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This content will become publicly available on May 3, 2023

Title: Alkali-amide controlled selective synthesis of 7-azaindole and 7-azaindoline through domino reactions of 2-fluoro-3-methylpyridine and aldehydes
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(SiMe 3 ) 2 generating 7-azaindolines and KN(SiMe 3 ) 2 furnishing 7-azaindoles. A range of substituents can be introduced under these conditions, providing handles for further elaboration and functionalization.
Authors:
; ; ; ; ; ; ;
Award ID(s):
1902509
Publication Date:
NSF-PAR ID:
10348019
Journal Name:
Organic Chemistry Frontiers
Volume:
9
Issue:
9
Page Range or eLocation-ID:
2541 to 2548
ISSN:
2052-4129
Sponsoring Org:
National Science Foundation
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