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Synthesis of 5-Substituted 1H-Tetrazoles from Aldoximes Using Diphenyl Phosphorazidate

Kotaro Ishihara, Mayumi Kawashima, Takayuki Shioiri, Masato Matsugi*

*Department of Applied Biological Chemistry, Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tempaku-ku, Nagoya 468-8502, Japan, Email: matsugimeijo-u.ac.jp

K. Ishihara, M. Kawashima, T. Shioiri, M. Matsugi, Synlett, 2016, 27, 2225-2228.

DOI: 10.1055/s-0035-1561668 (free Supporting Information)


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Abstract

Aromatic and aliphatic aldoximes underwent a cycloaddition with diphenyl phosphorazidate (DPPA) to afford the corresponding 5-substituted 1H-tetrazoles with ease and efficiency.


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A Practical Synthesis of 5-Substituted 1H-Tetrazoles from Aldoximes Employing the Azide Anion from Diphenyl Phosphorazidate

K. Ishihara, M. Kawashima, T. Matsumoto, T. Shiori, M. Matsugi, Synthesis, 2018, 50, 1141-1151.


Key Words

diphenyl phosphorazidate, aldoximes, azides, cycloaddition, tetrazoles


ID: J60-Y2016