Catalyst-free and atom-economic synthesis of substituted 1-acetyl and 1-hydroxyl carbazoles

The first-ever Diels-Alder reactions of 3-alkenyl indoles with a conjugated alkynyl ketone are reported. These reactions proceed in an atom-economic manner without a catalyst and give various substituted 1-acetyl carbazoles in moderate to excellent yields. These products can be converted to 1-hydrox...

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Bibliographic Details
Published in:Tetrahedron 2018-04, Vol.74 (15), p.1965-1972
Main Authors: Yu, Feng, Li, Dan, Wei, Yu, Kang, Rui-Ming, Guo, Qi-Xiang
Format: Article
Language:English
Subjects:
3-Alkenyl indole
Atom-economic
Carbazole
Catalyst-free
Diels-Alder
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Summary:The first-ever Diels-Alder reactions of 3-alkenyl indoles with a conjugated alkynyl ketone are reported. These reactions proceed in an atom-economic manner without a catalyst and give various substituted 1-acetyl carbazoles in moderate to excellent yields. These products can be converted to 1-hydroxyl carbazoles in high yields under mild reaction conditions. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.02.066