Abstract
A one-pot, metal-free, double cyclization for the synthesis of bicyclic 2-pyridones as peptidomimetics was developed. In this process, the transformation of 2-pyrones bearing a tethered, homochiral α-amino acid started with the removal of the N-Boc protective group under acidic or neutral conditions at elevated temperature, followed by several key transformations, including cyclic enamine formation, decarboxylation or esterification, isomerization, and lactamization, to furnish bicyclic 2-pyridones in up to 98% yield with retention of the chirality at the α-carbon of the amino acid portion of the molecule. Exploration of the substrate scope revealed some selectivity between the decarboxylation and esterification pathways under thermal acidic conditions, while performing the reaction in boiling water yielded the decarboxylation products exclusively.
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.
