An Improved Synthesis of 2,5-Disubstituted Tetrazoles
Mikhail Krasavin shows the [3+2] cycloaddition of α-diazocarbonyl compounds with arenediazonium salts.
[3+2]-Cycloaddition of α-Diazocarbonyl Compounds with Arenediazonium Salts Catalyzed by Silver Nitrate Delivers 2,5-Disubstituted Tetrazoles: S. Chuprun, D. Dar’in, G. Kantin, M. Krasavin
Synthesis 2019, DOI: 10.1055/s-0039-1690159
Tetrazoles have a special place in medicinal chemistry, as there are a number of bioactive compounds and drugs (such as Losartan and Valsartan) incorporating this heterocycle, which can also be used as a bioisosteric replacement of the carboxylic and amide functions. Professor Mikhail Krasavin and his group from Saint Petersburg State University (Russian Federation) have recently developed an improved approach to functionalized 2,5-disubstituted tetrazoles, using a silver-catalyzed [3+2] cycloaddition of α-diazocarbonyl derivatives with arenediazonium salts.
Professor Krasavin said: “[3+2] Cycloaddition of arenediazonium salts with diazo compounds is a powerful way of making medicinally important tetrazoles. The range of diazo compounds employable in this transformation had been rather limited. We extended it to include α-diazocarbonyl compounds, the most widespread type of reagents.”