Three-Component Reactions of Aromatic Amines, 1,3-Dicarbonyl Compounds and α-Bromoacetaldehyde Acetal to Access N-Aryl/HetAryl-4,5-Unsubstituted Pyrroles

  1. Wenbo HuangORCID Logo,
  2. Kaimei Wang,
  3. Ping Liu,
  4. Shaoyong Ke and
  5. Yanlong Gu

Submitting author affiliation: National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Hongshan District, Wuhan, China

Beilstein Arch. 2020, 202094.

Published 25 Aug 2020

  • Preprint


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.

Keywords: Pyrroles; [1+ 2 + 2] Annulation; Acid catalyst; KI; Pyrazolo[3,4-b]pyridine

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Huang, W.; Wang, K.; Liu, P.; Ke, S.; Gu, Y. Beilstein Arch. 2020, 202094. doi:10.3762/bxiv.2020.94.v1

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