Three-component reactions of aromatic amines, 1,3-dicarbonyl compounds, and alpha-bromoacetaldehyde acetal to access N-(hetero)aryl-4,5-unsubstituted pyrroles
文献类型： 外文期刊
作者： Huang, Wenbo 1 ; Wang, Kaimei 1 ; Liu, Ping 2 ; Li, Minghao 3 ; Ke, Shaoyong 1 ; Gu, Yanlong 2 ;
作者机构： 1.Hubei Acad Agr Sci, Natl Biopesticide Engn Res Ctr, Hubei Biopesticide Engn Res Ctr, 8 Nanhu Ave, Wuhan 430064, Peoples R China
2.Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi City 832004, Peoples R China
3.Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Hubei Key Lab Mat Chem & Serv Failure, Key Lab Mat Chem Energy Convers & Storage,Minist, 1037 Luoyu Rd, Wuhan 430074, Peoples R China
关键词： acid catalyst; [1+2+2] annulation; KI; pyrazolo[3,4-b]pyridine; pyrroles
期刊名称：BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY （ 2020影响因子：2.883； 五年影响因子：2.785 ）
ISSN： 1860-5397
年卷期： 2020 年 16 卷
收录情况： SCI
摘要： N-(Hetero)aryl-4,5-unsubstituted pyrroles were synthesized from (hetero)arylamines, 1,3-dicarbonyl compounds, and alpha-bromoacetaldehyde acetal by using aluminum(III) chloride as a Lewis acid catalyst through [1 + 2 + 2] annulation. This new versatile methodology provides a wide scope for the synthesis of different functional N-(hetero)aryl-4,5-unsubstituted pyrrole scaffolds, which can be further derived to access multisubstituted pyrrole-3-carboxamides. In the presence of 1.2 equiv of KI, a polysubstituted pyrazolo[3,4-b]pyridine derivative was also successfully synthesized.
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