有机化学 ›› 2014, Vol. 34 ›› Issue (9): 1889-1894.DOI: 10.6023/cjoc201403051 上一篇    下一篇

研究简报

5-芳基四氮唑衍生物的高效合成方法与酯基的伴生降解

孙宏滨a, 孙源华a, 陈文龙b, 秦鹏a, 齐轩a   

  1. a 东北大学理学院, 沈阳 110819;
    b 攀钢集团研究院有限公司, 钒钛资源综合利用国家重点实验室, 攀枝花 617000
  • 收稿日期:2014-03-25 修回日期:2014-04-25 出版日期:2014-09-25 发布日期:2014-05-07
  • 通讯作者: 孙宏滨, 齐轩 E-mail:sunhb@mail.neu.edu.cn
  • 基金资助:

    国家自然科学基金(No. 21003018)资助项目.

An Efficient Approach to the Synthesis of 5-Aryl-1H-tetrazole Derivatives Accompanying with the Cleavage of Ester Group

Sun Hongbina, Sun Yuanhuaa, Chen Wenlongb, Qin Penga, Qi Xuana   

  1. a Department of Chemistry, Northeastern University, Shenyang 110819;
    b Pangang Group ResearchInstitude Co., Ltd., State Key Laboratory of Vanadium and Titanium Resources Comprehensive Utilization, Panzhihua 617000
  • Received:2014-03-25 Revised:2014-04-25 Online:2014-09-25 Published:2014-05-07
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21003018).

以氯化铟为催化剂,通过芳基腈和叠氮化钠的[3+2]环加成反应合成了一系列5-芳基四氮唑,含各种官能团的底物都可以获得高产率. 此合成方法还对酯的分解有催化效果,可以在合成四氮唑的同时对酯进行脱保护获得羧酸和醇.

关键词: 氯化铟, 催化, 四氮唑, 合成, [3+2]环加成, 酯分解

5-Phenyl-1H-tetrazoles were synthesized by catalytic [3+2] cycloaddition with aryl nitriles and sodium azide. Indium trichloride was used as an efficient catalyst. The tetrazoles binding with varieties of functional groups were synthesized in good to quantitative yields. This tetrazole synthetic protocol also showed remarkable de-carboxylation activity. Esters were cleaved to carboxylic acids or alcohols in one pot.

Key words: indium trichloride, catalysis, tetrazole, synthesis, [3+2] cycloaddition, cleavage of ester