Base Promoted Synthesis of 4‐Quinolones Fused with Medium‐Sized Rings

In the presence of cesium carbonate, ynones bearing an ortho‐amino group reacted with cyclic β‐ketoesters through conjugated addition/carbon‐carbon σ‐bond cleavage/nucleophilic aromatic substitution tandem reaction to obtain 4‐quinolones fused with medium‐sized rings in good yields. This is the firs...

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Bibliographic Details
Published in:European journal of organic chemistry 2023-12, Vol.26 (46), p.n/a
Main Authors: Wang, Mengdan, Ma, Junying, Wang, Junling, Lu, Weiwei, Pan, Bingli
Format: Article
Language:English
Subjects:
4-quinolones
Carbon
Cascade chemical reactions
Cesium
insertion reaction
medium-sized rings
mild reaction conditions
Substitution reactions
Synthesis
transition-metal-free
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Summary:In the presence of cesium carbonate, ynones bearing an ortho‐amino group reacted with cyclic β‐ketoesters through conjugated addition/carbon‐carbon σ‐bond cleavage/nucleophilic aromatic substitution tandem reaction to obtain 4‐quinolones fused with medium‐sized rings in good yields. This is the first example of synthesis of 4‐quinolones through base‐promoted insertion reactions of carbon‐carbon triple bonds into carbon‐carbon σ‐bonds. Notable features of this program are mild and transition‐metal‐free reaction conditions. An efficient and simple protocol for the synthesis of 4‐quinolone derivatives via base‐promoted carbon‐carbon σ‐bond cleavage reaction of cyclic β‐ketoesters under mild reaction conditions has been developed.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202300519