Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2435-2444.DOI: 10.6023/cjoc202101001 Previous Articles     Next Articles



赵雨a, 刘阳a, 王鑫鑫a, 洪莹莹a, 满英秀a, 王进军b,*(), 李家柱a,*()   

  1. a 烟台大学化学化工学院 山东烟台 264005
    b 烟台大学文经学院 食品与生物工程系 山东烟台 264005
  • 收稿日期:2021-01-03 修回日期:2021-01-26 发布日期:2021-02-26
  • 通讯作者: 王进军, 李家柱
  • 作者简介:
    † 共同第一作者(These authors contributed equally to this work).
  • 基金资助:
    国家自然科学基金(51472212); 山东省自然科学基金(ZR2015BQ012)

Efficient Synthesis of 3,6-Dialkylcarbazole-1-formaldehyde and 3,6-Dialkylcarbazole-1,8-diformaldehyde

Yu Zhaoa, Yang Liua, Xinxin Wanga, Yingying Honga, Yingxiu Mana, Jinjun Wangb(), Jiazhu Lia()   

  1. a College of Chemistry and Chemical Engineering, Yantai University, Yantai, Shandong 264005
    b Department of Food & Biological Engineering, Wenjing College, Yantai University, Yantai, Shandong 264005
  • Received:2021-01-03 Revised:2021-01-26 Published:2021-02-26
  • Contact: Jinjun Wang, Jiazhu Li
  • Supported by:
    National Natural Science Foundation of China(51472212); and the Natural Science Foundation of Shandong Province(ZR2015BQ012)

The currently reported synthesis methods of carbazole-1-formaldehyde or carbazole-1,8-diformaldehyde have some drawbacks, such as long synthetic steps with low yield, high toxicity of reagents, or high risk of operation, which affected the progress of synthesis and application of subsequent derivatives. In this work, the 9-NH of bromocarbazole was protected by 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl), the subsequent formylation was successfully accomplished by n-butyllithium/N,N-dimethylformamide (DMF) instead of tert-butyllithium/DMF to reduce the risk of operation process. Finally, a safe and efficient method that is more suitable for large-scale preparation of 3,6-dialkylcarbazole-1-formaldehyde or 1,8-diformaldehyde was developed. In addition, the reactivity of carbazole-1-formaldehyde or 1,8-diformaldehyde was explored, and a series of tridentate or bidentate ligands were successfully prepared.

Key words: carbazole, formylation, carbazole-1-formaldehyde, carbazole-1, 8-diformaldehyde