N-Aryl/HetAryl-4,5-unsubstituted pyrroles were synthesized from Ar/HetAr-amines, 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… Click to show full abstract
N-Aryl/HetAryl-4,5-unsubstituted pyrroles were synthesized from Ar/HetAr-amines, 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-Aryl/HetAryl-4,5-unsubstituted pyrrole scaffolds, which can be further derived to access multi-substituted pyrrole-3-carboxamides. In the presence of 1.2 equiv. of KI, polysubstituted pyrazolo[3,4-b]pyridine derivative was also successfully synthesized.
Journal Title: Beilstein Journal of Organic Chemistry
Year Published: 2020
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