Issue 9, 2022

Alkali-amide controlled selective synthesis of 7-azaindole and 7-azaindoline through domino reactions of 2-fluoro-3-methylpyridine and aldehydes

Abstract

Azaindoles and azaindolines are important core structures in pharmaceuticals and natural products, which have found wide applications in the field of medicinal chemistry. In this study, we developed a novel one-pot method for selectively synthesizing 7-azaindoles and 7-azaindolines, which can be generated by reactions between the readily available 2-fluoro-3-methylpyridine and arylaldehydes. The chemoselectivity is counterion dependent, with LiN(SiMe3)2 generating 7-azaindolines and KN(SiMe3)2 furnishing 7-azaindoles. A range of substituents can be introduced under these conditions, providing handles for further elaboration and functionalization.

Graphical abstract: Alkali-amide controlled selective synthesis of 7-azaindole and 7-azaindoline through domino reactions of 2-fluoro-3-methylpyridine and aldehydes

Supplementary files

Article information

Article type
Research Article
Submitted
01 Mar 2022
Accepted
19 Mar 2022
First published
24 Mar 2022

Org. Chem. Front., 2022,9, 2541-2548

Author version available

Alkali-amide controlled selective synthesis of 7-azaindole and 7-azaindoline through domino reactions of 2-fluoro-3-methylpyridine and aldehydes

X. Xu, M. Ou, Y. Wang, T. Lin, D. Xiong, F. Xue, P. J. Walsh and J. Mao, Org. Chem. Front., 2022, 9, 2541 DOI: 10.1039/D2QO00339B

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