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Three-component reactions of aromatic amines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal to access N-(hetero)aryl-4,5-unsubstituted pyrroles
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2020-11-30 , DOI: 10.3762/bjoc.16.241
Wenbo Huang 1 , Kaimei Wang 1 , Ping Liu 2 , Minghao Li 3 , Shaoyong Ke 1 , Yanlong Gu 2, 3
Affiliation  

N-(Hetero)aryl-4,5-unsubstituted pyrroles were synthesized from (hetero)arylamines, 1,3-dicarbonyl compounds, and α-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.

中文翻译:


芳香胺、1,3-二羰基化合物和α-溴乙醛缩醛的三组分反应生成N-(杂)芳基-4,5-未取代吡咯



以(杂)芳基胺、1,3-二羰基化合物和α-溴乙醛缩醛为原料,以氯化铝(III)为路易斯酸催化剂,通过[1 + 2]合成N- (杂)芳基-4,5-未取代吡咯。 + 2] 成环。这种新的多功能方法为合成不同功能的N- (杂)芳基-4,5-未取代的吡咯支架提供了广泛的范围,可以进一步衍生以获得多取代的吡咯-3-甲酰胺。在1.2当量KI存在下,还成功合成了多取代吡唑并[3,4- b ]吡啶衍生物。
更新日期:2020-12-01
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