PIDA/I-2-Mediated alpha- and beta-C(sp(3))-H Bond Dual Functionalization of Tertiary Amines
Zhu, Yu1,2; Shao, Li-Dong1; Deng, Zhen-Tao1,2; Bao, Ying1,2; Shi, Xin1,2; Zhao, Qn-Shi1
2018-09-07
发表期刊JOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
卷号83期号:17页码:10166-10174
摘要The alpha,beta-C(sp(3))-H bond dual functionalization of tertiary amines is still a challenging task for both organic and medicinal chemists. Herein a direct, mild, metal-free, and site-specific method mediated by PIDA/I-2 was developed for alpha,beta-C(sp(3))-H bond dual functionalization of tertiary amines, and this method can provide facile access to alpha-keto lactams or rarely studied alpha,alpha-diiodo lactams. Moreover, this method was used for the effective syntheses of three natural products [obscurumine C (13), obscurumine O (17), and strychnocarpine (18)] and direct preparation of mimics of the in vivo metabolites of two FDA-approved drugs (imatinib and donepezil) in 36-60% overall yield. The method represents a promising protocol for the late-stage alpha,beta-C(sp(3))-H bond oxidative dual functionalization of tertiary amine-containing drugs and complex natural products.
资助信息National Natural Science Foundation of China; National Basic Research Program (973 program) of China; Science and Technology Program of Yunnan Province; Youth Innovation Promotion Association CAS
DOI10.1021/acs.joc.8b01424
语种英语
资助项目National Natural Science Foundation of China[U1502223] ; National Natural Science Foundation of China[U0932602] ; National Natural Science Foundation of China[81603000] ; National Basic Research Program (973 program) of China[2011CB915503] ; Science and Technology Program of Yunnan Province[2017FB135] ; Youth Innovation Promotion Association CAS
WOS研究方向Chemistry
WOS类目Chemistry, Organic
WOS记录号WOS:000444364600050
出版者AMER CHEMICAL SOC
引用统计
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/62415
专题植物化学与西部植物资源持续利用国家重点实验室
通讯作者Zhao, Qn-Shi
作者单位1.Chinese Acad Sci, State Key Lab Phytochem & Plant Resources West Ch, Kunming Inst Bot, Kunming 650201, Yunnan, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
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Zhu, Yu,Shao, Li-Dong,Deng, Zhen-Tao,et al. PIDA/I-2-Mediated alpha- and beta-C(sp(3))-H Bond Dual Functionalization of Tertiary Amines[J]. JOURNAL OF ORGANIC CHEMISTRY,2018,83(17):10166-10174.
APA Zhu, Yu,Shao, Li-Dong,Deng, Zhen-Tao,Bao, Ying,Shi, Xin,&Zhao, Qn-Shi.(2018).PIDA/I-2-Mediated alpha- and beta-C(sp(3))-H Bond Dual Functionalization of Tertiary Amines.JOURNAL OF ORGANIC CHEMISTRY,83(17),10166-10174.
MLA Zhu, Yu,et al."PIDA/I-2-Mediated alpha- and beta-C(sp(3))-H Bond Dual Functionalization of Tertiary Amines".JOURNAL OF ORGANIC CHEMISTRY 83.17(2018):10166-10174.
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