Rh(III) and Ru(II)-Catalyzed Site-Selective C-H Alkynylation of Quinolones

被引：70
|
作者：
Kang, Dahye [1 ,2 ]
Hong, Sungwoo [1 ,2 ]
机构：
[1] Korea Adv Inst Sci & Technol, Dept Chem, Taejon 305701, South Korea
[2] Inst for Basic Sci Korea, Ctr Catalyt Hydrocarbon Functionalizat, Taejon 305701, South Korea
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 08期
关键词：
INHIBITORS; INDOLES; ARENES; GOLD; HETEROCYCLES; THIOPHENES; SCAFFOLD; ALPHA;
D O I：
10.1021/acs.orglett.5b00641
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
C2- and C5-alkynylated quinolone scaffolds are core structures of numerous biologically active molecules. Utilizing TIPS-EBX as an alkynylating agent, we have developed an efficient and site-selective C5 alkynylation of 4-quinolones that is directed by the weakly coordinating carbonyl group. In addition, Ru(II) catalyzed C2-selective alkynylation was successfully realized via N-pyrimidyl group-directed cross-couplings to access valuable C2-alkynylated 4-quinolones. This strategy provides direct access to the C2 or C5 alkynylated 4-quinolones. Furthermore, the reaction was applied to isoquinolones for C3-selective alkynylation.
引用
收藏
页码：1938 / 1941
页数：4
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