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Synthesis 2018; 50(06): 1293-1300
DOI: 10.1055/s-0036-1591851
paper
© Georg Thieme Verlag Stuttgart · New York

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

Kotaro Ishihara
a   Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tempaku, Nagoya 468-8502, Japan   Email: matsugi@meijo-u.ac.jp
,
Mayumi Kawashima
a   Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tempaku, Nagoya 468-8502, Japan   Email: matsugi@meijo-u.ac.jp
,
Takatoshi Matsumoto
b   Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1, Katahira, Aobaku, Sendai 980-8577, Japan
,
Takayuki Shioiri
a   Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tempaku, Nagoya 468-8502, Japan   Email: matsugi@meijo-u.ac.jp
,
Masato Matsugi*
a   Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tempaku, Nagoya 468-8502, Japan   Email: matsugi@meijo-u.ac.jp
› Author AffiliationsThis work was supported by JSPS Grant-in-Aid for Scientific Research (C), 26450145, and Prof. Y. Uozumi’s JST-ACCEL program (JPMJAC1401).
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Publication History

Received: 13 September 2017

Accepted after revision: 07 November 2017

Publication Date:
12 December 2017 (online)

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Abstract

5-Substituted 1H-tetrazoles were effectively synthesized 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 short reaction times and in good yields. Chiral aldoximes derived from amino acids also gave aminotetrazoles with almost no racemization.

Keywords

diphenyl phosphorazidate - aldoximes - azides - cycloaddition - tetrazoles

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    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591851.
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