Post-Ugi carbocyclization/fragmentation sequence for the synthesis of 6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones

被引：18
|
作者：
Tran Thi Thu Trang [1 ,2 ]
Peshkov, Anatoly A. [1 ]
Jacobs, Jeroen [3 ]
Van Meervelt, Luc [3 ]
Peshkov, Vsevolod A. [4 ]
Van der Eycken, Erik V. [1 ]
机构：
[1] Univ Leuven KU Leuven, Dept Chem, Lab Organ & Microwave Assisted Chem, B-3001 Louvain, Belgium
[2] Hanoi Natl Univ Educ, Hanoi, Vietnam
[3] Univ Leuven KU Leuven, Dept Chem, Biomol Architecture, B-3001 Louvain, Belgium
[4] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 22期
关键词：
Ugi reaction; Cyclization; 6,7-Dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones; Aerobic oxidation; MULTICOMPONENT REACTIONS;
D O I：
10.1016/j.tetlet.2015.03.092
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A two-step one-pot sequence, involving Ugi reaction followed by base-promoted carbocyclization accompanied by cleavage of the isocyanide-originated amide moiety, has been successfully elaborated in order to provide a fast access to 6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones. When the cyclizations were run under air atmosphere a subsequent oxidation occurred producing oxidized 7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2882 / 2886
页数：5
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