Formal [4 + 2] benzannulation of 2-alkenyl indoles with aldehydes: a route to structurally diverse carbazoles and bis-carbazoles.
作者： Ankush Banerjee , Avishek Guin , Shuvendu Saha , Anushree Mondal , Modhu Sudan Maji
DOI: 10.1039/C8OB02875C
关键词: Reagent 、 Combinatorial chemistry 、 Catalysis 、 Molecular oxygen 、 Chemistry 、 Aromatization
摘要: Construction of structurally diverse carbazoles and bis-carbazoles by protecting-group-free formal [4 + 2]-benzannulation 2-alkenyl indoles aldehydes is demonstrated. The sequence four different reactions executed in one-pot using readily available cheap bottle reagents as catalysts rendering this method attractive. incorporation inexpensive environmentally benign molecular oxygen the oxidant into final aromatization step enables tolerance several functional groups.
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sci-hub.se 参考文章(62)
William M. O'Brien, George F. Bagby, Carprofen: A New Nonsteroidal Antiinflammatory Drug Pharmacology, Clinical Efficacy and Adverse Effects Pharmacotherapy. ,vol. 7, pp. 16- 24 ,(1987) , 10.1002/J.1875-9114.1987.TB03500.X
Tej Narayan Poudel, Yong Rok Lee, Construction of highly functionalized carbazoles via condensation of an enolate to a nitro group Chemical Science. ,vol. 6, pp. 7028- 7033 ,(2015) , 10.1039/C5SC02407B
Samir Kumar Bhunia, Arghya Polley, Ramalingam Natarajan, Ranjan Jana, Through-Space 1,4-Palladium Migration and 1,2-Aryl Shift: Direct Access to Dibenzo[a,c]carbazoles through a Triple C ? H Functionalization Cascade Chemistry: A European Journal. ,vol. 21, pp. 16786- 16791 ,(2015) , 10.1002/CHEM.201503474
Joyeeta Roy, Amit Kumar Jana, Dipakranjan Mal, Recent trends in the synthesis of carbazoles: an update Tetrahedron. ,vol. 68, pp. 6099- 6121 ,(2012) , 10.1016/J.TET.2012.05.007
Benoît Liégault, Doris Lee, Malcolm P. Huestis, David R. Stuart, Keith Fagnou, Intramolecular Pd(II)-catalyzed oxidative biaryl synthesis under air: reaction development and scope. Journal of Organic Chemistry. ,vol. 73, pp. 5022- 5028 ,(2008) , 10.1021/JO800596M
Tomoki Takeuchi, Shinya Oishi, Toshiaki Watanabe, Hiroaki Ohno, Jun-ichi Sawada, Kenji Matsuno, Akira Asai, Naoya Asada, Kazuo Kitaura, Nobutaka Fujii, Structure–Activity Relationships of Carboline and Carbazole Derivatives as a Novel Class of ATP-Competitive Kinesin Spindle Protein Inhibitors Journal of Medicinal Chemistry. ,vol. 54, pp. 4839- 4846 ,(2011) , 10.1021/JM200448N
M.-H. Tsai, Y.-H. Hong, C.-H. Chang, H.-C. Su, C.-C. Wu, A. Matoliukstyte, J. Simokaitiene, S. Grigalevicius, J. V. Grazulevicius, C.-P. Hsu, 3-(9-Carbazolyl)carbazoles and 3,6-Di(9-carbazolyl)carbazoles as Effective Host Materials for Efficient Blue Organic Electrophosphorescence** Advanced Materials. ,vol. 19, pp. 862- 866 ,(2007) , 10.1002/ADMA.200600822
Tinghua Xu, Ran Lu, Xingliang Liu, Peng Chen, Xianping Qiu, Yingying Zhao, None, Porphyrins with four monodisperse oligocarbazole arms: facile synthesis and photophysical properties. Journal of Organic Chemistry. ,vol. 73, pp. 1809- 1817 ,(2008) , 10.1021/JO702426R
Zhanchao Meng, Haixin Yu, Li Li, Wanyin Tao, Hao Chen, Ming Wan, Peng Yang, David J. Edmonds, Jin Zhong, Ang Li, Total synthesis and antiviral activity of indolosesquiterpenoids from the xiamycin and oridamycin families. Nature Communications. ,vol. 6, pp. 6096- 6096 ,(2015) , 10.1038/NCOMMS7096
Carsten Börger, Olga Kataeva, Hans-Joachim Knölker, Novel approach to biscarbazole alkaloids via Ullmann coupling--synthesis of murrastifoline-A and bismurrayafoline-A. Organic and Biomolecular Chemistry. ,vol. 10, pp. 7269- 7273 ,(2012) , 10.1039/C2OB26229K