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Substituted 1H-1,2,3-Triazol-4-yl-1H-pyrrolo[2,3-b]pyridines by De Novo One-Pot Ring-Forming Coupling/Cyclization/Desilylation Cu Alkyne/Azide Cycloaddition (AAC) Sequence

Substituted 1H-1,2,3-Triazol-4-yl-1H-pyrrolo[2,3-b]pyridines by De Novo One-Pot Ring-Forming Coupling/Cyclization/Desilylation Cu Alkyne/Azide Cycloaddition (AAC) Sequence

Timo Lessing, Hauke van Mark, Thomas J J Müller

Chemistry. 2018 Jun 26;24(36):8974-8979.

PMID: 29726615

Abstract:

Substituted 1H-1,2,3-triazol-4-yl-pyrrolo[2,3-b]pyridines are efficiently prepared by a one-pot coupling/cyclization/desilylation Cu alkyne/azide cycloaddition (CuAAC) sequence in the sense of a consecutive three-component fashion. The key feature of this new de novo formation of azole and triazole anellation is the sequentially Pd/Cu-catalyzed process employing tri(iso-propyl)silyl (TIPS) butadiyne as a four-carbon building block. In addition, the sequence can be expanded in a four-component fashion also employing the in situ formation of the required azides.

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