Regioselective Preparation of Enaminone via Enol Methyl Ether of 3-Acetyl-2-butenolide and Different Amines

doi:10.6023/cjoc201611013

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (4): 975-986.DOI: 10.6023/cjoc201611013 Previous Articles Next Articles

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经由3-乙酰基-2-丁烯内酯烯醇醚与胺类衍生物区域选择性制备烯胺酮

赵宇, 汤博, 刘鑫磊, 李婉祯, 黄铭一, 王明安

中国农业大学应用化学系北京 100193

收稿日期:2016-11-10 修回日期:2016-12-14 发布日期:2016-12-21
通讯作者: 王明安 E-mail:wangma@cau.edu.cn
基金资助:
国家自然科学基金（No.21172254）和国家十二五科技支撑计划（No.2011BAE06B04）资助项目.

Regioselective Preparation of Enaminone via Enol Methyl Ether of 3-Acetyl-2-butenolide and Different Amines

Zhao Yu, Tang Bo, Liu Xinlei, Li Wanzhen, Huang Mingyi, Wang Ming'an

Department of Applied Chemistry, China Agricultural University, Beijing 100193

Received:2016-11-10 Revised:2016-12-14 Published:2016-12-21
Contact: 10.6023/cjoc201611013 E-mail:wangma@cau.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21172254) and the National Key Technologies R&D Program of China (No. 2011BAE06B04).

1. Regioselective Preparation of Enaminone via Enol Methyl Ether of 3-Acetyl-2-butenolide and Different Amines.PDF(3326KB)

Abstract

The regioselective addition-elimination of 3-acetyl-4-methoxy-2-butenolide and 3-(1-methoxy ethylidene)furan- 2,4-dione having enol ether with different amines yielded novel stable enaminone derivatives in ethanol solution. Their structures were elucidated by ¹H NMR, ¹³C NMR, HRMS and X-ray diffraction data. Among of them, the Z/E isomers were observed for 3-(1-aminoethylidene)-furan-2,4-dione. The structures of byproducts for preparing intermediates and title compounds were also characterized.

Key words: 3-acetyl-4-methoxy-2-butenolide, 3-(1-methoxyethylidene)-furan-2,4-dione, addition-elimination, enaminone

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Zhao Yu, Tang Bo, Liu Xinlei, Li Wanzhen, Huang Mingyi, Wang Ming'an. Regioselective Preparation of Enaminone via Enol Methyl Ether of 3-Acetyl-2-butenolide and Different Amines[J]. Chin. J. Org. Chem., 2017, 37(4): 975-986.

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经由3-乙酰基-2-丁烯内酯烯醇醚与胺类衍生物区域选择性制备烯胺酮

Regioselective Preparation of Enaminone via Enol Methyl Ether of 3-Acetyl-2-butenolide and Different Amines

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