Diastereoselective Synthesis of CF3-Pyrano[3,4-c]quinolones from Hetero-Dendralenes and Aldehydes

被引：1
|
作者：
Nagababu, Chavakula [1 ,2 ]
Sainadh, Srirangam [1 ,2 ]
Desagoni, Madhu [1 ,2 ]
Nanubolu, Jagadeesh Babu [2 ,3 ]
Punna, Nagender [1 ,2 ]
机构：
[1] Indian Inst Chem Technol CSIR IICT, Fluoro Agro Chem Div, CSIR, Hyderabad 500007, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
[3] Indian Inst Chem Technol CSIR IICT, Analyt Dept, CSIR, Hyderabad 500007, India
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 16期
关键词：
Pyrano[3,4-c]quinolone; Hetero-dendralene; Oxa-Diels-alder reaction; Cross-conjugated enolate; DIELS-ALDER REACTION; ONE-POT SYNTHESIS; DIENE; INHIBITORS;
D O I：
10.1002/adsc.202400335
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Herein, we demonstrate an Oxa-Diels-Alder reaction of 3-trifluoroacetyl-4-methyl-quinolin-2(1H)-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 CF3-group is responsible for making the methyl group present in quinolone moiety more acidic to furnish the corresponding hetero dendralene intermediate.
引用
收藏
页码：3438 / 3442
页数：5
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