Synthesis of Functionalized Benzo[g]indoles and 1-Naphthols via Carbon–Carbon Triple Bond Breaking/Rearranging,Organic Letters

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Synthesis of Functionalized Benzo[g]indoles and 1-Naphthols via Carbon–Carbon Triple Bond Breaking/Rearranging
Organic Letters ( IF 4.9 ) Pub Date : 2017-11-30 00:00:00 , DOI: 10.1021/acs.orglett.7b03410
Jia-Yin Wang ₁ , Peng Zhou _{1,

2} , Guigen Li _{2,

3} , Wen-Juan Hao ₁ , Shu-Jiang Tu ₁ , Bo Jiang ₁

Affiliation

Novel carbon–carbon triple bond breaking and rearranging reactions of benzene-linked allene–ynes have been established. The reactions can be selectively controlled toward the formation of two families of skeletally diverse benzo[g]indoles and 1-naphthols under mild conditions. Silver salt was found to efficiently promote indole annulation to give multifunctional benzo[g]indoles with the installation of two sulfonyl groups into the indole ring via N–S and N–F bond cleavage of NFSI, whereas NBS and NCS-mediated benzannulations occurred with the formation of dihalogenated 1-naphthols.

中文翻译：

碳-碳三键断裂/重排合成功能化苯并[ g ]吲哚和1-萘酚

已经建立了苯连接的烯-炔的新型碳-碳三键断裂和重排反应。在温和的条件下，可以选择性地控制反应，以形成两个不同骨架的苯并[ g ]吲哚和1-萘酚。发现银盐可有效促进吲哚环化，并通过NFSI的N–S和N–F键裂解，在吲哚环中安装两个磺酰基，从而形成多功能的苯并[ g ]吲哚，而NBS和NCS介导的苯环发生在二卤代1-萘酚的形成。

更新日期：2017-11-30

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