Abstract
The reaction of equimolar amounts of propyne iminium trifluoromethanesulfonates 1a, b and isoquinoline yielded, after hydrolytic work-up, the N-(3-oxoprop-1-en-1-yl)isoquinolinium salts 4a, b in modest yields. Monitoring of the reaction by 1H NMR spectroscopy indicated the formation of salts 4, 3-isoquinolinio-substituted propene iminium salts 3, and N,N,N',N'-tetramethylvinamidinium salts 5 as the major components. The expected aminoallenes (2-(3-(dimethylamino)allen-1- yl)isoquinolinium triflates) 2 could not be detected in the reaction solutions. It is possible, however, to trap the aminoallene intermediates in a polar [4+2] cycloaddition reaction, as shown by the isolation of 2 : 1 adducts 7c, d in good yield from cyclopropyl-substituted propyne iminium triflates 1c, d and isoquinoline. Hydride abstraction from 7c, d yielded the 2,4-dicyclopropyl-1,3- bis((dimethyliminio)(aryl)methyl)pyrido[2,1-a]isoquinolinium tris(triflates) 8c, d.
Sign-in/Register to access full text options 
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.
