One-Pot Access to Benzo[a]carbazoles via Palladium(II)-Catalyzed Hetero- and Carboannulations
作者： Moumita Jash , Bimolendu Das , Chinmay Chowdhury
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摘要: A Pd(II)-catalyzed direct synthesis of benzo[a]carbazoles has been achieved through aminopalladation alkynes, followed by intramolecular nucleophilic addition the generated carbon–palladium bond to a tethered cyano/aldehyde group. Compared literature procedures, this synthetic approach is operationally simple, uses simple substrates, and offers fast assembly resulting in which wide variation substituents at different sites well-tolerated, leaving enough opportunity for diversification.
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Biswajit Chakraborty, Debasmita Dutta, Sanjukta Mukherjee, Supriya Das, Nakul C. Maiti, Padma Das, Chinmay Chowdhury, Synthesis and biological evaluation of a novel betulinic acid derivative as an inducer of apoptosis in human colon carcinoma cells (HT-29) European Journal of Medicinal Chemistry. ,vol. 102, pp. 93- 105 ,(2015) , 10.1016/J.EJMECH.2015.07.035
Sanjay Kumar Ghosh, Bing-Chiuan Kuo, Hsiang-Yu Chen, Jia-Ying Li, Shuang-De Liu, Hon Man Lee, Double C–H Functionalization to Construct Polycyclic Heteroarenes Catalyzed by an Ionic Salt of a Pd Complex with an N‐Heterocyclic Carbene Ligand European Journal of Organic Chemistry. ,vol. 2015, pp. 4131- 4142 ,(2015) , 10.1002/EJOC.201500417
Priyanka Kundu, Amrita Mondal, Bimolendu Das, Chinmay Chowdhury, A Straightforward Approach for the Stereoselective Synthesis of (E)-2-Aryl/vinylmethylidene-1,4-benzodiazepines and -1,4-benzodiazepin-5-ones through Palladium/Charcoal-Catalyzed Reactions Advanced Synthesis & Catalysis. ,vol. 357, pp. 3737- 3752 ,(2015) , 10.1002/ADSC.201500661
Lijun Wu, Hui Huang, Pan Dang, Yun Liang, Shaofeng Pi, Construction of benzo[a]carbazole derivatives via Diels–Alder reaction of arynes with vinylindoles RSC Advances. ,vol. 5, pp. 64354- 64357 ,(2015) , 10.1039/C5RA11025D
Jinmao You, Wenchen Zhao, Lingjun Liu, Xianen Zhao, Yourui Suo, Honglun Wang, Yulin Li, Chenxu Ding, Determination of amines using 2-(11H-benzo[a]carbazol-11-yl) ethyl chloroformate (BCEC-Cl) as labeling reagent by HPLC with fluorescence detection and identification with APCI/MS. Talanta. ,vol. 72, pp. 914- 925 ,(2007) , 10.1016/J.TALANTA.2006.12.020
Sylvia Kirchberg, Satoshi Tani, Kirika Ueda, Junichiro Yamaguchi, Armido Studer, Kenichiro Itami, Oxidative biaryl coupling of thiophenes and thiazoles with arylboronic acids through palladium catalysis: otherwise difficult C4-selective C-H arylation enabled by boronic acids. Angewandte Chemie. ,vol. 50, pp. 2387- 2391 ,(2011) , 10.1002/ANIE.201007060
Phil B. Alper, Thomas H. Marsilje, Daniel Mutnick, Wenshuo Lu, Arnab Chatterjee, Michael J. Roberts, Yun He, Donald S. Karanewsky, Donald Chow, Jianmin Lao, Andrea Gerken, Tove Tuntland, Bo Liu, Jonathan Chang, Perry Gordon, H. Martin Seidel, Shin-Shay Tian, Discovery and biological evaluation of benzo[a]carbazole-based small molecule agonists of the thrombopoietin (Tpo) receptor. Bioorganic & Medicinal Chemistry Letters. ,vol. 18, pp. 5255- 5258 ,(2008) , 10.1016/J.BMCL.2008.08.068
Bimolendu Das, Priyanka Kundu, Chinmay Chowdhury, Facile synthesis of 2-arylmethylindoles and 2-vinylic indoles through palladium-catalyzed heteroannulations of 2-(2-propynyl)aniline and 2-(2-propynyl)tosylanilide Organic and Biomolecular Chemistry. ,vol. 12, pp. 741- 748 ,(2014) , 10.1039/C3OB41961D
Erwin Von Angerer, Jelica Prekajac, Benzo[a]carbazole derivatives. Synthesis, estrogen receptor binding affinities, and mammary tumor inhibiting activity Journal of Medicinal Chemistry. ,vol. 29, pp. 380- 386 ,(1986) , 10.1021/JM00153A013
Yuan Tao, Fei Zhang, Chen-Yu Tang, Xin-Yan Wu, Feng Sha, Direct Assembly of Benzo[a]carbazole-5-carboxylates via a Diels–Alder Reaction with Arynes and 3-Alkenylindoles Asian Journal of Organic Chemistry. ,vol. 3, pp. 1292- 1301 ,(2014) , 10.1002/AJOC.201402152