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苯并[a]咔唑

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苯并[a]咔唑
别名 11H-苯并[a]咔唑
识别
CAS号 239-01-0  checkY
SMILES
 
  • C=1C=CC2=C(C1)C=CC=3C=4C=CC=CC4NC23
性质
化学式 C16H11N
摩尔质量 217.27 g·mol−1
外观 白色固体[1]
熔点 230-231 °C[1]
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

苯并[a]咔唑是一种稠杂环有机物,化学式为C16H11N。有多种方法可以合成该化合物[2],例如,它可由N-(2-溴苯基)-1-萘胺和叔丁醇钾在液氨中光照反应制得;[3]2-(1-萘氨基)苯甲酸在乙酸钯邻菲啰啉碳酸银催化下于1,4-二氧六环中脱羧关环,也能得到该化合物。[4]它和NBS反应,可以得到5-溴苯并[a]咔唑。[5]

参考文献

  1. ^ 1.0 1.1 Indium-Catalyzed Annulation of 2-Aryl- and 2-Heteroarylindoles with Propargyl Ethers: Concise Synthesis and Photophysical Properties of Diverse Aryl- and Heteroaryl-Annulated[a]carbazoles. J. Am. Chem. Soc. 2008. doi:10.1021/ja803954e
  2. ^ Wu, F., Huang, W., Yiliqi, Yang, J., & Gu, Y. (2018). Relay Catalysis of Bismuth Trichloride and Byproduct Hydrogen Bromide Enables the Synthesis of Carbazole and Benzo[α]carbazoles from Indoles and α-Bromoacetaldehyde Acetals. Advanced Synthesis & Catalysis. doi:10.1002/adsc.201800669. Supporting Information.
  3. ^ J. Org. Chem. 2009, 74, 12, 4490–4498. doi:10.1021/jo9006249
  4. ^ Pd-Catalyzed Decarboxylative Cross-Coupling of N-Aryl Anthranilic Acids to Access Carbazoles: Gram Scale Total Synthesis of Anti- Cancer Drug Ellipticine. Asian Journal of Organic Chemistry. 2023. doi:10.1002/ajoc.202300429.
  5. ^ Shin, Chang Hwan; Kim, Gong Gyeom; Heo, Jeong O; Chun, Min Seung; Kim, Dong Heon. Heterocyclic compounds as organic light-emitting device materials. 2015. KR2015027720.