A facile one-pot synthesis of 2-fluoroalkyl 1,3-imidazolines and 1,3-oxazolines through imidoyl halide intermediates

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	A facile one-pot synthesis of 2-fluoroalkyl 1,3-imidazolines and 1,3-oxazolines through imidoyl halide intermediates
	Jiang HZ(蒋海珍) ; Sun L(孙兰) ; Yuan SJ(袁世杰) ; Lu WJ(卢文君) ; Wan W(万文) ; Zhu SZ(朱仕正) ; Hao J(郝建)
刊名	Tetrahedron
	2012
卷号	68 期号:13 页码:2858-2863
ISSN号	0040-4020
其他题名	亚胺酰卤中间体参与下的一锅法合成2-氟烷基1,3-咪唑啉或1,3-恶唑啉
通讯作者	蒋海珍 ; 朱仕正 ; 郝建
英文摘要	A facile one-pot procedure has been developed for the synthesis of 1,3-imidazolines and 1,3-oxazolines bearing fluorinated alkyl groups at the 2-position. The reaction involves the condensation of N-monosubstituted ethane-1,2-diamines or 2-aminoethanols with a fluorinated carboxylic acid in the presence of PPh3/CX4. The proposed mechanism is that the amide intermediates were initially formed, and then converted to the imidoyl halide intermediates in the presence of PPh3/CX4, followed by rapid intramolecular cyclization to 1,3-diazoline products. This protocol allows for the synthesis of 2-bromodifluoromethyl-1,3-imidazoline, a useful CF2Br-heterocyclic building block, which can be used for the synthesis of gem-difluoromethylene linked compounds. (C) 2012 Elsevier Ltd. All rights reserved.
学科主题	氟化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1016/j.tet.2012.01.086
语种	英语
WOS记录号	WOS:000301964700014
公开日期	2013-08-23
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/28267]
专题	上海有机化学研究所_中科院有机氟化学重点实验室
推荐引用方式 GB/T 7714	Jiang HZ,Sun L,Yuan SJ,et al. A facile one-pot synthesis of 2-fluoroalkyl 1,3-imidazolines and 1,3-oxazolines through imidoyl halide intermediates[J]. Tetrahedron,2012,68(13):2858-2863.
APA	蒋海珍.,孙兰.,袁世杰.,卢文君.,万文.,...&郝建.(2012).A facile one-pot synthesis of 2-fluoroalkyl 1,3-imidazolines and 1,3-oxazolines through imidoyl halide intermediates.Tetrahedron,68(13),2858-2863.
MLA	蒋海珍,et al."A facile one-pot synthesis of 2-fluoroalkyl 1,3-imidazolines and 1,3-oxazolines through imidoyl halide intermediates".Tetrahedron 68.13(2012):2858-2863.