Palladium-Catalyzed Chemoselective Monoarylation of Hydrazides for the Synthesis of [1,2,4]Triazolo[4,3-a]pyridines

Palladium-Catalyzed Chemoselective Monoarylation of Hydrazides for the Synthesis of [1,2,4]Triazolo[4,3-a]pyridines

An efficient and convenient method for the synthesis of [1,2,4]triazolo[4,3-a]pyridines was exemplified by the synthesis of 20 analogues bearing a variety of substituents at the 3-position. The methodology involves a palladium-catalyzed addition of hydrazides to 2-chloropyridine, which occurs chemos...

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Bibliographic Details
Published in:Organic letters Vol. 12; no. 4; pp. 792 - 795
Main Authors: Reichelt, Andreas, Falsey, James R, Rzasa, Robert M, Thiel, Oliver R, Achmatowicz, Michal M, Larsen, Robert D, Zhang, Dawei
Format: Journal Article
Language:English
Published: United States American Chemical Society 19-02-2010
Subjects:
Acetic Acid - chemistry
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Hydrazines - chemistry
Microwaves
Molecular Structure
Palladium - chemistry
Pyridines - chemical synthesis
Pyridines - chemistry
Triazoles - chemical synthesis
Triazoles - chemistry
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Summary:An efficient and convenient method for the synthesis of [1,2,4]triazolo[4,3-a]pyridines was exemplified by the synthesis of 20 analogues bearing a variety of substituents at the 3-position. The methodology involves a palladium-catalyzed addition of hydrazides to 2-chloropyridine, which occurs chemoselectively at the terminal nitrogen atom of the hydrazide, followed by dehydration in acetic acid under microwave irradiation.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol902868q