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1. One-pot synthesis of benzothiazolones from 2-haloanilines, potassium sulfide and N,N-dimethylformamide | |||
Li Zhengkai,Li Xiaoya,Zhou Xiangge | |||
Chemistry 09 July 2015 | |||
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Abstract:Benzothiazolones represent an important class of compounds found in medicines and pesticides. The traditional synthetic methods to prepare of benzothiazolones usually suffered from the limitation of commercially available starting materials such as substituted o-aminothiophenols, toxic carbonyl sources or multiple steps. In this paper, an efficient Cu-catalyzed one-pot synthesis of benzothiazolones directly from easily available 2-haloanilines, potassium sulfide and N,N-dimethylformamide (DMF) as strating materials has been developed. In this protocol, C-S and C-N bond formation occurs during reactions with yields up to 87% after optimization of reaction conditions, which was CuSO4 (10 mol%), 2,2'-bipyridine (10 mol%), and NaOH (3 equiv) at 120 C for 18 h without inert atmosphere. Electron-donating groups seemed to be beneficial to the catalysis than electron-withdrawing groups, which indicated the electron-donating groups would benefit the nucleophilic attack during reaction. The mechanism studies revealed that the carbonyl group of product came from DMF. | |||
TO cite this article:Li Zhengkai,Li Xiaoya,Zhou Xiangge. One-pot synthesis of benzothiazolones from 2-haloanilines, potassium sulfide and N,N-dimethylformamide[OL].[ 9 July 2015] http://en.paper.edu.cn/en_releasepaper/content/4649429 |
2. A green protocol for synthesis of α-amino phosphonates without catalyst | |||
WANG Xing,CHEN Jian,Francis Verpoort | |||
Chemistry 23 June 2015 | |||
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Abstract:Owing to the various important applications in the filed of agricultural, medicinal and industrial chemistry, the synthesis of α-amino phosphonates have received remarkable attention. An efficient, mild and easy-handle method has been developed for the synthesis of α-aminophosphonates derivatives through a reaction of dialkylphosphites, p-toluenesulfonyl, and anilines in two steps under catalyst-free conditions. | |||
TO cite this article:WANG Xing,CHEN Jian,Francis Verpoort. A green protocol for synthesis of α-amino phosphonates without catalyst[OL].[23 June 2015] http://en.paper.edu.cn/en_releasepaper/content/4647999 |
3. Transition Metal-Free One-Pot Protocol towards Conjugated Arylbutadiynyl Sulfides | |||
WANG Jiancheng,DONG Wanrong,PENG Zhihong,AN Delie | |||
Chemistry 02 June 2015 | |||
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Abstract:An efficient strategy towards conjugated arylbuta-1,3-diynyl sulfides (Ar-C≡C-C≡C-SR) was herein reported. In the newly developed one-pot, three-steps protocol, the synthetically or materially significant arylbuta-1,3-diynyl sulfides were obtained from easily accessible 4-hydrocarbylthio-1-arylbuta-1,3-diones, avoiding usage of expensive terminal aryl acetylenes as substrates or any transition metal complexes as catalysts. The gram-scale experiment of the efficient methodology with acceptable yield afforded a good alternative of industrial interest. | |||
TO cite this article:WANG Jiancheng,DONG Wanrong,PENG Zhihong, et al. Transition Metal-Free One-Pot Protocol towards Conjugated Arylbutadiynyl Sulfides[OL].[ 2 June 2015] http://en.paper.edu.cn/en_releasepaper/content/4646069 |
4. Silver-catalyzed Regio-selective Phosphonylation Reaction of Indoles | |||
ZHANG Yanqin,MIN Zehui,DONG Wanrong,PENG Zhihong,AN Delie | |||
Chemistry 31 May 2015 | |||
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Abstract:A new approach towards 2-phosponylated indoles was herein reported. The oxidative methodology took place selectively in a dehydrogenative coupling manner, furnishing the 2-substituted indoles as the exclusive product in moderate to good yields. The yield was depressed by the addition of TEMPO (2,2,6,6-tetramethyl piperidine 1-oxide), indicating the reaction proceed through the radical pathway. | |||
TO cite this article:ZHANG Yanqin,MIN Zehui,DONG Wanrong, et al. Silver-catalyzed Regio-selective Phosphonylation Reaction of Indoles[OL].[31 May 2015] http://en.paper.edu.cn/en_releasepaper/content/4645759 |
5. An Investigation on Imine Formation Mechanism of Cyclohexanone and Benzylamine with DFT Study: Significant p-Chloro-Substituted and Metal-Assisted Effects | |||
Ruofeng Huang,Xiaohui Zhang,Yan Xiong | |||
Chemistry 23 April 2015 | |||
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Abstract:The imine formation mechanism has been investigated using density functional theory at the B3LYP/6-31G* level. The geometries, energies and frequencies of all stationary points were calculated. Our results indicate quantitively that imine formation mechanism proceeds via nucleophilic attack and water elimination, and metal-assisted imine formation only involves nucleophilic attack to ion pair interaction. From the rate-determining step, p-chloro-benzylamine lows energy barrier by 1.1 kJ/mol, which delivers easier imine formation theoretically and accords with experimental description. The imine formation assisted by titanium tetrachloride and zinc dichloride reduces activation energies to 35.6 and -27.0 kJ/mol, respectively, which suggests higher yield. | |||
TO cite this article:Ruofeng Huang,Xiaohui Zhang,Yan Xiong. An Investigation on Imine Formation Mechanism of Cyclohexanone and Benzylamine with DFT Study: Significant p-Chloro-Substituted and Metal-Assisted Effects[OL].[23 April 2015] http://en.paper.edu.cn/en_releasepaper/content/4639978 |
6. Metal-Free Oxidative Decarbonylative Coupling of Aromatic Aldehydes with Arenes: Direct Access to Biaryls | |||
Ren-Jin Tang,Yang Luo | |||
Chemistry 08 April 2015 | |||
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Abstract:A metal-free oxidative decarbonylative coupling of aromatic aldehydes with electron-rich or electron-deficient arenes to produce biaryl compounds was developed. This novel coupling was proposed to proceed via a non-chain radical homolytic aromatic substitution (HAS) type mechanism, based on the substrates scope, ortho-regioselectivity, radical trapping experiments and DFT calculation studies. The ready availability of aromatic aldehydes and arenes, metal-free conditions should make this coupling attractive for the biaryl synthesis | |||
TO cite this article:Ren-Jin Tang,Yang Luo. Metal-Free Oxidative Decarbonylative Coupling of Aromatic Aldehydes with Arenes: Direct Access to Biaryls[OL].[ 8 April 2015] http://en.paper.edu.cn/en_releasepaper/content/4633108 |
7. Concise Total Synthesis of (±)- Pisiferin | |||
Yulong Li,Liqi Li,Yueming Guo,Zhixiang Xie | |||
Chemistry 02 April 2015 | |||
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Abstract:A concise total synthesis of (±)-pisiferin has been accomplished from α-cycloiral via Suzuki coupling and F-C alkylation as key reaction in five steps with an overall yield of 16%. The feature of this concise strategy is using acetyl group to protect the phenol which could be deprotection in moderate condition to avoid the isomerization of target molecular. This work not only provides a strategy to approach the total synthesis of pisiferin itself but also serves as an additional correlation origin to which many related icetaxane-type diterpenes can be referred. | |||
TO cite this article:Yulong Li,Liqi Li,Yueming Guo, et al. Concise Total Synthesis of (±)- Pisiferin[OL].[ 2 April 2015] http://en.paper.edu.cn/en_releasepaper/content/4636172 |
8. Concise Total Synthesis of (±)-Aspidospermidine | |||
SHE Xuegong,MA Haichen,XIE Xingang,ZHANG weiwei | |||
Chemistry 29 December 2014 | |||
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Abstract:Aspidosperma alkaloids, which comprise more than 250 members, share a common pentacyclic skeleton imbedded in an indoline substructure and many of which have significant biological activities. The unique structure and diverse bioactivities of Aspidosperma alkaloids have attracted much attention of the synthetic community for many years and have remained a focus on extensive research activities to present day. Aspidospermidine (1) was isolated from the leaves and skin of Apocynaceae plants and contains a typical skeleton of indole alkaloids. It also exhibits significantly respiratory stimulant and antibiotic activities. The fundamental structure has been the primary target for most of the efforts toward Aspidosperma alkaloids syntheses and has served as the ideal test case for recent developed synthetic strategies. In this paper (±)-Aspidospermidine (1) has been synthesized from the commercially available 2,3-dihydro-1H-carbazol-4(9H)-one 6 in 10 steps with 20% overall yield. Key step of the strategy is a one-pot carbonyl reduction / iminium formation / intramolecular conjugate addition reaction that may be applied for synthesis of other kind of Aspidosperma alkaloids. | |||
TO cite this article:SHE Xuegong,MA Haichen,XIE Xingang, et al. Concise Total Synthesis of (±)-Aspidospermidine[OL].[29 December 2014] http://en.paper.edu.cn/en_releasepaper/content/4625889 |
9. Synthesis and antitumor activities of novel α-aminophosphonates from alizarin | |||
Gui-yang Yao,Heng-shan Wang | |||
Chemistry 14 October 2014 | |||
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Abstract:The synthesis of new α-aminophosphonates derivatives containing alizarin (6a-6f, 7a-7h) moieties is described. Their inhibitory activities against the NCI-H460, Hct-116, 803, A549 and KB human cancer cell lines were estimated using MTT assay in vitro. The screening results revealed that many compounds exhibited moderate to high levels of antitumor activities against the tested cancer cell lines and that most demonstrated more potent inhibitory activities compared with the commercial anticancer drug 5-fluorouracil. The mechanism of compound 7g was preliminarily investigated by Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining , which indicated that the compound 7g induced apoptosis inNCI-H460 cancer cells. | |||
TO cite this article:Gui-yang Yao,Heng-shan Wang. Synthesis and antitumor activities of novel α-aminophosphonates from alizarin[OL].[14 October 2014] http://en.paper.edu.cn/en_releasepaper/content/4613184 |
10. Brønsted Acid Catalyzed Benzylic C–H Bond Functionalization of Azaarenes: Nucleophilic Addition to Nitroso Compounds | |||
Gao Xu,Yang Luo | |||
Chemistry 23 June 2014 | |||
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Abstract:A practical Brønsted acid promoted benzylic C–H functionalization of 2-alkylazaarenes and nucleophilic addition to nitroso compounds was developed under mild conditions. Switched by Brønsted acids, this method can afford azaarene-2-aldimines, azaarene-2-carbaldehyde or azaarene-2-oximes selectively. No metal, base, oxidant or other additives were required. | |||
TO cite this article:Gao Xu,Yang Luo. Brønsted Acid Catalyzed Benzylic C–H Bond Functionalization of Azaarenes: Nucleophilic Addition to Nitroso Compounds[OL].[23 June 2014] http://en.paper.edu.cn/en_releasepaper/content/4602208 |
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