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An Expeditious Approach to Tetrazoles from Amides Utilizing Phosphorazidates

Kotaro Ishihara, Takayuki Shioiri and Masato Matsugi*

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

K. Ishihara, T. Shioiri, M. Matusugi, Org. Lett., 2020, 22, 6244-6247.

DOI: 10.1021/acs.orglett.0c01890



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Abstract

In a synthesis of tetrazoles from amides, diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate act as both the activator of amide-oxygen for elimination and azide source. Various amides were converted into 1,5-disubstituted and 5-substituted 1H-tetrazoles in good yields without the use of toxic or explosive reagents.

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Key Words

tetrazoles


ID: J54-Y2020