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Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 5: 1006 - 1009

DOI: https://doi.org/10.6023/cjoc201311036

Notes

A Facile and Efficient Synthesis of 2-Amino-1,3-dicarbonitrile-4-aryl-5,6,7,8,9,10,11,12,13,14-decahydrobenzo[12]annulene Derivatives

  • Xie Ruilun ,
  • Zong Zhimin ,
  • Wei Xianyong ,
  • Gao Yanian ,
  • Cheng Ming ,
  • Rong Liangce
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  • a School of Chemical Engineering and Technology, China University of Mining and Technology, Xuzhou 221008;
    b College of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116

Received date: 2013-11-21

  Revised date: 2014-01-10

  Online published: 2014-01-22

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 20936007, 51134021, 51074153, 21276268), the National Basic Research Program of China (Nos. 2011CB201302, 2012CB215302).

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Abstract

A facile and efficient synthesis of 2-amino-1,3-dicarbonitrile-4-aryl-5,6,7,8,9,10,11,12,13,14-decahydrobenzo[12]-annulene derivatives by the reaction of aromatic aldehydes, cyclododecanone, and malononitrile in the presence of benzylamine in 95% EtOH is reported. Benzyamine as base to catalyze this kind of reaction has not been reported. This protocol has the advantages of short reaction time, mild conditions, and easy work-up. The products were identified by IR, 1H NMR and HRMS. The reported method is the efficient approach for the synthesis of these compounds.

Key words： annulene; cyclododecanone; malononitrile; multicomponent reactions

Cite this article

Xie Ruilun , Zong Zhimin , Wei Xianyong , Gao Yanian , Cheng Ming , Rong Liangce . A Facile and Efficient Synthesis of 2-Amino-1,3-dicarbonitrile-4-aryl-5,6,7,8,9,10,11,12,13,14-decahydrobenzo[12]annulene Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(5) : 1006 -1009 . DOI: 10.6023/cjoc201311036

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