A copper-catalyzed tandem reaction for the construction of coumarin fused 9H-pyrrolo[1, 2-a]indoles. Issue 41 (9th October 2017)

• Record Type: Journal Article
• Authors: Jin, Shao-Jing; Guo, Jiao-Mei; Zhu, Yan-Shuo; Wang, Qi-Lin; Bu, Zhan-Wei
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 41(2017)
• Page Start: 8729
• Page End: 8737
• Publication Date: 2017-10-09
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob02307c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An efficient copper-catalyzed Friedel–Crafts alkylation/cyclization/isomerization sequence of 3-arylcarbonyl coumarins and 3-methyl indole was developed to afford a wide range of functionalized coumarin fused 9 H -pyrrolo[1, 2- a ]indoles with a 6-6-5-5-6 pentacyclic core. Abstract : An efficient copper-catalyzed Friedel–Crafts alkylation/cyclization/isomerization sequence of 3-arylcarbonyl coumarins and 3-methyl indole was developed to afford a wide range of functionalized coumarin fused 9 H -pyrrolo[1, 2- a ]indoles, which feature a 6-6-5-5-6 pentacyclic core, in 34–99% yields. Moreover, gram-scale experiment and chemical transformations were conducted to demonstrate the synthetic value of this protocol.