Abstract
A solid-phase organic synthesis method has been developed for the preparation of 3-carboxypyrrolinones 9. Treatment of polymer-bound malonic acid with amino alcohols afforded the malonamide resin products 6. Benzyl and alkyl amino alcohols were prepared in solution via a two-step procedure without purification and were coupled to the resin directly using a resin capture strategy. Polymer loadings and product conversions were determined by direct cleavage of resin-bound materials and analysis by 1H NMR spectroscopy with an internal standard. Treatment of the polymer-bound malonamides with TFA released the malonamic acids, 10, which underwent further reaction to afford the trifluoroacetate derivatives 11. Secondary amides underwent an additional cyclization to afford oxazoles 12. The malonamide resins 6 can be oxidized to the corresponding ketones 7 by treatment with CrO2(O-t-Bu)2, which can in turn be cyclized in the presence of LDA or LHMDS to afford the carboxypyrrolinones 8. TFA treatment releases the free carboxypyrrolinones, 9, in 43−80% overall yield.
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.
