Domino reactions of cyclic enaminones leading to selective synthesis of pentacyclic indoles and its functionalization

TETRAHEDRON

卷:72

Article

Fan, Wei¹  Li, Yan-Rong¹  Li, Qun¹  Jiang, Bo^2,3  Li, Guigen^1,2 

[1] Nanjing Univ, Inst Chem & BioMed Sci, Nanjing 210093, Jiangsu, Peoples R China

[2] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

[3] Jiangsu Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Jiangsu, Peoples R China

关键词: Multicomponent domino reactions (MDRs);    Fused indoles;    Allylic hydroxylation;    Esterification;    Group-assisted purification (GAP) chemistry;   

DOI  :  10.1016/j.tet.2016.06.058

来源: Elsevier

【 摘 要 】

A new multicomponent domino reaction of cyclic enaminones with acenaphthylene-1,2-dione in an anhydride solvent has been established, providing selective protocol to pentacyclic indoles with different substituted patterns (up to 50 examples). Both substitutions on the cyclic enaminone ring and reaction temperatures showed obvious impact on the reaction pathways. For instance, selective allylic hydroxylation and allylic esterification of in situ generated indoles depend on reaction temperatures. With special substituents, the reactions underwent dehydrogenation process to give access to different substituted fused indoles with good to excellent yields. These reactions feature mild conditions, convenient one-pot operation and short reaction times. The purification of products only needs to be washed by 95% ethanol without traditional chromatography and recrystallization, which characterizes group assisted purification (GAP) chemistry. (C) 2016 Published by Elsevier Ltd.

【 授权许可】

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