Thermal and Microwave-Assisted Synthesis of New Highly Functionalized Bis-β-lactams from Available Compounds via Bisketene as an Intermediate.

ABSTRACT: The synthesis of highly functionalized bis-β-lactams containing aromatic rings was achieved by thermal and microwave-assisted methods starting from easily available 2-(4-hydroxyphenyl)acetic acid and 2,2'-(propane-2,2-diyl)diphenol precursors. The approach to these valuable heterocyclic scaffolds involved formal [2π + 2π] cycloadditions between Schiff bases and novel bisketenes, which were generated in situ, followed by an electrocyclic reaction of zwitterionic intermediates. Reactions carried out under microwave irradiation were clean and gave high yields with significantly reduced reaction times. Interestingly, in the thermal method, the reaction proceeded in a stereospecific manner, and only the trans-cis or cis-cis isomers were formed. However, under the microwave conditi

SUBMITTER: Nadiki HH 

PROVIDER: S-EPMC9494681 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature