- Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C-C Bond Cleavage of 2-Arylindoles
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A variety of 2-aminobenzonitriles were prepared from 2-arylindoles in good to excellent yields through tert-butylnitrite (TBN)-mediated nitrosation and sequential iron(III)-catalyzed C-C Bond cleavage in a one-pot fashion. The 2-aminobenzonitriles can be used to rapidly synthesize benzoxazinones by intramolecular condensation. The present method features an inexpensive iron(III) catalyst, gram scalable preparations, and novel C-C bond cleavage of indoles.
- Chen, Wei-Li,Wu, Si-Yi,Mo, Xue-Ling,Wei, Liu-Xu,Liang, Cui,Mo, Dong-Liang
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- Direct Copper-Catalyzed C-3 Arylation of Diphenylphosphine Oxide Indoles
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We have developed a simple and effective method for the C-3 arylation of phosphorus-containing indole compounds in the presence of CuI under mild conditions. This reaction provides a reliable method for the modification of ligands.
- Huang, Xiao-Ling,Li, Chong,Wang, Juan,Yang, Shang-Dong
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supporting information
(2021/10/25)
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- An iron(iii)-catalyzed dehydrogenative cross-coupling reaction of indoles with benzylamines to prepare 3-aminoindole derivatives
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We report a green cascade approach to prepare a variety of 3-aminoindole derivatives in good to excellent yields through an iron(iii)-catalyzed dehydrogenative cross-coupling reaction of 2-arylindoles and primary benzylamines under mild reaction conditions. Mechanistic studies show that a cascade reaction involves a tert-butyl nitrite (TBN)-mediated nitrosation of 2-substituted indoles and a 1,5-hydrogen shift to afford indolenine oximes, sequential iron(iii)-catalyzed condensation and a 1,5-hydrogen shift over four steps in a one-pot reaction. The reaction shows a broad substrate scope of indoles and benzylamines and tolerates a wide range of functional groups. Moreover, the reaction is easily performed at the gram scale without producing waste after the reaction is completed. The 3-aminoindole product is purified by simple extraction, washing, and recrystallization without flash column chromatography. A double imine ligand containing the 3-aminoindole unit is facile to obtain in a 52% yield in one step. The present method highlights readily available starting materials, a simple purification procedure, and the usage of cheap, nontoxic, and environmentally benign iron(iii) catalysts. This journal is
- Chen, Wei-Li,Li, Kun,Liang, Cui,Liang, Wang-Fu,Liao, Wei-Cong,Mo, Dong-Liang,Qiu, Pei-Wen,Su, Gui-Fa
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supporting information
p. 9610 - 9616
(2021/12/09)
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- Antitubercular Activity and Synergistic Study of Novel Pyrazole Derivatives
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A series of 20 novel pyrazole derivatives were designed and prepared, characterized by 1H-NMR, mass spectra (ES-MS), 13C-NMR, and elemental analysis. The synthesized compounds were then evaluated for their growth inhibitory activity
- Jadhav, Sunil B.,Fatema, Samreen,Sanap, Gajanan,Farooqui, Mazahar
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p. 1634 - 1644
(2018/07/24)
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- TEMPO-mediated Aza-diels-alder reaction: Synthesis of tetrahydropyridazines using ketohydrazones and olefins
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A novel, facile, and efficient method for the synthesis of tetrahydropyridazines by a one-pot tandem reaction of easily accessible ketohydrazones and olefins in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) has been successfully developed. The reaction involves the initial generation of azoalkenes from direct oxidative dehydrogenation of ketohydrazones using TEMPO as the commercially available oxidant, followed by a subsequent aza-Diels-Alder reaction with olefins.
- Yang, Xiu-Long,Peng, Xie-Xue,Chen, Fei,Han, Bing
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supporting information
p. 2070 - 2073
(2016/06/09)
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- 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
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A palladium-catalyzed expeditious synthesis of dibenzofused carbazoles from readily available 2-arylindoles and diaryliodonium salts is reported. Interestingly, after the electrophilic C3 palladation of indole, an unexpected "through-space" 1,4-palladium migration to the 2-aryl moiety, by remote C-H bond activation followed by C-H arylation with diaryliodonium salt, and an unprecedented 1,2-aryl shift take place. Finally, an intramolecular cross-dehydrogenative coupling (CDC) at the C2 position affords dibenzo[a,c]carbazoles in high yields. Remarkably, the present migratory annulation occurs through three C-H bond activation one C-C bond cleavage, and the simultaneous construction of three new C-C bonds in a single operation.
- Bhunia, Samir Kumar,Polley, Arghya,Natarajan, Ramalingam,Jana, Ranjan
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supporting information
p. 16786 - 16791
(2015/11/16)
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- Synthesis and biological evaluation of 1,3-diaryl pyrazole derivatives as potential antibacterial and anti-inflammatory agents
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Three series of 1,3-diaryl pyrazole derivatives bearing aminoguanidine or furan-2-carbohydrazide moieties have been synthesized, characterized and evaluated for antibacterial and anti-inflammatory activities. Most of the synthesized compounds showed potent inhibition of several Gram-positive bacterial strains (including multidrug-resistant clinical isolates) and Gram-negative bacterial strains with minimum inhibitory concentration values in the range of 1-64 μg/mL. Compounds 6g, 6l and 7l presented the most potent inhibitory activity against Gram-positive bacteria (e.g. Staphylococcus aureus 4220), Gram-negative bacteria (e.g. Escherichia coli 1924) and the fungus, Candida albicans 7535, with minimum inhibitory concentration values of 1 or 2 μg/mL. Compared with previous studies, these compounds exhibited a broad spectrum of inhibitory activity. Furthermore, compound 7l showed the greatest anti-inflammatory activity (93.59% inhibition, 30 min after intraperitoneal administration), which was more potent than the reference drugs ibuprofen and indomethacin.
- Li, Ya-Ru,Li, Chao,Liu, Jia-Chun,Guo, Meng,Zhang, Tian-Yi,Sun, Liang-Peng,Zheng, Chang-Ji,Piao, Hu-Ri
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p. 5052 - 5057
(2015/11/09)
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- Synthesis of 1-aryl-1H-indazoles via a ligand-free copper-catalyzed intramolecular amination reaction
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A general synthesis of 1-aryl-1-H-indazoles from o-halogenated aryl aldehydes or ketones and aryl hydrazines was described. This protocol included an intermolecular condensation and a ligand-free copper-catalyzed intramolecular Ullmann-type coupling react
- Gao, Mingshan,Liu, Xiujie,Wang, Xianyang,Cai, Qian,Ding, Ke
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experimental part
p. 1199 - 1204
(2012/04/05)
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- Microwave-assisted synthesis of 1-aryl-1H-indazoles via one-pot two-step Cu-catalyzed intramolecular N-arylation of arylhydrazones
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A highly efficient one-pot two-step microwave procedure was developed for the synthesis of 1-aryl-1H-indazoles. Microwave heating of 2-halobenzaldehydes or 2-haloacetophenones with phenylhydrazines at 160°C for 10 min quantitatively yielded the arylhydraz
- Pabba, Chittari,Wang, Hong-Jun,Mulligan, Susan R.,Chen, Zhen-Jia,Stark, Todd M.,Gregg, Brian T.
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p. 7553 - 7557
(2007/10/03)
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- Indole β-Nucleophilic Substitution. Part 7. β-Halogenation of Indoles. Attempted Intramolecular β-Nucleophilic Substitution of α-Arylindoles
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Intramolecular β-nucleophilic substitution of 2-aryl-1-phenylsulphonylindoles could not be achieved.N-Arylsulphonylation of 2-arylindoles with arylsulphonyl halides using phase-transfer conditions is accompanied by 3-halogenation in some cases; the propor
- Dalton, Lesley,Humphrey, Godfred L.,Cooper, Melanie M.,Joule, John A.
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p. 2417 - 2422
(2007/10/02)
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