- Copper-catalyzed tandem aerobic oxidative cyclization for the ynthesis of polysubstituted quinolines via C(sp3)/C(sp2)-H bond functionalization
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One-pot Cu-catalyzed tandem aerobic oxidative cyclization for the synthesis of quinolines from 2-vinylanilines/ 2-arylanilines and 2-methylquinolines via C(sp3)-H/C(sp2)- H bond functionalization has been developed. Dioxygen as an ideal oxidant has been employed for this transformation. The substrates bearing various functional groups perform well in this process and generate the desired products in moderate to good yields.
- Pang, Xiaobo,Wu, Mingzhong,Ni, Jixiang,Zhang, Fuming,Lan, Jingfeng,Chen, Baohua,Yan, Rulong
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- Simple and green synthesis of benzimidazoles and pyrrolo[1,2-: A] quinoxalines via Mamedov heterocycle rearrangement
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A method for the synthesis of coupling compounds of benzimidazoles and pyrrolo[1,2-a]quinoxalines via Mamedov Heterocycle Rearrangement is reported here. This method was conducted at room temperature and only solvent (HOAc) was required. A series of 4-(1H-benzo[d]imidazol-2-yl)pyrrolo[1,2-a]quinoxaline derivatives were obtained in moderate to good yields.
- Li, Shichen,Feng, Lei,Ma, Chen
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p. 9320 - 9323
(2021/06/14)
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- PEG-400 as a carbon synthon: Highly selective synthesis of quinolines and methylquinolines under metal-free conditions
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A metal-free, peroxide-free, and efficient procedure for the highly selective synthesis of quinolines and methylquinolines was reported. The main feature of this method was that the same substrate can produce quinolines and methylquinolines, respectively, under different reaction conditions. PEG-400 was used as both a reactant and solvent in this reaction. The utility of the designed procedure was also demonstrated by the derivatization of the products to bioactive compounds. This journal is
- Ding, Chengcheng,Feng, Kaili,Li, Shichen,Ma, Chen
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p. 5542 - 5548
(2021/08/16)
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- Synthesis of oxazolidinones through ring-opening and annulation of vinylene carbonate with 2-pyrrolyl/indolylanilines under Rh(iii) catalysis
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Herein, we have developed a rhodium-catalyzed C-H functionalization and subsequent intramolecular ring-opening/cyclization of vinylene carbonate with 2-pyrrolyl/indolylanilines, which leads to oxazolidinones in moderate to good yields. In this transformation, vinylene carbonate only eliminates one oxygen atom rather than -CO3 or CO2. Furthermore, some control experiments are conducted to elucidate the reaction mechanism. This journal is
- Hu, Fang-Peng,Zhang, Xue-Guo,Wang, Meng,Wang, He-Song,Huang, Guo-Sheng
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p. 11980 - 11983
(2021/12/01)
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- Terminal methyl as a one-carbon synthon: Synthesis of quinoxaline derivatives: Via radical-type transformation
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An iron-promoted method for the construction of pyrrolo[1,2-a]quinoxaline derivatives has been developed. Ferric chloride served as a promoter and as a Lewis acid in the reaction. Solvents provided the corresponding carbon sources simultaneously. The majority of solvents with terminal methyl groups, including ethers, amines and dimethyl sulfoxide, were reactive in the synthesis of quinoxaline derivatives at a certain yield via C-H(sp3) amination/C-O or C-N (C-S) cleavage. This method was applicable to a wide range of pyrrolo[1,2-a]quinoxaline and indolo[1,2-a]quinazoline substrates.
- Wang, Xinfeng,Liu, Huanhuan,Xie, Caixia,Zhou, Feiyu,Ma, Chen
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supporting information
p. 2465 - 2470
(2020/02/20)
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- KI-Mediated One-Pot Transition-Metal-Rree Synthesis of 4-Phenylpyrrolo[1,2-a]quinoxalines
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An efficient and eco-friendly method for the synthesis of pyrrolo[1,2-a]quinoxalines is presented. Compared to previous methods, this protocol is transition-metal-free and only potassium iodide is required. A series of substituted 4-phenylpyrrolo[1,2-a]quinoxalines are obtained in moderate to good yields.
- Li, Shichen,Xie, Caixia,Chu, Xianglong,Dai, Zhen,Feng, Lei,Ma, Chen
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supporting information
p. 4950 - 4956
(2020/08/10)
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- Copper-Catalyzed Synthesis of Alkyl-Substituted Pyrrolo[1,2- a ]quinoxalines from 2-(1 H -Pyrrol-1-yl)anilines and Alkylboronic Acids
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A radical pathway for the construction of pyrrolo[1,2- a ]quinoxalines by using 2-(1 H -pyrrol-1-yl)anilines and alkylboronic acids has been developed. Features of this process include Cu catalysis, readily accessible starting materials, and simple operat
- Guan, Xin,Yan, Rulong
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p. 359 - 362
(2020/02/27)
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- Ruthenium-Catalyzed Synthesis of Pyrrolo[1,2- A [quinoxaline Derivatives from 1-(2-Aminophenyl)pyrroles and Sulfoxonium Ylides
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A ruthenium-catalyzed [5+1] annulation of 1-(2-aminophenyl)pyrroles with α-carbonyl sulfoxonium ylides is reported. This reaction provides a one-step method for synthesizing pyrrolo[1,2- A [quinoxaline derivatives under ambient conditions. The system proceeds with a short reaction time and a high functional-group tolerance. Notably, this divergent protocol tolerates β-keto sulfoxonium ylides and can be applied to α-ester sulfoxonium ylides. A preliminary study was made of the mechanism of the reaction, and a reaction pathway is proposed.
- Cui, Xin-Feng,Hu, Fang-Peng,Huang, Guo-Sheng,Zhan, Zhen-Zhen,Zhou, Xiao-Qiang
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p. 1205 - 1210
(2020/07/20)
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- TFAA-Catalyzed Annulation Synthesis of Spiro Pyrrolo[1,2-a]quinoxaline Derivatives from 1-(2-Aminophenyl)pyrroles and Benzoquinones/Ketones
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A metal-free trifluorosulfonate anhydride (TFAA)-catalyzed strategy for the synthesis of spiro pyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and benzoquinones/ketones has been developed. With this general method, spiro pyrrolo[1,2-a]quinoxalin
- Ni, Jixiang,Jiang, Yong,Qi, Zhenjie,Yan, Rulong
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p. 2898 - 2902
(2019/08/12)
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- Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C-N and C-C Bond Formation
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A method for the annulation of amines and carboxylic acids to form pharmaceutically relevant azaheterocycles via organophosphorus PIII/PV redox catalysis is reported. The method employs a phosphetane catalyst together with a mild bromenium oxidant and terminal hydrosilane reductant to drive successive C-N and C-C bond-forming dehydration events via the serial action of a catalytic bromophosphonium intermediate. These results demonstrate the capacity of PIII/PV redox catalysis to enable iterative redox-neutral transformations in complement to the common reductive driving force of the PIII/PV couple.
- Lecomte, Morgan,Lipshultz, Jeffrey M.,Kim-Lee, Shin-Ho,Li, Gen,Radosevich, Alexander T.
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supporting information
p. 12507 - 12512
(2019/09/04)
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- Copper-catalyzed tandem aerobic oxidative cyclization for the synthesis of 4-cyanoalkylpyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and cyclobutanone oxime esters
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A copper-catalyzed tandem ring-opening/cyclization reaction for the synthesis of 4-cyanoalkylpyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and cyclobutanone oxime esters has been developed. This reaction involves C-C bond cleavage and C-C and C-N bond constructions with good functional group tolerance. A wide range of products are obtained in moderate to good yields under mild conditions.
- An, Zhenyu,Jiang, Yong,Guan, Xin,Yan, Rulong
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p. 10738 - 10741
(2018/09/29)
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- Synthesis of Fused B-Containing Heterocyclic Compounds and Their Relevant Optical Properties
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A series of fused 4,5-borazaropyrrolo[1,2-a]quinolines have been prepared from potassium organotrifluoroborates and substituted 1-(2-aminophenyl)pyrroles via direct formation of C–B and N–B bonds. The target products were obtained in moderate to high yields under mild conditions. The optical properties of some products were investigated by UV/Vis spectroscopy and spectrofluorometry. Moreover, the influence of structural modification on the spectroscopic and electronic properties was studied by DFT calculations.
- An, Zhenyu,Wu, Mingzhong,Kang, Jie,Ni, Jixiang,Qi, Zhenjie,Yuan, Bingxiang,Yan, Rulong
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supporting information
p. 4812 - 4817
(2018/05/23)
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- Identification of Breast Cancer Inhibitors Specific for G Protein-Coupled Estrogen Receptor (GPER)-Expressing Cells
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Together with estrogen receptors ERα and ERβ, the G protein-coupled estrogen receptor (GPER) mediates important pathophysiological signaling pathways induced by estrogens and is currently regarded as a promising target for ER-negative (ER?) and triple-negative (TN) breast cancer. Only a few selective GPER modulators have been reported to date, and their use in cancer cell lines has often led to contradictory results. Herein we report the application of virtual screening and cell-based studies for the identification of new chemical scaffolds with a specific antiproliferative effect against GPER-expressing breast cancer cell lines. Out of the four different scaffolds identified, 8-chloro-4-(4-chlorophenyl)pyrrolo[1,2-a]quinoxaline 14 c was found to be the most promising compound able to induce: 1) antiproliferative activity in GPER-expressing cell lines (MCF7 and SKBR3), similarly to G15; 2) no effect on cells that do not express GPER (HEK293); 3) a decrease in cyclin D1 expression; and 4) a sustained induction of cell-cycle negative regulators p53 and p21.
- Aiello, Francesca,Carullo, Gabriele,Giordano, Francesca,Spina, Elena,Nigro, Alessandra,Garofalo, Antonio,Tassini, Sabrina,Costantino, Gabriele,Vincetti, Paolo,Bruno, Agostino,Radi, Marco
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p. 1279 - 1285
(2017/09/01)
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- FeCl3-Catalyzed synthesis of pyrrolo[1,2-: A] quinoxaline derivatives from 1-(2-aminophenyl)pyrroles through annulation and cleavage of cyclic ethers
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A straightforward Fe-catalyzed method for the synthesis of pyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and cyclic ethers, which includes functionalization of C(sp3)-H bonds and the construction of C-C and C-N bonds, has been devel
- An, Zhenyu,Zhao, Lianbiao,Wu, Mingzhong,Ni, Jixiang,Qi, Zhenjie,Yu, Guiqin,Yan, Rulong
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p. 11572 - 11575
(2017/10/27)
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- Efficient synthesis of pyrrolo[1,2-: A] quinoxalines catalyzed by a Br?nsted acid through cleavage of C-C bonds
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An efficient and convenient one-pot domino reaction for the direct synthesis of pyrrolo[1,2-a]quinoxalines has been developed. This approach utilizes an imine formation reaction, SEAr reaction and cleavage of C-C bonds catalyzed by a Br?nsted acid. β-Diketones and β-keto esters are both well tolerated to give the corresponding products in moderate to excellent yields.
- Xie, Caixia,Feng, Lei,Li, Wanli,Ma, Xiaojun,Ma, Xinkun,Liu, Yihan,Ma, Chen
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p. 8529 - 8535
(2016/09/28)
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- Discovery of pyrrolo-benzo-1,4-diazines as potent Nav1.7 sodium channel blockers
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A series of pyrrolo-benzo-1,4-diazine analogs have been synthesized and displayed potent Nav1.7 inhibitory activity and moderate selectivity over Nav1.5. The syntheses, structure-activity relationships, and selected pharmacokinetic data of these analogs are described. Compound 41 displayed anti-nociceptive efficacy in the rat CFA pain model at 100 mpk oral dosing.
- Ho, Ginny D.,Tulshian, Deen,Bercovici, Ana,Tan, Zheng,Hanisak, Jennifer,Brumfield, Stephanie,Matasi, Julius,Heap, Charles R.,Earley, William G.,Courneya, Brandy,Jason Herr,Zhou, Xiaoping,Bridal, Terry,Rindgen, Diane,Sorota, Steve,Yang, Shu-Wei
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p. 4110 - 4113
(2014/11/07)
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- Palladium(II)-catalyzed cycloamidination via C(sp2)-H activation and isocyanide insertion
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An efficient method for the synthesis of nitrogen heterocycles containing a cyclic amidine moiety has been developed. The process involves palladium-catalyzed C(sp2)-H activation and isocyanide insertion starting with readily accessible ortho-heteroarene-substituted aniline derivatives under mild conditions. Copyright
- Wang, Yong,Zhu, Qiang
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supporting information; experimental part
p. 1902 - 1908
(2012/09/25)
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- AuI-catalyzed direct hydroamination/hydroarylation and double hydroamination of terminal alkynes
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An efficient method for formal Markownikoff hydroamination/hydroarylation and double hydroamination of terminal alkynes has been developed. For example, treatment of terminal alkynes with amino-aromatics or diamines in the presence of 2-5 mol-% of Ph3PAuNTf2 in toluene at 100°C gave the corresponding products in excellent yields. The method was shown to be applicable to a broad range of substrates and, more importantly, unlike our previously reported method, a tethered hydroxy group in the alkyne is not necessary. The mechanism of the reaction is also discussed.
- Patil, Nitin T.,Lakshmi, Pediredla G.V.V.,Singh, Vipender
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supporting information; experimental part
p. 4719 - 4731
(2010/10/21)
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