A Fast and Efficient Approach for Screening and Synthesis of the Products of 2-Pyrimidinyloxy-N-arylbenzylamine Derivatives via Acid-Catalyzed Smiles Rearrangement

doi:10.6023/cjoc201604020

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (12): 2997-3002.DOI: 10.6023/cjoc201604020 Previous Articles Next Articles

NOTE

2-嘧啶氧基-N-芳基苄胺类衍生物的酸催化Smiles重排反应条件的快速筛选和产物的高效制备

叶美君^a, 张培志^b, 吴军^c

a 中华全国供销合作总社杭州茶叶研究院杭州 310016;
b 浙江科技学院生物与化学工程学院杭州 310023;
c 浙江大学化学系杭州 310027

收稿日期:2016-04-10 修回日期:2016-06-02 发布日期:2016-08-10
通讯作者: 叶美君, 吴军 E-mail:yemjmj@163.com;wujunwu@zju.edu.cn
基金资助:
公益性行业（农业）科研专项（No. 201403030）和国家自然科学基金（No. 31471807）资助项目.

A Fast and Efficient Approach for Screening and Synthesis of the Products of 2-Pyrimidinyloxy-N-arylbenzylamine Derivatives via Acid-Catalyzed Smiles Rearrangement

Ye Meijun^a, Zhang Peizhi^b, Wu Jun^c

a Hangzhou Tea Research Institute, All China Federation of Supply and Marketing Cooperatives, Hangzhou 310016;
b School of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310023;
c Department of Chemistry, Zhejiang University, Hangzhou 310027

Received:2016-04-10 Revised:2016-06-02 Published:2016-08-10
Supported by:
Project supported by the Agro-scientific Research in the Public Interest (No. 201403030) and the National Natural Science Foundation of China (No. 31471807).

1. A Fast and Efficient Approach for Screening and Synthesis of the Products of 2-Pyrimidinyloxy-N-arylbenzylamine Derivatives via Acid-Catalyzed Smiles Rearrangement.PDF(362KB)

Abstract

Based on high performance liquid chromatography (HPLC), a fast, efficient and simple route for Smiles rearrangement reaction has been developed in the presence of 2-pyrimidinyloxy-N-arylbenzylamine derivatives as reactants with HCl as acid catalyst in mixed CH₃OH/H₂O medium at room temperature. The advantage of the proposed method is that the products with excellent yields and high purity can be obtained employing reused solvent without further separating process. Considering the cheapness of catalyst and solvent, as well as high efficient and environment-friendly reaction condition, the developed method has the practicability and environmentally friendliness.

Key words: 2-pyrimidinyloxy-N-arylbenzylamine derivatives, Smiles rearrangement, acid-catalyzed reaction, substituent effect, HPLC

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Ye Meijun, Zhang Peizhi, Wu Jun. A Fast and Efficient Approach for Screening and Synthesis of the Products of 2-Pyrimidinyloxy-N-arylbenzylamine Derivatives via Acid-Catalyzed Smiles Rearrangement[J]. Chin. J. Org. Chem., 2016, 36(12): 2997-3002.

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2-嘧啶氧基-N-芳基苄胺类衍生物的酸催化Smiles重排反应条件的快速筛选和产物的高效制备

A Fast and Efficient Approach for Screening and Synthesis of the Products of 2-Pyrimidinyloxy-N-arylbenzylamine Derivatives via Acid-Catalyzed Smiles Rearrangement

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