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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
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)
2009
发表期刊Tetrahedron
ISSN0040-4020
卷号65期号:21页码:4212-4219
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.
学科领域有机氟化学
部门归属上海有机所; 上海大学
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收录类别SCI
语种英语
WOS记录号WOS:000266055300017
引用统计
被引频次:26[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/14466
专题中科院有机氟化学重点实验室
通讯作者Zhu SZ(朱仕正); Hao J(郝健)
推荐引用方式
GB/T 7714
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.
APA 万文.,侯杰.,蒋海珍.,王艳丽.,朱仕正.,...&郝健.(2009).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.Tetrahedron,65(21),4212-4219.
MLA 万文,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".Tetrahedron 65.21(2009):4212-4219.
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