4.8 Article

An Expeditious Approach to Tetrazoles from Amides Utilizing Phosphorazidates

Journal

ORGANIC LETTERS
Volume 22, Issue 16, Pages 6244-6247

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01890

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Funding

  1. JSPS KAKENHI [JP19K07006]
  2. Takahashi Industrial and Economic Research Foundation (public interest incorporated foundation) [10-003-181]

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A novel method was developed for the synthesis of tetrazoles from amides utilizing diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate as both the activator of amide-oxygen for elimination and azide source. Various amides were converted into the corresponding tetrazoles in good yields. This synthetic method allows to prepare 1,5-disubstituted and 5-substituted 1H-tetrazoles from various amides without the use of toxic or explosive reagents.

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