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苯并[a]咔唑

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苯並[a]咔唑
別名 11H-苯並[a]咔唑
識別
CAS號 239-01-0  checkY
SMILES
 
  • C=1C=CC2=C(C1)C=CC=3C=4C=CC=CC4NC23
性質
化學式 C16H11N
摩爾質量 217.27 g·mol−1
外觀 白色固體[1]
熔點 230-231 °C[1]
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

苯並[a]咔唑是一種稠雜環有機物,化學式為C16H11N。有多種方法可以合成該化合物[2],例如,它可由N-(2-溴苯基)-1-萘胺和叔丁醇鉀在液氨中光照反應製得;[3]2-(1-萘氨基)苯甲酸在乙酸鈀鄰菲囉啉碳酸銀催化下於1,4-二氧六環中脫羧關環,也能得到該化合物。[4]它和NBS反應,可以得到5-溴苯並[a]咔唑。[5]

參考文獻

[編輯]
  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.