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
收藏
页码：1042 / 1052
页数：11
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