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

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

研究简报

方便、有效的方法合成2-氨基-1,3-二氰基-4-芳基-5,6,7,8,9,10,11,12,13,14-十氢苯并[12]轮烯衍生物

  • 谢瑞伦 ,
  • 宗志敏 ,
  • 魏贤勇 ,
  • 高亚年 ,
  • 陈明 ,
  • 荣良策
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  • a 中国矿业大学化工学院 徐州 221008;
    b 江苏师范大学化学化工学院 徐州 221116

收稿日期: 2013-11-21

  修回日期: 2014-01-10

  网络出版日期: 2014-01-22

基金资助

国家自然科学基金（No. 20936007，51134021，51074153，21276268）和国家基础研究计划（Nos. 2011CB201302，2012CB215302）资助项目.

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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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摘要

芳香醛、环十二酮和丙二腈在苄胺存在下于95%乙醇中反应，方便地合成了一系列2-氨基-1，3-二氰基-4-芳基-5，6，7，8，9，10，11，12，13，14-十氢苯并[12]轮烯衍生物，苄胺作为碱催化此类的反应还未见报道. 产物的结构经过红外、核磁和高分辨质谱确定. 本方法具有反应时间短、容易操作、产率高等优点，是合成此类化合物的一条有效途径.

关键词： 轮烯; 环十二酮; 丙二腈; 多组分反应

本文引用格式

谢瑞伦 , 宗志敏 , 魏贤勇 , 高亚年 , 陈明 , 荣良策 . 方便、有效的方法合成2-氨基-1,3-二氰基-4-芳基-5,6,7,8,9,10,11,12,13,14-十氢苯并[12]轮烯衍生物[J]. 有机化学, 2014 , 34(5) : 1006 -1009 . DOI: 10.6023/cjoc201311036

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

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