Synthesis of fluorinated isoxazoles using Selectfluorℿ preparation and characterization of 4-fluoroisoxazole, 4,4,5-trifluoroisoxazoline and 4,4-difluoro-5-hydroxyisoxazoline systems from one-pot and multi-step processes

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• 作者：Kazuyuki Sato^a ; ^b ; ^{sato@pharm.setsunan.ac.jp" class="auth_mail" title="E-mail the corresponding author} ; Graham Sandford^a ; ^{graham.sandford@durham.ac.uk" class="auth_mail" title="E-mail the corresponding author} ; Keiji Shimizu^b ; Satomi Akiyama^b ; Marcus J. Lancashire^a ; Dmitry S. Yufit^a ; Atsushi Tarui^b ; Masaaki Omote^b ; Itsumaro Kumadaki^b ; Shinya Harusawa^c ; Akira Ando^b
• 关键词：Fluoroheteroaromatic ; Selective fluorination ; 4-Fluoroisoxazole ; 4 ; 4 ; 5-Trifluoroisoxazoline TRPV1 antagonist
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：31 March 2016
• 年：2016
• 卷：72
• 期：13
• 页码：1690-1698
• 全文大小：1198 K

文摘

3,5-Disubstituted 4-fluoroisoxazole, 4,4,5-trifluoroisoxazoline and 4,4-difluoro-5-hydroxyisoxazoline products were obtained from reaction of the corresponding isoxazoles with Selectfluor™ depending upon the reaction conditions. Although the fluorinations proceeded using conventional heating, microwave (μW) irradiation considerably shortened reaction times and enabled a high yielding one-pot cascade fluorination-cyclization from simple diketone substrates. In addition, a related 4-fluoroisoxazole-3-carboxyamide derivative was synthesized.