Synthesis 2012; 44(20): 3158-3160
DOI: 10.1055/s-0032-1317147
short paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2,4,6-Triazidopyridine and Its 3,5-Diiodo Derivative

Sergei V. Chapyshev*
Institute of Problems of Chemical Physics, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russian Federation, Fax: +7(496)5223507   Email: chap@icp.ac.ru
,
Alexander V. Chernyak
Institute of Problems of Chemical Physics, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russian Federation, Fax: +7(496)5223507   Email: chap@icp.ac.ru
› Author Affiliations
Further Information

Publication History

Received: 25 June 2012

Accepted after revision: 27 July 2012

Publication Date:
16 August 2012 (online)


Abstract

2,4,6-Trifluoropyridine was diiodinated with a mixture of potassium iodide and periodic acid in sulfuric acid at 55 °C to give 2,4,6-trifluoro-3,5-diiodopyridine in 85% yield. Both the starting trifluoropyridine and its 3,5-diiodo derivative readily react with excess sodium azide in dimethyl sulfoxide at room temperature to afford 2,4,6-triazidopyridine and 2,4,6-triazido-3,5-diiodopyridine in high yields. In the 15N NMR spectra of the triazides, the Nα atoms of the α- and γ-azido groups show very differing chemical shifts, which indicates the different reactivity of these groups in 1,3-dipolar cycloaddition, phosphorylation, reduction, thermolysis, and photolysis reactions.

 
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