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One-Step Conversion of Pyridine N-Oxides to Tetrazolo[1,5-a]pyridines

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John M. Keith

Johnson & Johnson Pharmaceutical Research & Development, L.L.C. 3210 Merryfield Row, San Diego, California 92121 jkeith@prdus.jnj.com

J. Org. Chem., 2006, 71 (25), pp 9540–9543

DOI: 10.1021/jo061819j

Publication Date (Web): November 14, 2006

Abstract

Pyridine N-oxides were converted to tetrazolo[1,5-a]pyridines in good to excellent yield by heating in the presence sulfonyl or phosphoryl azides and pyridine in the absence of solvent. Various sulfonyl and phosphoryl azides were screened for reactivity under a standard set of conditions. Diphenyl phosphorazidate was the most convenient reagent and gave high yields. Reaction optimization, scope, and scalability are discussed.

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Published In Issue December 08, 2006
Received September 1, 2006

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One-Step Conversion of Pyridine N-Oxides to Tetrazolo[1,5-a]pyridines

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

A General and Efficient 2-Amination of Pyridines and Quinolines

One Step Conversion of Heteroaromatic-N-Oxides to Imidazolo-Heteroarenes

Deprotonative Magnesation and Cadmation of [1,2,3]Triazolo[1,5-a]pyridines

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