Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 20, Pages 13141-13152Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01817
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- Alexander von Humboldt Foundation for the Linkage research Group program
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A sequential post-transformation of Ugi four-component reaction/nucleophilic substitution was developed for the synthesis of spiro-beta-lactam-pyrroloquinolines. This method involves the Ugi-4CR of 2-chloro-3-formyl quinolines 1a-h, amines 2a-d, 2-chloroacetic acid 3, and isocyanides 4a, 4b for the synthesis of versatile precursors 5a-v. The Ugi adducts were intramolecularly cyclized under basic conditions through the sequential nucleophilic aromatic substitution (SNAr)/second-order nucleophilic substitution (S(N)2) reaction to give spiro-beta-lactam-pyrroloquinoline scaffolds 6a-t. This approach is an efficient method for the synthesis of fused bioactive heterocyclic backbones containing quinoline, pyrrolidone, and beta-lactam with high bond-forming efficiency.
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