Alkali-amide controlled selective synthesis of 7-azaindole and 7-azaindoline through domino reactions of 2-fluoro-3-methylpyridine and aldehydes?
Organic Chemistry Frontiers Pub Date: 2022-03-24 DOI: 10.1039/D2QO00339B
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.
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Journal Name：Organic Chemistry Frontiers
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CAS no.: 89640-58-4
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