119th General Meeting of the KCS

Type Oral Presentation
Area Oral Presentations of Young Scholars in Organic Division
Room No. 302호
Time THU 10:45-:
Code ORGN.O-8
Subject One-pot Synthesis of Quinolinones and Quinolinols through Cu-Catalyzed Aza-Michael Addition/Cyclization
Authors 강성일, 이윤미*
광운대학교 화학과, Korea
Abstract 2,3-Dihydro-4(1H)-quinolinones and 4-hydroxy-quinolines have been known to exhibit interesting biological properties such as BoNT/A LC inhibitors, analgesic and broad-spectrum antibiotic activity. Various methods have been developed, but there are some disadvantages to synthetic usability. For example, a long synthesis step is required and the reaction is carried out under harsh reaction conditions like high temperature and strong acid. Therefore, new synthetic approaches are still required. Inspired by our previous study involving Cu-catalyzed aza-Michael addition of anilines to phenyl vinyl sulfone to afford various β-amino sulfones with high efficiency, we developed an efficient and mild method for one-pot synthesis of 2,3-dihydro-4(1H)-quinolinone and 4-hydroxy-quinoline derivatives. One-pot synthesis is underwent via Cu-catalyzed aza-Michael addition of methyl 2-aminobenzoates to phenyl vinyl sulfones or vinyl ketones, followed by the treatment of in situ-generated β-amino groups with KOt-Bu to afford the cyclized products.
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