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

Kotaro Ishihara; Mayumi Kawashima; Takatoshi Matsumoto; Takayuki Shioiri; Masato Matsugi

doi:10.1055/s-0036-1591851

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

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

Division of Organic- and Biomaterials Research

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

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

Original language	English
Pages (from-to)	1293-1300
Number of pages	8
Journal	Synthesis (Germany)
Volume	50
Issue number	6
DOIs	https://doi.org/10.1055/s-0036-1591851
Publication status	Published - 2018 Mar 15

Keywords

aldoximes
azides
cycloaddition
diphenyl phosphorazidate
tetrazoles

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-0036-1591851

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

abstract = "5-Substituted 1 H -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 1 H -tetrazoles in short reaction times and in good yields. Chiral aldoximes derived from amino acids also gave aminotetrazoles with almost no racemization.",

keywords = "aldoximes, azides, cycloaddition, diphenyl phosphorazidate, tetrazoles",

author = "Kotaro Ishihara and Mayumi Kawashima and Takatoshi Matsumoto and Takayuki Shioiri and Masato Matsugi",

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AU - Ishihara, Kotaro

AU - Kawashima, Mayumi

AU - Matsumoto, Takatoshi

AU - Shioiri, Takayuki

AU - Matsugi, Masato

N1 - Funding Information: This work was supported by JSPS Grant-in-Aid for Scientific Research (C), 26450145, and Prof. Y. Uozumi’s JST-ACCEL program (JPM-JAC1401).SJPS Grann-it-Adi ofr Seccinifit Reseacrh C( 2(6450145SJ)TACCEL PJ(MAJC1401) Publisher Copyright: © Georg Thieme Verlag Stuttgart New York.

PY - 2018/3/15

Y1 - 2018/3/15

N2 - 5-Substituted 1 H -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 1 H -tetrazoles in short reaction times and in good yields. Chiral aldoximes derived from amino acids also gave aminotetrazoles with almost no racemization.

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

KW - aldoximes

KW - azides

KW - cycloaddition

KW - diphenyl phosphorazidate

KW - tetrazoles

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

Abstract

Keywords

ASJC Scopus subject areas

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