Year-end Sale % OFF 
Abstract
The thiopiperidone 1b , prepared from 1a (Lawesson's reagent, 85 %), underwent rapid reaction with allyl bromide to give the 5,6-dihydropyridinium salt 2c . By reaction of 2c with the appropriate Grignard reagents the C-2 functionalized intermediates 3c were obtained. Heating 3c (R = Pr) at 120°C in DME resulted in formation of the cyclized compounds 6 whereas in the presence of added propionic anhydride the thio-ester 7 was obtained. Under these latter conditions 3c (R = C 5H 11CH(OSiX)CC-) rearranged to give a mixture of 8 and 9 whereas in DME containing CH 3COOH-H 2O (trace) the desired 2,3-disubstituted 4-piperidones 11 and 12 were obtained in 95 % combined yield.
Published Version
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.
