Synthesis of naphthyridin-2(1H)-one derivatives via ring expansion of 3-substituted-1H-pyrrolo[2,3-b]pyridin-2(3H)-one derivatives

被引:9
作者
Croix, C. [1 ,2 ]
Massip, S. [3 ]
Viaud-Massuard, M. -C. [1 ,2 ]
机构
[1] Univ Tours, UFR Sci Pharmaceut, Grp Innovat & Ciblage Cellulaire, 31 Ave Monge, F-37200 Tours, France
[2] Univ Tours, UFR Sci Pharmaceut, Equipe Innovat Mol & Therapeut 4, 31 Ave Monge, F-37200 Tours, France
[3] Univ Bordeaux, CNRS, Inst Europeen Chim & Biol, UMS 3033,INSERM US 001, 2 Rue Robert Escarpit, F-33607 Pessac, France
关键词
ANTITUMOR-ACTIVITY; ANTICANCER AGENTS; INHIBITOR; ALKALOIDS; CAMPTOTHECIN; 7-AZAINDOLE; DISCOVERY; ANALOGS; DESIGN;
D O I
10.1039/c8cc01518j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reaction of 3-substituted 1H-pyrrolo[2,3-b]pyridin-2(3H)-one derivatives with sodium azide or azidotrimethylsilane under microwave irradiation provided 3-and 4-amino-naphthyridin-2(1H)-one derivatives through cycloaddition-ring expansion. The insertion of the azide into the alpha,beta unsaturated carbonyl of 3-substituted pyrrolo[2,3-b] pyridin-2(3H)-one derivatives proceeded via an unusual rearrangement. This methodology provided 39 ring expansion examples in moderate to good yields.
引用
收藏
页码:5538 / 5541
页数:4
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