苯并[a]咔唑

苯並[a]咔唑
別名	11H-苯並[a]咔唑
識別
CAS號	239-01-0
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
熔點	230-231 °C
	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、鄰菲囉啉和碳酸銀催化下於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

^ ^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
^ 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.
^ J. Org. Chem. 2009, 74, 12, 4490–4498. doi:10.1021/jo9006249
^ 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.
^ 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.

[jacs-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.

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