Access to 2,3-Fused Pyrroles via Visible Light Driven Coupling of α-Azidochalcones with 1/2-Naphthols, or 2-Hydroxy-1,4-Naphthoquinone

被引：35

作者：

Borra, Satheesh ^{[1
,2
]}

Chandrasekhar, D. ^{[1
,2
]}

Newar, Uma Devi ^{[1
]}

Maurya, Ram Awatar ^{[1
,2
]}

机构：

[1] NEIST, CSIR, Chem Sci & Technol Div, Appl Organ Chem Grp, Jorhat 785006, Assam, India

[2] NEIST, CSIR, Acad Sci & Innovat Res AcSIR, Jorhat 785006, Assam, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 02期

关键词：

ONE-POT SYNTHESIS; VINYL AZIDES; PHOTOREDOX CATALYSIS; CHEMICAL-SYNTHESIS; FUNCTIONALIZATION; DERIVATIVES; PRECURSORS;

D O I：

10.1021/acs.joc.8b02459

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Azidochalcones were coupled with 1/2-naphthols or 2-hydroxy-1,4-naphthoquinone using Ru(bpy)(3)(PF6)(2) as a photocatalyst under blue LED light irradiation to yield 2,3-fused pyrroles in high yields (68-84%). The overall transformation involves photosensitized decomposition of alpha-azidochalcones into highly reactive 2H-azirines which are trapped by 1/2-naphthols or 2-hydroxy-1,4-naphthoquinone, leading to the construction of two new C-N and one new C-C bonds.

引用

页码：1042 / 1052

页数：11

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