Tetrazoles rearrangement

The azido/tetrazole rearrangement of pyrazole and indazole derivatives will be discussed in the corresponding section (4.04.2.3.4(v)). 

The Huisgen tetrazole rearrangement is the transformation of C-substituted tetrazole 1 to the corresponding 2,4-disubstituted 1,3,4-oxadiazole 2 by the reaction of carboxylic acid chloride in the presence of a base such as pyridine,... 

Professor Rolf Huisgen discovered the titled reaction in 1958 at the University of Munich. " Huigen s great intuition drove him to ask his Ph.D. student Jurgen Sauer to repeat failed reactions of 5-phenyltetrazole with aroyl chlorides in pyridine that has been run by an an inept postdoctoral fellow, and hence led to the discovery of the named reaction. Since its discovery, the Huisgen tetrazole rearrangement reaction has been used for the synthesis of... 

Scheme 22 The Acyl-Tetrazole Rearrangement Route in the synthesis of fluorinated 1,3,4-oxadiazoles 65, 5-perfluoroalkyl-2-phenyl-l,3,4-oxadiazoles 76 and 1,3-bis(2-phenyl-1,3,4-oxadiazol-5- yl)hexafluoropropane 78...

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