Oleylamine-catalyzed Tandem Knoevenagel/Michael Addition of 1,3-Cyclohexanediones with Aromatic Aldehydes

doi:10.1007/s40242-018-7320-1

Chemical Research in Chinese Universities ›› 2018, Vol. 34 ›› Issue (2): 186-190.doi: 10.1007/s40242-018-7320-1

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Oleylamine-catalyzed Tandem Knoevenagel/Michael Addition of 1,3-Cyclohexanediones with Aromatic Aldehydes

HE Xinwei¹, WU Yuhao¹, FAN Chenli^1,2, LU Peng¹, ZUO Youpeng¹, SHANG Yongjia¹

1. Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-based Materials(State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. China;
2. Department of Material Engineering, Wuhu Institute of Technology, Wuhu 241003, P. R. China

Received:2017-10-09 Revised:2017-11-22 Online:2018-04-01 Published:2017-12-18
Contact: HE Xinwei,E-mail:xinweihe@mail.ahnu.edu.cn;SHANG Yongjia,E-mail:shyj@mail.ahnu.edu.cn E-mail:xinweihe@mail.ahnu.edu.cn;shyj@mail.ahnu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.21772001, 21372008), the Natural Science Foundation of Education Administration of Anhui Province, China(No.KJ2016A267), the Special and Excellent Research Fund of Anhui Normal Universit and the Doctoral Scientific Research Foundation of Anhui Normal University, China(No.2016XJJ110).

Abstract

Abstract: A convenient and efficient method was developed for the synthesis of 2,2'-(arylmethylene)bis(3-hydrox-ycyclohex-2-enone) derivatives via the oleylamine-catalyzed tandem Knoevenagel/Michael addition reactions of aromatic aldehydes and cyclohexane-1,3-diones. This transformation proceeded without any metal catalyst in non-toxic solvent at room temperature with high isolated yields. A plausible mechanism for this process was proposed.

Key words: 2,2'-(Arylmethylene)bis(3-hydroxycyclohex-2-enone), Knoevenagel condensation, Michael addition, Oleylamine, Tandem reaction

HE Xinwei, WU Yuhao, FAN Chenli, LU Peng, ZUO Youpeng, SHANG Yongjia. Oleylamine-catalyzed Tandem Knoevenagel/Michael Addition of 1,3-Cyclohexanediones with Aromatic Aldehydes[J]. Chemical Research in Chinese Universities, 2018, 34(2): 186-190.

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Oleylamine-catalyzed Tandem Knoevenagel/Michael Addition of 1,3-Cyclohexanediones with Aromatic Aldehydes

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