinnamates, react with ketenes to give the corresponding ketene imines, which by thermal treatment at 150-160 deg C undergo a consecutive electrocyclic ring closure/Claisen rearrangement/second ring closure/double aromatization process to give isoquinoline derivatives 7 and/or the previously unknown fluorenoisoquinolines 9 in moderate yields.Similarly, iminophosphoranes 14 derived from ethyl α-azido-2,3-disubstituted-4-(allyloxy)cinnamates reacted with diphenyl ketene to give the intermediate ketene imines, which at 150-160 deg C undergo a cascade of pericyclic reactions to give the isoquinolines 15 and the pentacyclic compounds 16 in moderate yields.
One-pot Preparation of Derivatives of the Unknown Fluorenoisoquinoline Ring from Conjugated Ketenimines by a Consecutive Electrocyclic Ring-closure/Claisen Rearrangement/Intramolecular Diels-Alder Cycloaddition/Double Aromatization Process
Molina, Pedro,Alajarin, Mateo,Vidal, Angel,Feneau-Dupont, J.,Declercq, J. P.
, p. 829 - 831 (2007/10/02)
A short synthesis of fluorenoisoquinoline derivatives (8) based on a new method of three consecutive annelations which involves thermal cyclization of conjugated ketenimines is described; the crystal structure of (8) has been determined.
