An Efficient One-Pot Synthesis of Densely Functionalized Fused-Quinolines via Sequential Ugi4CC and Acid-Mediated Povarov-Type Reaction

被引：21
作者：
Ghoshal, Anirban [1 ,2 ]
Yugandhar, Doddapaneni [1 ,2 ]
Nanubolu, Jagadeesh Babu [3 ]
Srivastava, Ajay Kumar [1 ,2 ]
机构：
[1] CSIR, Indian Inst Chem Technol, Med Chem & Biotechnol Div, Hyderabad 500007, Andhra Prades, India
[2] Acad Sci & Innovat Res, Chem Sci Div, New Delhi 110025, India
[3] CSIR, Indian Inst Chem Technol, Ctr Xray Crystallog, Hyderabad 500007, Andhra Prades, India
来源：
ACS COMBINATORIAL SCIENCE | 2017年 / 19卷 / 09期
关键词：
post-Ugi functionalization; Ugi condensation; fused-quinoline; Povarov reaction; one-pot process; STEREOSELECTIVE TANDEM SYNTHESIS; TOPOISOMERASE-I INHIBITORS; SUBSTITUTED QUINOLINES; LUOTONIN-A; MULTICOMPONENT REACTIONS; BIOLOGICAL EVALUATION; ASYMMETRIC-SYNTHESIS; O-ALKYNYLALDEHYDES; NADH MODELS; DERIVATIVES;
D O I：
10.1021/acscombsci.7b00095
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A divergent synthesis of fused-quinolines has been explored by performing Ugi four-component condensation and sulfuric acid promoted deprotection/Povarov-type reaction in one-pot. The process involves Ugi condensation of propiolic acids, aldehydes/ketones, aminoaldehyde acetals and isocyanides followed by sulfuric acid promoted deprotection and Povarov-type reaction with anilines in ethanol. This method enables straightforward accss to the structurally diverse 2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-ones (DHPQ), 3,4-dihydrobenzo[b][1,6]naphthyridin-1(2H)-ones (DHBN), and 2,3,4,5-tetrahydro-1H-azepino[4,3-b]quinolin-1-ones (THAQ), starting from readily available starting materials.
引用
收藏
页码：600 / 608
页数：9
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