Synthesis of δ- and α-Carbolines via Nickel-Catalyzed [2+2+2] Cycloaddition of Functionalized Alkyne-Nitriles with Alkynes

被引：72
作者：
Wang, Gaonan [1 ]
You, Xu [1 ]
Gan, Yi [1 ]
Liu, Yuanhong [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 01期
基金：
中国国家自然科学基金;
关键词：
LEWIS-ACIDS; CYCLIZATION; PYRIDINES; 2-AMINOPYRIDINES; HETEROCYCLES; CYANAMIDES; INHIBITION; DISCOVERY; DIYNES; ROUTE;
D O I：
10.1021/acs.orglett.6b03385
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new method for the synthesis of delta- and alpha carbolines through Ni-catalyzed [2 + 2 + 2] cycloaddition of ynamide-nitriles or alkyne-cyanamides with alkynes has been developed. The catalytic system of NiCl2(DME)/dppp/Zn with a low-cost Ni(II)-precursor was first utilized in Ni-catalyzed [2 + 2 + 2] cycloaddition reactions, and the in situ generated Lewis acid may play an important role for the successful transformation. Not only internal alkynes but also terminal alkynes undergo the desired cycloaddition reactions efficiently to furnish the carboline derivatives with wide diversity and functional group tolerance.
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收藏
页码：110 / 113
页数：4
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