Abstract
Iminophosphoranes 4, derived from ethyl alpha-azido-2-(allyloxy)-3-methoxycinnamates, react with ketenes to give the corresponding ketene imines, which by thermal treatment at 150-160-degrees-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 fluoreno[2,3,4-ij]isoquinolines 9 in moderate yields. Similarly, iminophosphoranes 14 derived from ethyl alpha-azido-2,3-disubstituted-4-(allyloxy)cinnamates reacted with diphenyl ketene to give the intermediate ketene imines, which at 150-160-degrees-C undergo a cascade of pericyclic reactions to give the isoquinolines 15 and the pentacyclic compounds 16 in moderate yields.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
