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

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

DOI: 10.1055/a-1800-2011


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Abstract

The reaction of various nitrones with bis(p-nitrophenyl) phosphorazidate provides 1,5-disubstituted tetrazoles in the presence of 4-(dimethylamino)pyridine without the need for toxic or explosive reagents.

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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.

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

nitrones, bisnitrophenyl phosphorazidate, azides, tetrazoles, cycloaddition


ID: J72-Y2022