Citation: Tang Zilong, Wang Ming, Yao Yuan, Tan Jingzhao, Dai Ningning, Li Xinxing, Peng Lifen, Jiao Yinchun. Chemoselective Synthesis of Substituted Benzoxazines and Imidazolidines by Reactions of Hydroxyl Substituted Ethylenediamine Derivatives with Aldehydes[J]. Chinese Journal of Organic Chemistry, ;2019, 39(3): 800-810. doi: 10.6023/cjoc201808003 shu

Chemoselective Synthesis of Substituted Benzoxazines and Imidazolidines by Reactions of Hydroxyl Substituted Ethylenediamine Derivatives with Aldehydes

Tang Zilong ^a,b,, ,
Wang Ming ^a,b ,
Yao Yuan ^a,b ,
Tan Jingzhao ^a,b ,
Dai Ningning ^a,b ,
Li Xinxing ^a,b ,
Peng Lifen ^a ,
Jiao Yinchun ^b

a.
Key Laboratory of Theoretical Organic Chemistry and Functional Molecular, Ministry of Education, Hunan University of Science and Technology, Xiangtan 411201
b.
Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201

Corresponding author: Tang Zilong, zltang67@aliyun.com
Received Date: 6 August 2018
Revised Date: 10 September 2018
Available Online: 26 March 2018
Fund Project: the National Natural Science Foundation of China 21372070the Scientific Research Fund of Hunan Provincial Education Department 17A066the National Natural Science Foundation of China 21877034Project supported by the National Natural Science Foundation of China (Nos. 21877034, 21372070) and the Scientific Research Fund of Hunan Provincial Education Department (No. 17A066)

Figures(4)

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.
- hydroxyl substituted ethylenediamine,
- 1, 3-imidazolidine,
- 3, 1-benzoxazine,
- chemoselectivity,
- synthesis
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