Synthesis, Inhaltsverzeichnis Synthesis 2018; 50(06): 1293-1300DOI: 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 › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik 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 Keywordsdiphenyl phosphorazidate - aldoximes - azides - cycloaddition - tetrazoles Volltext Referenzen References 1 Butler RN. In Comprehensive Heterocyclic Chemistry . Vol. 4. Katritzky AR. Rees CW. Scriven EF. V. Pergamon; Oxford: 1996: 674 2a Herr RJ. Bioorg. Med. Chem. 2002; 10: 3379 2b McKie HA. Friedland S. Hof F. Org. Lett. 2008; 10: 4653 3a Chiu AT. Dunica JV. McCall DE. Wong PC. Price WA. Thoolen MJ. Carini DJ. Johnson AL. Timmermans PB. J. Pharmacol. Exp. Ther. 1989; 250: 867 3b Buehlmayer P. Criscione L. Fuhrer W. Furet P. De Gasparo M. Stutz S. Whitebread S. J. Med. Chem. 1991; 34: 3105 3c Kinugawa K. Kohmoto O. Takahashi T. Serizawa T. Eur. J. Pharmacol. 1993; 235: 313 3d Shibouta Y. Inada Y. Ojima M. Wada T. 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