- A rapid, solvent-free, ligandless and mild method for preparing aromatic ketones from acyl chlorides and arylboronic acids via a Suzuki-Miyaura type of coupling reaction
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Aromatic ketones were synthesized via a palladium catalyzed cross-coupling reaction of boronic acids with acyl chlorides in the presence of Na 2CO3 at room temperature under solvent-free conditions. The ligand-free and mild reaction conditions, highly rapid reaction rate and good to excellent yields are important features of this method.
- Bandgar,Patil
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- From Indoles to Carbazoles: Tandem Cp?Rh(III)-Catalyzed C-H Activation/Br?nsted Acid-Catalyzed Cyclization Reactions
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A tandem Cp?Rh(III)-catalyzed C-H activation/Br?nsted acid-catalyzed intramolecular cyclization allows a facile synthesis of carbazoles from readily available indoles. The reaction proceeds under rather mild reaction conditions with the generation of wate
- Wu, Jia-Qiang,Yang, Zhen,Zhang, Shang-Shi,Jiang, Chun-Yong,Li, Qingjiang,Huang, Zhi-Shu,Wang, Honggen
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- Design, synthesis, and evaluation of 9-(pyrimidin-2-yl)-9H-carbazole derivatives disrupting mitochondrial homeostasis in human lung adenocarcinoma
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Since more than 85% of lung cancer cases are non-small cell lung cancer (NSCLC), finding novel agents with anti-tumor activities is meaningful for NSCLC patients. Mitochondria is essential for cellular energy metabolism in cancer, and regulating mitochondrial bioenergetics is emerging as a practical approach for cancer treatment and prevention. The carbazole scaffold is an active structure showing anti-cancer biological activity, and the structural diversity has been expanded through the improvement and optimization of synthesizing methods. To find novel carbazole derivatives with great anti-tumor potential and explore structures variety, we designed and synthesized a series of 9-(pyrimidin-2-yl)-9H-carbazole derivatives based on the previously reported Cp?Rh(III)/H+ tandem catalytic system. With thoroughly bioactivity exploration, we found benzo[d] [1,3]dioxol-5-yl(9-(pyrimidin-2-yl)-9H-carbazol-1-yl)methanone (compound 5n) showed notable activity in disrupting the mitochondrial homeostasis, induced cell cycle arrest and apoptosis in human adenocarcinoma cells, and finally showed anti-tumor activity in an NSCLC-xenograft mice model.
- Chen, Yue-Ru,Li, Kun-Tao,Ou, Tian-Miao,Su, Xiao-Xuan,Sun, Jia-Wei,Wang, Honggen,Wang, Xiao-Na,Wu, Jia-Qiang,Wu, Xiong-Zhi
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- Recent Work on the Synthesis of 3,6-Dibenzoylcarbazole
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By heating carbazole (1) with aluminum trichloride and benzoyl chloride four benzoylcarbazole derivatives were obtained: N-benzoylcarbazole (2), 1-benzoylcarbazole (3), 3-benzoylcarbazole (4) and 3,6-dibenzoylcarbazole (5).The complete characterization of benzoylcarbazole derivatives 2-5 was performed by physical and spectroscopical methods (mp, tlc Rf, glc Tr, uv, ir, 1H nmr, 13C nmr and ms).
- Bonesi, Sergio Mauricio,Erra-Balsells, Rosa
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p. 1035 - 1038
(2007/10/02)
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- STUDIES ON ENAMIDES PART-2 : A NOVEL PHOTOCHEMICAL SYNTHESIS OF 9H-INDOLOPHENANTHRIDIN-9-ONE, A BENZCANTHINE ANALOGUE
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The synthesis of 3-aroylcarbazoles and the unknown 1-aroylcarbazoles has been achieved by the photolysis of 9-aroylcarbazoles in polar solvent.Irradiation of 3(a-c) in non-polar solvent afforded regiospecifically 5(a-c), carbazole (1) and for the first time, 9H-indolophenanthridin-9-one (8) from 3b.The yield of 8 was significantly improved by UV exposure of 9-(2-iodobenzoyl)-carbazole (3e) in methanol and iodine, without providing any photomigrated product.
- Ghosh, Somnath,Datta, Diptendu Bhusan,Datta, Indira,Das, Tapas Kumar
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p. 3775 - 3786
(2007/10/02)
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- Improved Syntheses of Substituted Carbazoles and Benzocarbazoles via Lithiation of the (Dialkylamino)methyl (Aminal)Derivatives
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The lithiation of N-carbazoles occurs readily and exclusively at the protonated carbon adjacent to the nitrogen atom.Reaction with a variety of electrophiles produces good to excellent yields of monosubstituted derivatives.Removal of the lithio-directing and nitrogen-protecting function is readily achieved by mild acid-catalyzed hydrolysis during workup of the reaction.Thus, carbazole undergoes lithiation at the 1-position, dibenzocarbazole at the analogous 6-position, and benzocarbazole at both the 6-and 8-positions, with the former predominating. 1,2,3,4-Tetrahydrocarbazole undergoes lithiation at the 8-position, but with 2,3-dimethylindole reaction occurs at the 2-methyl group.Benzocarbazole fails to form an aminal derivative, but on direct lithiation in ether it can be substituted exclusively at the 1-position of the fused benzene ring.
- Katritzky, Alan R.,Rewcastle, Gordon W.,Vazquez de Miguel, Luis M.
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p. 794 - 799
(2007/10/02)
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- STUDIES ON ENAMIDES. PART- 1 : PHOTOCHEMICAL REARRANGEMENTS OF N-AROYLCARBAZOLES
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The synthesis of 1- and 3-aroylcarbazoles has been achieved by the photolysis of N-aroylcarbazoles alongwith the formation of carbazole and the rearranged product ratio is wavelength dependent.
- Ghosh, Somnath,Das, Tapas Kumar,Datta, Diptendu Bhusan,Mehta, Sangeeta
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p. 4611 - 4614
(2007/10/02)
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