Diastereoselective Synthesis of CF 3 ‐Pyrano[3,4‐ c ]quinolones from Hetero‐Dendralenes and Aldehydes

Herein, we demonstrate an Oxa‐Diels‐Alder reaction of 3‐trifluoroacetyl‐4‐methyl‐quinolin‐2(1 H )‐one with aldehydes in the presence of a base to engineer the functionalized pyrano[3,4‐ c ]quinolones. This reaction proceeds through an in‐situ generated hetero dendralene intermediate and features per...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-08, Vol.366 (16), p.3438-3442
Main Authors: Nagababu, Chavakula, Sainadh, Srirangam, Desagoni, Madhu, Nanubolu, Jagadeesh Babu, Punna, Nagender
Format: Article
Language:English
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Summary:Herein, we demonstrate an Oxa‐Diels‐Alder reaction of 3‐trifluoroacetyl‐4‐methyl‐quinolin‐2(1 H )‐one with aldehydes in the presence of a base to engineer the functionalized pyrano[3,4‐ c ]quinolones. This reaction proceeds through an in‐situ generated hetero dendralene intermediate and features perfect stereoselectivity on a wide range of substrates with excellent atom economy. The high electron‐withdrawing nature of CF 3 ‐group is responsible for making the methyl group present in quinolone moiety more acidic to furnish the corresponding hetero dendralene intermediate.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400335