Abstract
AbstractThe nature and influence of the N‐sulfonyl group in aza‐Prins cyclization and the reactivity of the six‐membered aza‐cycle generated has been studied. The aza‐Prins cyclization of γ,δ‐unsaturated amines with a tosyl group at the nitrogen atom produces 2‐alkyl‐4‐halo‐1‐tosyl‐1,2,5,6‐tetrahydropyridines with a halovinyl function, extraordinarily stable to further derivatization and detosylation conditions. To modulate the reactivity of such aza‐cycles, a general study of the aza‐Prins cyclization reaction was performed with several sulfonamides. Ring formation occurs satisfactorily with both N‐nosyl and N‐mesylamines providing optimal conditions for further synthetic transformations. To exemplify the scope of this methodology, a short synthesis of the alkaloid coniine was successfully carried out.
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.
