Chinese Journal of Chemistry

Cover image for Vol. 33 Issue 3

Early View (Online Version of Record published before inclusion in an issue)

Editors: Guozhen Ji, Shengming Ma

Online ISSN: 1614-7065

Associated Title(s): Chemistry - A European Journal, Chemistry – An Asian Journal, Israel Journal of Chemistry, The Chemical Record

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  1. 1 - 30
  1. Full Papers

    1. Synthesis and Bioactivity of New Chalcone Derivatives as Potential Tyrosinase Activator Based on the Click Chemistry

      Chao Niu, Gen Li, Adila Tuerxuntayi and Haji A. Aisa

      Article first published online: 30 MAR 2015 | DOI: 10.1002/cjoc.201400820

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      A series of new chalcone derivatives which showed activator effect on tyrisinase were synthesized for the first time. Several compounds exhibited better activities than the control drug. Aftert that, the SAR of the compounds was summarized. Besides, several crystal structures of the compounds were got.

    2. Regioselective Oxidation Approaches to Concise Synthesis of (±)-Canabisin D

      Wenling Li, Qian Liu, Hao Liu, Peilan Chen, Xi Yang and Yingying Liu

      Article first published online: 30 MAR 2015 | DOI: 10.1002/cjoc.201500054

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      FeCl3·6H2O-catalyzed oxidative coupling reactions of feruloytyamide protected by tert-butyl or bromine group produced the desired 8-8-coupled aryldihydronaphthalene products, which underwent the debutylation or debromination to concisely synthesize (±)-canabisin D.

    3. Design, Synthesis and Herbicidal Activities of Tetrahydroisoindoline-1,3-dione Derivatives Containing Alkoxycarbonyl Substituted 2-Benzoxazolinone

      Hao Zhang, Kechang Liu, Ruiquan Liu, Qibo Li, Yongqiang Li, Qingmin Wang and Shangzhong Liu

      Article first published online: 30 MAR 2015 | DOI: 10.1002/cjoc.201500046

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      Two series of tetrahydroisoindoline-1,3-diones containing an alkoxycarbonyl substituted 2-benzoxazolinone moiety were designed and synthesized. Compound 1h displayed excellent herbicidal effect against Abutilon theophrasti with ED50 values of 1.8 g AI·ha−1, and compound 1h could potentially be used as a new post-emergence herbicide for maize fields.

    4. Effect of Different Ionic Liquids on 5-Hydroxymethylfurfural Preparation from Glucose in DMA over AlCl3: Experimental and Theoretical Study

      Yan Yang, Wentao Liu, Ningning Wang, Haijun Wang, Wei Li and Zhanxin Song

      Article first published online: 30 MAR 2015 | DOI: 10.1002/cjoc.201500030

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      A series of ionic liquids which possess the same cation and different anions were synthesized to explore the effect of anions on 5-hydroxymethylfurfural (HMF) preparation from glucose over AlCl3. Systematic experiments showed that N-methyl-2-pyrrolidone bromide ([NMP]Br) could promote selective conversion of fructose. Theoretical study indicated that Br could also combine with Al3+, accelerating process of H-shift during glucose isomerization. This discovery can help us choose cocatalysts for low toxic metal, realizing selective conversion of cellulosic biomass conversion.

  2. Communications

    1. Transfer Hydrogenation of Ethyl Levulinate to γ-Valerolactone Catalyzed by Iron Complexes

      Nan Dai, Rui Shang, Mingchen Fu and Yao Fu

      Article first published online: 30 MAR 2015 | DOI: 10.1002/cjoc.201500035

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      The conversion of biomass-derived ethyl levulinate to γ-valerolactone was realized efficiently by utilizing Casey's catalyst and isopropanol via catalytic transfer hydrogenation.

  3. Notes

    1. DBU-Mediated Carboxylative Coupling of Primary Amines, Carbon Dioxide and Propargyl Chlorides

      Wen-Zhen Zhang, Xiang Ren and Xiao-Bing Lu

      Article first published online: 30 MAR 2015 | DOI: 10.1002/cjoc.201500011

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      A carboxylative coupling reaction of various primary amine with propargyl chlorides in the presence of DBU using carbon dioxide as carboxylative reagent was presented.

  4. Full Papers

    1. IBX Oxidation of Benzenedimethanols in the Presence of Cucurbit[8]uril

      Hang Cong, Qiuju Chen, Qingxia Geng, Zhu Tao and Takehiko Yamato

      Article first published online: 30 MAR 2015 | DOI: 10.1002/cjoc.201400886

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      The supramolecular catalysis of Q[8] (cucurbit[8]uril) on the IBX (o-iodoxybenzoic acid) oxidation of o,m,p-benzenedimethanols in aqueous solvent and the host-guest interactions have been investigated.

    2. Siloles and Acetenyl Aromatics Copolymers: Synthesis, Characterization and Photophysical Properties

      Zhenhua He, Guoqiao Lai, Zhifang Li, Xiao Yuan, Yongjia Shen and Chengyun Wang

      Article first published online: 30 MAR 2015 | DOI: 10.1002/cjoc.201400870

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      Copolymers PS-DyCz and PS-DyF were synthesized by Sonogashira coupling reaction.

  5. Communications

    1. Pd(OAc)2/PPh3-Catalyzed Desulfonylative Homocoupling of Arylsulfonyl Chlorides

      Qiao Zhao, Liangshun Chen, Hongyue Lang, Shengying Wu and Limin Wang

      Article first published online: 30 MAR 2015 | DOI: 10.1002/cjoc.201400868

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      The Pd(OAc)2/PPh3-catalyzed desulfonylative homodimerization of arenesulfonyl chlorides as an efficient method for the synthesis of biaryls was described. The corresponding products were obtained in good to excellent yields.

    2. α-Chymotrypsin-Catalyzed Synthesis of Bis(indolyl)alkanes in Water

      Dazhao Sun, Guofang Jiang, Zongbo Xie and Zhanggao Le

      Article first published online: 30 MAR 2015 | DOI: 10.1002/cjoc.201400892

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      A novel methodology for the synthesis of bis(indolyl)methanes by the reaction of aromatic aldehydes and indole in water has been developed, and a series of desired products were obtained in moderate to excellent yields (from 65% to 97%) using 1.2 mg/mL α-chymotrypsin as biocatalyst.

  6. Full Papers

    1. Synthesis of Quaternary α-Hydroxy Phosphonates via Direct Hydroxylation of Phosphonate Compounds

      Jiyan Liu, Wei Wang, Rui Wang and Lijun Gu

      Article first published online: 30 MAR 2015 | DOI: 10.1002/cjoc.201400858

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      It was found for the first time that Cs2CO3 serves as highly efficient catalyst for the direct hydroxylation reactions of phosphonates under mild conditions. This reaction provides an efficient approach to quaternary α-hydroxy phosphonates, which possess intriguing biological activities and are widely used in many areas.

  7. Communications

    1. Supramolecular Self-Assembly of Cucurbit[6]uil and Ionic Liquid in Non-aqueous System

      Xuzhuo Sun, Bo Li, Haibo Zhang and Xiaohai Zhou

      Article first published online: 30 MAR 2015 | DOI: 10.1002/cjoc.201400653

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      A novel pseudorotaxane was synthesized by directly mixing CB[n] with [C4mim]Br, which form 3D structure by aid of hydrogen bonds. The crystal structure demonstrated that CB[6] and [C4mim]Br formed a complex with the ratio 1:1. Besides the bound guest, there were two free ones in the pseudorotaxane as the solvent.

  8. Reviews

    1. An Overview of Self-Assembly and Morphological Regulation of Amphiphilic DNA Organic Hybrids

      Fen Wu, Yiyang Zhang and Zhongqiang Yang

      Article first published online: 30 MAR 2015 | DOI: 10.1002/cjoc.201400846

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      Amphiphilic DNA organic hybrids, containing DNA and organic molecules, e.g., polymer, dendron and lipid, self-assemble into a series of morphologies. Utilizing DNA hybridization, enzymatic activity and secondary structure, the morphologies of assemblies could be precisely regulated.

  9. Full Papers

    1. Synthesis of (R)-(−)-Muscone from (R)-5-Bromo-4-methylpentanoate: A Chiron Approach

      Junwei Shen, Yong Shi and Weisheng Tian

      Article first published online: 9 MAR 2015 | DOI: 10.1002/cjoc.201400862

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      Using methyl (R)-5-bromo-4-methylpentanoate, we have accomplished a synthesis of (R)-muscone, a natural macrocyclic musk, based on chiral pool strategy.

    2. CdTe-paper-based Visual Sensor for Detecting Methyl Viologen

      Yingchun Su, Shenghua Ma, Kunpeng Jiang and Xiaojun Han

      Article first published online: 9 MAR 2015 | DOI: 10.1002/cjoc.201400715

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      The fluorescence microscope images of different methyl viologen concentration (a, 0 µmol/L ; b, 38.89 µmol/L; c, 388.86 µmol/L and d, 3.89 mmol/L) droped onto 50% CdTe-paper-based substrates; e) intensity of the dotted plots from image a to d. The scale bar is 1000 µm.

    3. Efficient Synthesis of Triarylamines Catalyzed by Copper(I) Diazabutadiene Complexes

      Yuhua Liu and Lianming Yang

      Article first published online: 9 MAR 2015 | DOI: 10.1002/cjoc.201400787

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      Cu(I)-(DAB-R) complexes were synthesized and used as catalyst for N-arylation. Cu(I)Cl(DAB-iPP)2 was found to be an efficient catalyst system for N-arylation of diarylamines and anilines with aryl halides, affording the desired products in good to excellent yields.

    4. Fluorescent Recognition of Small Organic Molecules Based on Supramolecular Aggregation/Deaggregation of Planar Cu(II) Coordination Complex

      Liang Hao, Tong Zhang, Ge Chang and Hui Li

      Article first published online: 9 MAR 2015 | DOI: 10.1002/cjoc.201400797

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      The fluorescent properties of a new planar Cu(II) coordination complex with conjugated, rigid and planar ligand in different organic solvents have been studied based on X-ray single-crystal diffraction analysis and the viewpoint of controlling supramolecular aggregation/deaggregation through π-π stacking in different organic solvents.

    5. Hypervalent Iodine(III)-Mediated Benzannulation of Enamines with Alkynes: an Efficient Synthesis of Substituted Aminonaphthoic Acid Derivatives

      Peng Gao, Mingjin Fan, Zijing Bai and Yunyang Wei

      Article first published online: 9 MAR 2015 | DOI: 10.1002/cjoc.201400802

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      An intermolecular two C[BOND]C bond formation procedure for the synthesis of carbocycles mediated by hypervalent iodine(III) reagents was developed.

    6. Syntheses, Cytotoxicity and Properties of CO Releasing Molecules Containing Acetyl Salicylamide-3-pyridine

      Huapeng Liu, Yaguo Gong, Taofeng Zhang, Na Li, Quanyi Zhao, Yonglin Chen, Bin Liu and Yawen Zheng

      Article first published online: 9 MAR 2015 | DOI: 10.1002/cjoc.201400824

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      A series of CO-releasing molecules containing M(CO)5 (M=Mo, W and Cr) were synthesized. Among them, CORMs containing acetyl salicylamide-3-pyridine were evaluated for stability, cytotoxicity, cell cycle and apoptosis.

    7. Lanthanocene Diolate Complexes: Synthesis, Structures and Catalytic Property for ε-Caprolactone Polymerization

      Zhanghai Gu, Li Li, Qianwen Bao and Fugen Yuan

      Article first published online: 9 MAR 2015 | DOI: 10.1002/cjoc.201400826

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      Two lanthanocene diolate complexes were synthesized and structurally characterized. Their catalytic property for the polymerization of ε-caprolactone was studied.

  10. Communications

    1. One-Pot Synthesis of Aliphatic Nitro Compounds by Michael/retro-Claisen Fragmentation Domino Reaction

      Wei Zhang, Yanjing Wang, Cuibing Bai, Jialong Wen and Naixing Wang

      Article first published online: 3 FEB 2015 | DOI: 10.1002/cjoc.201400836

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      A novel and concise method for the direct synthesis of γ-nitro ketones and 1,3-dinitro compounds has been developed. It is the first time to report a domino reaction to synthesize aliphatic nitro compounds via domino Michael/retro-Claisen fragmentation reaction.

  11. Full Papers

    1. Analysis and Identification of the Chemical Constituents of Ding-Zhi-Xiao-Wan Prescription by HPLC-IT-MSn and HPLC-Q-TOF-MS

      Shiyao Tang, Shu Liu, Zhiqiang Liu, Fengrui Song and Shuying Liu

      Article first published online: 3 FEB 2015 | DOI: 10.1002/cjoc.201400789

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      A sequential extraction project, an HPLC-IT-MSn and an HPLC-Q-TOF-MS method were successfully established to separate and identify the constituents of DZXW.

    2. Synthesis of Pyrene-based Planar Conjugated Polymers and the Regioisomers by Intramolecular Cyclization

      Xiaoyan Zhu, Yonggang Wu, Lina Zhou, Yuan Wang, Hongchi Zhao, Baoxiang Gao and Xinwu Ba

      Article first published online: 3 FEB 2015 | DOI: 10.1002/cjoc.201400793

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      Ladder polymers and model compounds were obtained through intramolecular cyclization reaction in the presence of acid from the precursors. The planar polymers and model compounds show untypical UV and PL properties for a rigid, planar, one-dimensional π-system. The regioisomers in intramolecular cyclization reaction can be clearly identified from syn- and anti-structures.

    3. Acceptor-Donor-Acceptor Type Small Molecular Low Band Gap Organic Semiconductors Containing 2-Dicyanomethylen-3-cyano-4,5,5-trimethyl-dihydrofuran

      Sanlong Chen, Xiaolan Qiao, Heping Li and Hongxiang Li

      Article first published online: 3 FEB 2015 | DOI: 10.1002/cjoc.201400811

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      Acceptor-donor-acceptor type compounds with 2-dicyanomethylen-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran, dicyanovinyl and 3-ethyl-2-thioxothiazolidin-4-one as electron acceptors were designed and synthesized. Their physicochemical properties were thoroughly investigated.

    4. Optically Active Helical Poly[(S)-3-vinyl-2,2′-dihydroxy-1,1′-binaphthyl]: New Ligand for Asymmetric Addition of Diethylzinc to Aryl Aldehyde

      Yehui Chen, Guochang Qin, Liwen Yang and Nianfa Yang

      Article first published online: 3 FEB 2015 | DOI: 10.1002/cjoc.201400819

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      The application of helical poly[(S)-3-vinyl-2,2′-dihydroxy-1,1′-binaphthyl] (L*) in the asymmetric addition of diethylzinc to aldehydes has been studied. The catalytic system employing 10 mol% of L* and 150 mol% of Ti(OiPr)4 was found to promote the addition of diethylzinc to a wide range of aromatic aldehydes, giving up to 99% enantiomeric excess (ee) and up to 93% yield of the corresponding secondary alcohol at 0°C. The chiral polymer can be easily recovered and reused without loss of catalytic activity as well as enantioselectivity.

    5. Enantioselective Synthesis of N-Phenyl-dihydropyrano[2,3-c]pyrazoles via Cascade Michael Addition/Thorpe-Ziegler Type Cyclization Catalyzed by a Chiral Squaramide

      Junhua Li and Daming Du

      Article first published online: 3 FEB 2015 | DOI: 10.1002/cjoc.201400829

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      Enantioselective synthesis of biologically active dihydropyrano[2,3-c]pyrazoles has been achieved through a squaramide-catalysed Michael addition/Thorpe-Ziegler type cyclization cascade reaction between arylidenepyrazolones and malononitrile. A series of optically active dihydropyano[2,3-c]pyrazoles were obtained in excellent yields (up to 99%) and moderate to good enantioselectivities (up to 79% ee) under mild reaction conditions.

    6. Synthesis and Catalytic Activity of a Grubbs-Hoveyda Pre-catalyst Having a Trimeric Resting State

      Guiyan Liu, Bin Wu and Jianhui Wang

      Article first published online: 14 JAN 2015 | DOI: 10.1002/cjoc.201400765

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      A Grubbs-Hoveyda pre-catalyst having a trimeric resting state is presented. It was characterized by NMR, HRMS and elemental analysis. Catalytic study for ring-closing metathesis was evaluated. Highly activity for RCM of many substrates was showed.

    7. Towards Reaction Control: An Expeditious Access to Racemic 5-Substituted Tetramates and 5-Substituted Tetramic Acids from Malimides

      Pei-Qiang Huang, Wei Ou and Jian-Liang Ye

      Article first published online: 12 DEC 2014 | DOI: 10.1002/cjoc.201400762

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      A versatile and divergent two-step transformation of malimides to racemic tetramates and tetramic acids is described. The method consists of Grignard reagent addition with malimides, and concentrated HCl-promoted chemoselective transformations of the latter.

    8. Thermal and pH Dual Responsive Copolymer and Silver Nanoparticle Composite for Catalytic Application

      Luqman Ali Shah, Wulian Chen, Mohammad Siddiq, Jianhua Hu, Angang Dong and Dong Yang

      Article first published online: 12 DEC 2014 | DOI: 10.1002/cjoc.201400751

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      Thermal and pH dual responsive P(NIPAM-co-VI) copolymer was used as carriers to load Ag nanoparticles for the first time. The nanoparticles could be stably dispersed at all pH values, and were favorable to be used as a catalyst at a wide pH range, but more efficient at low pH.

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