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

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

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

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

DOI: 10.1055/s-0036-1591851

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Abstract

5-Substituted 1H-tetrazoles were effectively synthesized in short reaction times from aldoximes and diphenyl phosphorazidate (DPPA) under reflux conditions in xylenes. Various aldoximes underwent the cycloaddition reaction to afford the corresponding 5-substituted 1H-tetrazoles in good yields. Chiral aldoximes gave aminotetrazoles with almost no racemization.

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

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

Synthesis of 1,5-Disubstituted Tetrazoles from Nitrones by Using Bis(p-nitrophenyl) Phosphorazidate in the Presence of 4-(Dimethylamino)pyridine

K. Ishihara, T. Shioiri, M. Matsugi, Synlett, 2022, 33, 781-784.

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Key Words

aldoximes, tetrazoles, diphenyl phosphorazidate, azides, cycloaddition

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ID: J66-Y2018