Chinese Journal of Chemistry

Cover image for Vol. 31 Issue 8

August, 2013

Volume 31, Issue 8

Pages 973–1108

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Full Papers
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      Cover Picture: L-Lysine/imidazole-catalyzed Multicomponent Cascade Reaction: Facile Synthesis of C5-substituted 3-Methylcyclohex-2-enones (Chin. J. Chem. 8/2013) (page 973)

      Ziwei Xiang, Zhiqiang Liu, Yiru Liang, Qi Wu and Xianfu Lin

      Version of Record online: 15 AUG 2013 | DOI: 10.1002/cjoc.201390019

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      The cover picture shows a facile and green approach for the direct synthesis of C5-substituted 3-methylcyclohex-2-enones via the Aldol-Robinson cascade reactions. Lysine is the active center of type-I aldolase and could effectively catalyze the aldol reaction between aldehydes and acetones. Inspired by the catalytic mechanism of type-I aldolase, L-lysine/imidazole catalytic system was designed to catalyze the cascade reaction to produce a series of C5-substituted 3-methylcyclohex-2- enones with a versatile aldehyde group with the yields of 16% –92%. The use of simple and readily available materials, mild reaction conditions, simple execution, good yields, and wide synthetic potential of the products, make this new catalytic system attractive for academic research and practical applications. More details are discussed in the article by Lin et al. on page 997–1002.

  2. Contents

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Full Papers
    1. Contents: Chin. J. Chem. 8/2013 (pages 975–980)

      Version of Record online: 15 AUG 2013 | DOI: 10.1002/cjoc.201390020

  3. Communications

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
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    1. Solvent-free Synthesis of Hexagonal Iron Sulfide Nanoflowers (pages 983–986)

      Xia Wang, Wenhui Zhou, Zhixian Chang, Zhengji Zhou and Sixin Wu

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/cjoc.201300341

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      The obtained iron sulfide sample is 3D nanoflowers with an average size of about 160 nm, which consist of many small nanoplates.

    2. Selective Reduction of Nitroarenes with Molybdenum Disulfide (pages 987–991)

      Lei Huang, Pingfei Luo, Man Xiong, Rizhi Chen, Yong Wang, Weihong Xing and Jun Huang

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cjoc.201300310

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      MoS2 was used as a catalyst for the reduction of nitrobenzene under mild conditions. Nitroarenes with halides (F, Cl, Br and I) were reduced selectively without dehaloganation, and functional groups such as NH2, OH, alkene groups were tolerated during the reduction of the nitro compounds. The reduction of p-chloronitrobenzene was studied over MoS2 and Pd/C respectively with hydrazine. p-Chloroaniline was obtained quantitively with MoS2, but some aniline formed by dehaloganation with Pd/C.

  4. Full Papers

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Full Papers
    1. A Highly Efficient Synthesis of Optically Active Ferrocenylethylamines via Hydride Reduction of Chiral Ferrocenylketimines (pages 992–996)

      Hengyu Qian, Shihai Yan, Xiuling Cui, Chao Pi, Cheng Liu and Yangjie Wu

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cjoc.201300211

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      We have developed an efficient and highly stereoselective synthesis of the chiral mono- and bis-ferrocenylamines via sodium borohydride reduction, followed by reductive cleavage of the α-methylbenzyl moiety using 5% Pd/C and HCOONH4. The selectivity was up to 99% de.

    2. On Water: Free Catalysis Approach for the Synthesis of Nitrones from Hydroxamic Acids and Dimethy/Diethyl Acetylenedicarboxylate (pages 1003–1006)

      Jian Li, Yongqin He, Xiaoyu Ren, Xiaokang Shi, Sizhuo Yang, Xiai Gao and Guosheng Huang

      Version of Record online: 19 JUL 2013 | DOI: 10.1002/cjoc.201300400

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      Benzohydroxamic acid reacts with dimethyl acetylenedicarboxylate in the presence of 10 mol% NaOAc to generate (E)-N-(1,4-dimethoxy-1,4-dioxobutan-2-ylidene)-1-phenylcarboxamide oxide in good-to-excellent yield in water at room temperature for 2 h.

    3. Copper(I)-Catalyzed Intramolecular Direct C-Arylation of Azoles with Aryl Bromides (pages 1007–1010)

      Yuan Huang, Wei Chen, Dan Zhao, Chen Chen, Huiqing Yin, Likang Zheng, Ming Jin and Shiqing Han

      Version of Record online: 19 JUL 2013 | DOI: 10.1002/cjoc.201300399

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      A concise route to access 5H-imidazo[2,1-a]isoindole heterofused compounds by copper(I)-catalyzed intramolecular coupling of non-activated aryl bromides with azoles is reported for the first time. With CuI as catalyst, 1,10-phenanthroline as ligand, and K3PO4 as base, the reactions of 1-(2-bromobenzyl)-1H-imidazoles in DMF/o-xylene (1:1, V:V) at 145°C afford the corresponding substituted 5H-imidazo[2,1-a]isoindoles in high yields via intramolecular C-arylation.

    4. Easy One-Pot Synthesis of 1-Monosubstituted Aliphatic 1,2,3-Triazoles from Aliphatic Halides, Sodium Azide and Propiolic Acid by a Click Cycloaddition/Decarboxylation Process (pages 1011–1014)

      Zhongkui Zhang and Chunxiang Kuang

      Version of Record online: 29 MAY 2013 | DOI: 10.1002/cjoc.201300155

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      The synthesis of 1-monosubstituted aliphatic 1,2,3-triazoles was achieved in a one-pot reaction from aliphatic halides (Cl, Br), sodium azide and propiolic acid with yields ranging from moderate to good.

    5. Phase Evolution of Cu[BOND]S System in Ethylene Glycol Solution: the Effect of Anion and PVP on the Transformation of Thiourea (pages 1015–1021)

      Zhen Fang, Chenyan Wang, Fan Fan, Shenghua Hao, Liuyang Long, Yixuan Song and Tingting Qiang

      Version of Record online: 19 JUL 2013 | DOI: 10.1002/cjoc.201300200

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      The effect of anions and PVP on the transition of thiourea in ethylene glycol solution was studied in detail.

    6. Copper(II)-Catalyzed Tandem Synthesis of Substituted 3-Methyleneisoindolin-1-ones (pages 1022–1026)

      Jie Pan, Zhen Xu, Runsheng Zeng and Jianping Zou

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cjoc.201300346

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      An efficient strategy for the synthesis of a variety of 3-methyleneisoindolin-1-ones has been developed. The reaction proceeded from coupling of 2-iodobenzamides (or 2-bromobenzamides) and terminal alkynes via Cu(OAc)2·H2O/2,2′-biimidazole catalyzed in DMF at 60°C and subsequent additive cyclization produced substituted 3-methyleneisoindolin-1-ones in good to excellent yields.

    7. Synthesis of 5,6-Diarylpyridin-2(1H)-ones from Isoflavones (pages 1027–1032)

      Mulin Zhu, Zunting Zhang, Dong Xue, Jinfeng Qiao, Yong Liang and Stanislaw F. Wnuk

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cjoc.201300279

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      A method for the cyclocondensation of substituted isoflavones with cyanoacetamide in the presence of sodium hydroxide to give 3-cyano-5,6-diaryl-2(1H)-pyridones in good yields is reported.

    8. Application of Functionalized N,S-Ketene Acetals–Microwave-Assisted Three-Component Domino Reaction for Rapid Direct Access to Imidazo[1,2-a]pyridines (pages 1033–1038)

      Ming Li, Tengfei Li, Kelong Zhao, Mingda Wang and Lirong Wen

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/cjoc.201300252

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      Imidazo[1,2-a]pyridines have been successfully synthesized in moderate to good yields via a tandem three-component reaction of ethyl 2-(3-oxo-3-arylpropanethioamido)acetates with aromatic aldehydes and malononitrile under microwave irradiation using DABCO as the catalyst. The advantages of this method including high chemo- and regioselectivity make this new strategy highly attractive.

    9. A Highly Diastereoselective Three-component Domino Reaction in Water Yielding Poly-substituted 4,5-Dihydropyrroles (pages 1039–1044)

      Guangjing Tong, Haiwei Xu, Wei Fan, Bo Jiang, Shuliang Wang and Shujiang Tu

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/cjoc.201300249

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      An efficient methodology for the highly diastereoselective synthesis of poly-substituted 4,5-dihydropyrrole derivatives from readily available common reactants in water has been developed. During domino processes, the formation of pyrrole skeleton and its C2-hydroxylation and C3-arylamination were readily achieved via metal-free [3+2] heterocyclization in a one-pot operation.

    10. Iron(III) Chloride Catalyzed Oxidative Coupling Reaction of 1,2-Diarylethylene Derivatives (pages 1045–1053)

      Derong Ji, Lidan Su, Keqing Zhao, Biqin Wang, Ping Hu, Chun Feng, Shikai Xiang, Hua Yang and Chenggang Zhang

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cjoc.201300308

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      An intramolecular oxidative coupling reaction was catalyzed by nontoxic FeCl3 with di-tert-butylperoxide as a sole oxidant at room temperature in CH2Cl2/TFA (9:1 V/V) to give phenanthrenes in good to excellent yields.

    11. Efficient Synthesis of Spiro[furan-3,3′-indoline] Derivatives via Reactions of Pyridinium Salts with Isatinylidene Acetoacetates (pages 1054–1058)

      Zhenming Liu, Jun Fang and Chaoguo Yan

      Version of Record online: 19 JUL 2013 | DOI: 10.1002/cjoc.201300407

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      The functionalized spiro[furan-3,3′-indoline] was developed by domino reactions of pyridinium bromide with isatinylidene acetoacetate in the presence of triethylamine in ethanol at room temperature.

    12. Syntheses, Structures and Properties of Four New Transitional Metal Complexes Based on Benzotriazole-5-carboxylic Acid (pages 1059–1064)

      Yang Li, Changyan Sun, Wenjun Li, Hualei Zhou and Bin Dong

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cjoc.201300213

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      Four new transitional metal complexes were obtained based on benzotriazole-5-carboxylic acid. In these complexes, metal ions are bridged by organic ligands to form 2D layers, which are interlinked by π-π stacking interactions to form supramolecular networks.

    13. Synthesis of Guanidines from Amines and Carbodiimides Catalyzed by Mono-Indenyl-Ligated Rare Earth Metal Bis(silylamide) Complexes (pages 1065–1071)

      Jue Chen, Yibin Wang and Yunjie Luo

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/cjoc.201300302

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      Nucleophilic addition of primary aromatic amines to carbodiimides promoted by the mono-indenyl-ligated rare earth metal bis(silylamide) complexes (C9H6CMe2CH2C5H4N-α)Ln[N(SiHMe2)2]2 afforded a series of guanidines.

    14. Highly Sensitive Fluorometric Assay Method for Acetylcholinesterase Inhibitor Based on Nile Red-Adsorbed Gold Nanoparticles (pages 1072–1078)

      Wenting Han, Shuzhen Liao, Chonghua Zhang, Huazhi Ding, Zhaoyang Wu, Guoli Shen and Ruqin Yu

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/cjoc.201300164

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    15. Theoretical Study on the Hydrogen Bonding Interactions in Complexes of 5-Hydroxytryptamine with Water (pages 1079–1086)

      Lingfei Guo, Zhengguo Huang, Tingting Shen, Lingling Ma and Xiqian Niu

      Version of Record online: 29 MAY 2013 | DOI: 10.1002/cjoc.201300192

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      The hydrogen-bonding interactions in 5-hydroxytryptamine-water (5-HT-H2O) complexes were studied by geometries, harmonic vibrational frequencies, NBO, QTAIM, LMO-EDA at the MP2/6-311++G(d,p) level.

    16. Understanding the Initial Decomposition Pathways of the n-Alkane/Nitroalkane Binary Mixture (pages 1087–1094)

      Yulei Guan, Ying Zhang, Chunhai Yi and Bolun Yang

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cjoc.201300204

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      The mechanism of initial decomposition step of the n-alkane/nitroalkane binary mixture was investigated using quantum chemical calculations. We reveal four initial decomposition pathways and provide insight into the energetic feasibility of all the proposed initial steps.

    17. A Long-Wavelength Fluorescent Probe for Saccharides Based on Boronic-Acid Receptor (pages 1095–1101)

      Hongyan Bai, Qian Sun, Haiyu Tian, Junhong Qian, Lingyi Zhang and Weibing Zhang

      Version of Record online: 17 JUN 2013 | DOI: 10.1002/cjoc.201300269

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      A fluorescent sensor CSP for saccharides was designed and synthesized based on electron transfer mechanism. The conjugation was extended by incorporating an α,β-unsaturated ketone into the coumarin fluorophore. The sensor has good water-solubility, large Stocks shift (≈150 nm) and long emission wavelength (616 nm), which ensure CSP a potential sensor for sugars in biological systems.

    18. Surface Modification of Bituminous Coal and Its Effects on Methane Adsorption (pages 1102–1108)

      Yanyan Feng, Wen Yang, Daijun Liu and Wei Chu

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cjoc.201300215

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