羟基取代乙二胺衍生物与醛反应化学选择性合成取代苯并噁嗪和咪唑啉
收稿日期: 2018-08-06
修回日期: 2018-09-10
网络出版日期: 2018-10-26
基金资助
国家自然科学基金（Nos.21877034，21372070）和湖南省教育厅科学研究基金（No.17A066）.
Chemoselective Synthesis of Substituted Benzoxazines and Imidazolidines by Reactions of Hydroxyl Substituted Ethylenediamine Derivatives with Aldehydes
Received date: 2018-08-06
Revised date: 2018-09-10
Online published: 2018-10-26
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21877034, 21372070) and the Scientific Research Fund of Hunan Provincial Education Department (No. 17A066).
唐子龙 , 汪明 , 姚园 , 谭经照 , 代宁宁 , 李新兴 , 彭丽芬 , 焦银春 . 羟基取代乙二胺衍生物与醛反应化学选择性合成取代苯并噁嗪和咪唑啉[J]. 有机化学, 2019 , 39(3) : 800 -810 . DOI: 10.6023/cjoc201808003
Lewis acid La(OTf) 3-catalyzed chemoselective cyclization of hydroxyl substituted ethylenediamine derivatives with aldehydes has been described for the first time, which provides efficient access to diversely functionalized 1,3-imidazoli-dines and 3,1-benzoxazines in generally good yields only by adjusting the position of the methylene group within hydroxyl substituted ethylenediamines. The reaction is suitable to aromatic aldehydes and aliphatic ones. Plausible mechanisms are also proposed to explain the observed reaction modes, wherein the nucleophilicity of nitrogen and oxygen atoms plays an important role in controlling the chemoselectivity.
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