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学科主题: 有机氟化学
题名: Concise synthesis of omega-fluoroalkylated ketoesters. A building block for the synthesis of six-, seven-, and eight-membered fluoroalkyl substituted 1,2-diaza-3-one heterocycles
其他题名: 氟烷基酮类的简便合成--一种合成6,7,8员包含1,2-二唑-3-酮杂环化合物的切块
作者: Wan W(万文) ; Hou J(侯杰) ; Jiang HZ(蒋海珍) ; Wang YL(王艳丽) ; Zhu SZ(朱仕正) ; Deng HM(邓红梅) ; Hao J(郝健)
通讯作者: 朱仕正 ; 郝健
刊名: Tetrahedron
发表日期: 2009
卷: 65, 期:21, 页:4212-4219
收录类别: SCI
部门归属: 上海有机所; 上海大学
英文摘要: A concise and general synthetic route toward the small and medium-sized fluoroalkyl substituted 1.2-diaza-3-one heterocyclic ring skeletons via a sequential reaction of condensation and ring-closure reaction of omega-fluoroalkylated ketoesters 4 with hydrazines 5 catalyzed by 10-20 mol % TsOH has been developed. A practical preparation of biologically interested omega-fluoroalkylated ketoesters 4, which were subsequently Subjected as a fluorine-containing building block to the synthesis of 1,2-diaza-3-one heterocycles has been optimized. Trifluoromethyl substituted seven- and eight-membered 1,2-diazapinone 8, 1,2-diazocinone 10 were also obtained via this sequential reaction of delta- (or epsilon-) trifluoromethyl ketoesters with hydrazine hydrates in acidic condition. In contrast, the sequential reaction of omega-fluoroalkylated delta- or epsilon-ketoesters with aryl hydrazines under the same conditions did not result in the formation of diazepinones and diazocinones, and instead, the reaction provided a direct access to the biologically important 2-fluoroalkyl-indole-3-carboxylate derivatives via a Fisher indole synthesis. (C) 2009 Elsevier Ltd. All rights reserved.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000266055300017
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/14466
Appears in Collections:中科院有机氟化学重点实验室_期刊论文

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Recommended Citation:
Wan W,Hou J,Jiang HZ,et al. Concise synthesis of omega-fluoroalkylated ketoesters. A building block for the synthesis of six-, seven-, and eight-membered fluoroalkyl substituted 1,2-diaza-3-one heterocycles[J]. Tetrahedron,2009,65(21):4212-4219.
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