Chinese Journal of Organic Chemistry >
Efficient Synthesis of 3,6-Dialkylcarbazole-1-formaldehyde and 3,6-Dialkylcarbazole-1,8-diformaldehyde
Received date: 2021-01-03
Revised date: 2021-01-26
Online published: 2021-02-26
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
Yu Zhao , Yang Liu , Xinxin Wang , Yingying Hong , Yingxiu Man , Jinjun Wang , Jiazhu Li . Efficient Synthesis of 3,6-Dialkylcarbazole-1-formaldehyde and 3,6-Dialkylcarbazole-1,8-diformaldehyde[J]. Chinese Journal of Organic Chemistry, 2021 , 41(6) : 2435 -2444 . DOI: 10.6023/cjoc202101001
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