期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 24, 页码 11863-11872出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo500807d
关键词
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资金
- National Natural Science Foundation of China [21372013]
- National Basic Research Program of China [2010CB833201, 2012CB722602]
- Shenzhen Peacock Program [KQTD201103]
- Shenzhen Technology Innovation Program [CXZZ20130517152257071]
Indole-containing polyaromatic scaffolds are widely found in natural products, pharmaceutical agents, and p-conjugated functional materials. Often, the synthesis of these highly valuable molecules requires a multistep sequence. Therefore, a simple, one-step protocol to access libraries of polyaromatic indole scaffolds is highly desirable. Herein we describe the direct synthesis of polysubstituted indolo[2,1-alpha]isoquinoline analogues via a double CH annulation cascade using triazene as an internally cleavable directing group. Evidence from HRMS and theoretical calculations suggests that an unprecedented 1,2-alkyl migration might be responsible for the in situ cleavage of the directing group. Both kinetic isotope effects and DFT calculations suggested that the alkyne insertion step is rate-limiting for the second C,N annulation reaction.
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