Categories: Synthesis of N-Heterocycles > benzo-fused N-Heterocycles >
Synthesis of tetrazolo[1,5-a]pyridines
Recent Literature
The reaction of 2-halopyridines with trimethylsilyl azide in the presence of
tetrabutylammonium fluoride hydrate gives tetrazolo[1,5-a]pyridines.
8-bromotetrazolo[1,5-a]pyridine is further transformed into a variety of
novel tetrazolo[1,5-a]pyridine derivatives.
J. K. Laha, G. D. Cuny, Synthesis, 2008,
4002-4006.
Treatment of pyridine N-oxides with 4-toluene sulfonyl chloride and
sodium azide in toluene at elevated temperature enables an efficient and
convenient synthesis of tetrazolopyridines.
S. Liu, D. Lentz, C. C. Tzschucke, J. Org. Chem., 2014,
79, 3249-3254.
Pyridine N-oxides were converted to tetrazolo[1,5-a]pyridines in good yield in the presence of sulfonyl or phosphoryl azides and pyridine by
heating in the absence of solvent. Diphenyl phosphorazidate (DPPA) was the
most convenient reagent.
J. M. Keith, J. Org. Chem., 2006,
71, 9540-9543.