Chinese Journal of Chemistry

Cover image for Vol. 32 Issue 11

November, 2014

Volume 32, Issue 11

Pages 1085–1182

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Full Papers
    6. Note
    1. You have free access to this content
      Cover Picture: A Versatile Total Synthesis of 8-Oxyberberine and Oxohomoberberines (Chin. J. Chem. 11/2014) (page 1085)

      Yun He, Yang Zheng, Li Hai and Yong Wu

      Article first published online: 14 NOV 2014 | DOI: 10.1002/cjoc.201490024

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      The cover picture shows a new and expeditious approach for the synthesis of 8-oxyberberine and oxohomoberberines. Few general processes existed for the oxohomoberberine from the simple starting material. Reported methods generally required special reagents or complex procedures, and some are limited in scope. The total syntheses of 8-oxyberberine and oxohomoberberines were accomplished starting from commercially available 5-bromobenzo[d][1,3]dioxole, piperonal and sesamol. We have successfully presented a synthetic route for the synthesis of 8-oxyberberine 1a with high total yield of 43% from 5-bromobenzo[d][1,3]dioxole 2a in 7 steps. Meanwhile, we firstly described the synthesis of the oxohomoberberines 1b, 1c and 1d in a 46.2% overall yield (7 steps), a 22.9% overall yield (9 steps), and a 14% overall yield (6 steps), respectively. More details are discussed in the article by Wu et al. on page 1121–1127.

  2. Contents

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Full Papers
    6. Note
    1. Contents: Chin. J. Chem. 11/2014 (pages 1087–1092)

      Article first published online: 14 NOV 2014 | DOI: 10.1002/cjoc.201490025

  3. Communications

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Full Papers
    6. Note
    1. An Efficient Prins Cyclization for Stereoselective Synthesis of Tetrahydropyran from Imines and Homoallyl Alcohols (pages 1095–1098)

      Congrong Liu, Daojuan Cheng and Fulai Yang

      Article first published online: 8 OCT 2014 | DOI: 10.1002/cjoc.201400450

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      An unprecedented protocol has been developed for the efficiend synthesis of substituted tetrahydropyrans via a bismuth-promoted Prins cyclization of imines with homoallyl alcohols. In the presence of 40 mol% BiCl3, a wide variety of imines react smoothly with homoallyl alcohols at room temperature to give the corresponding 4-chlorotetrahydropyran derivatives in good to excellent yields.

    2. A Facile and Practical Process for the Synthesis of Polysubstituted Furans from Alkynes Using Atmospheric Oxygen as a Terminal Oxidant (pages 1099–1102)

      Jingxiu Xu, Xingdong Song and Jinwu Zhao

      Article first published online: 15 SEP 2014 | DOI: 10.1002/cjoc.201400386

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      We present here a facile and practical procedure for the synthesis of tetrasubstituted furans from alkynes catalyzed by palladium acetate together with cupric acetate in acetic acid, using atmospheric oxygen as a terminal oxidant. Various internal aromatic alkynes afforded the target furans in satisfactory yield.

    3. A Facile Approach for Synthesis of Benzofuro[2,3-c]pyridines via Intramolecular Cascade Annulations (pages 1103–1106)

      Ying Duan, Ye Wang and Dongmi Li

      Article first published online: 8 OCT 2014 | DOI: 10.1002/cjoc.201400364

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      A facile and divergent synthesis of benzofuro[2,3-c]pyridines has been achieved under mild conditions through intramolecular cascade annulation. This reaction could efficiently construct pyridine ring and furan ring in one step.

    4. Synthesis of 6-Alkylidene-5,6-dihydro-4H-1,3-thiazine Derivatives via the Cyclization of N-3-Bromo-3-alkenylthioamides (pages 1107–1110)

      Shusu Shen and Yu Liu

      Article first published online: 15 SEP 2014 | DOI: 10.1002/cjoc.201400394

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      Series of 6-alkylidene-5,6-dihydro-4H-1,3-thiazine derivatives were prepared in moderate to good yields. The cyclization is supposed to proceed via both the intramolecular vinylic nucleophilic substitution and the elimination-addition mechanisms (formation of acetylenic intermediates) in a competitive manner.

    5. Synthesis, Crystal Structure of the Receptor Derived from Diethoxycarbonyl Glycoluril for Aromatic Amide Guest (pages 1111–1115)

      Baohan Zhou, Baoming Xu, Li Ma, Meixi Wang, Kun Chen and Yanguo Chen

      Article first published online: 3 NOV 2014 | DOI: 10.1002/cjoc.201400477

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      The receptor derived from the diethoxycarbonyl glycoluril was synthesized and characterized by IR, 1H NMR, Ms and X-ray single crystal analysis. Single crystal X-ray diffraction reveals that the receptor remains monomeric because of its bulky t-Bu groups on the side walls. Its unique binding properties for aromatic amides were studied through 1H NMR and IR.

  4. Full Papers

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Full Papers
    6. Note
    1. A Highly Selective and Turn-on Fluorescent Probe for Fe3+ Ion Based on Perylene Tetracarboxylic Diimide (pages 1116–1120)

      Jinbin Lin, Chunhui Zhu, Xiaoqiong Liu, Bo Chen, Yiyang Zhang, Jinping Xue and Jianyong Liu

      Article first published online: 3 NOV 2014 | DOI: 10.1002/cjoc.201400464

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      A novel perylene tetracarboxylic diimide (PDI)-based fluorescent sensor bearing two bis((1,2,3-triazol-4-yl)methyl)amine (DTA) moieties as receptors has been synthesized and characterized. It is essentially nonfluorescent as a result of photo-induced electron transfer from DTA to PDI. Addition of Fe3+ ions turns on fluorescence of PDI.

    2. A Versatile Total Synthesis of 8-Oxyberberine and Oxohomoberberines (pages 1121–1127)

      Yun He, Yang Zheng, Li Hai and Yong Wu

      Article first published online: 3 NOV 2014 | DOI: 10.1002/cjoc.201400612

      Thumbnail image of graphical abstract

      Few general processes existed for the oxohomoberberine from the simple starting material. Reported methods generally required special reagents or complex procedures, and some are limited in scope. Herein, we described an efficient synthesis of oxohomoberberines by the intramolecular Heck cyclization.

    3. A Novel Efficient Ligand in Anionic Polymerization at Elevated Temperature (pages 1128–1134)

      Bo Chen, Jiming Wang, Minze Shu, Bin Zou, Yong Guan and Anna Zheng

      Article first published online: 15 SEP 2014 | DOI: 10.1002/cjoc.201400351

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      It was confirmed that lithium phenoxide could associate with the active center to block the inserting tunnels in anionic polymerization. With lithium phenoxide, the stability of n-BuLi in THF at 0°C was greatly improved. Due to the steric hindrance effect, the lithium phenoxide could diminish the polymerization rate in the polymerization of both St and MMA. In the polymerization of Ip with lithium phenoxide, it was found that the formations of 1,2- and 1,4-configurations were impeded, while the formation of 3,4-configuration was promoted.

    4. Ring Opening of N-Sulfonyl Aziridines by Amines in Silica-Water (pages 1135–1142)

      Tiantian Li, Xiaosi Ma, Junmei Qi, Feifei Sun and Ning Ma

      Article first published online: 8 OCT 2014 | DOI: 10.1002/cjoc.201400300

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      Ring opening reactions of N-sulfonyl aziridines by primary and secondary amines in silica gel (SG)-water system were achieved. The 1:1 and 2:1 ring opening products were afforded respectively under different conditions. Some 1:1 products can be cyclized with CS2 to synthesize N-sulfonyl cyclothioureas also in water.

    5. Synthesis of Functionalized 1-Benzamido-1,4-dihydropyridines via a One-Pot Two-Step Four-Component Reaction (pages 1143–1150)

      Jing Sun, Guoliang Shen, Yajing Xie and Chaoguo Yan

      Article first published online: 15 SEP 2014 | DOI: 10.1002/cjoc.201400437

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      A one-pot four-component reaction of benzohydrazide, acetylenedicarboxylate, aromatic aldehydes and malononitrile in ethanol with triethylamine as base catalyst afforded functionalized 1-benzamido-1,4-dihydropyridines in satisfactory yields.

    6. Synthesis of Cs2.5H0.5PW12O40/TiO2 Nanocomposites with Dominant TiO2 {001} Facets and Related Photocatalytic Properties (pages 1151–1156)

      Yichen Hu, Yuanhang Ren, Gangfeng Tang, Cheng Wang, Min Tang, Bin Yue and Heyong He

      Article first published online: 15 SEP 2014 | DOI: 10.1002/cjoc.201400383

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      TiO2 nanosheets with dominant {001} facets were coupled with Cs2.5H0.5PW12O40 to produce a highly efficient composite which shows improved photocatalytic activity in the degradation of RhB.

    7. A Novel Dimeric BINOL for Enantioselective Recognition of 1,2-Amino Alcohols (pages 1157–1160)

      Krishnaswamy Velmurugan, Lijun Tang and Raju Nandhakumar

      Article first published online: 15 SEP 2014 | DOI: 10.1002/cjoc.201400321

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      A novel auxillary chiral dimeric binol has been designed, synthesized, and used to enantioselectively recognize 1,2-amino alcohols through the three point of interactions, the reversible imine bond, resonance assisted hydrogen bonding and the hydrogen bonding by the additional chiral moiety introduced at the receptor.

    8. Ultrasensitive and Signal-on Electrochemiluminescence Aptasensor Using the Multi-tris(bipyridine)ruthenium(II)-β-cyclodextrin Complexes (pages 1161–1168)

      Yingying Zhao, Hong Chen, Qiong Chen, Yantao Qi, Fan Yang, Jie Tang, Pingang He and Fan Zhang

      Article first published online: 7 NOV 2014 | DOI: 10.1002/cjoc.201400511

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      An ultrasensitive and signal-on electrochemiluminescence aptasensor to detect target protein (thrombin or lysozyme) was developed using the host-guest recognition between a metallocyclodextrin complex and single-stranded DNA.

    9. Ni(II) Ternary Complex Based on Antimicrobial Drug Enoxacin: Synthesis and Biological Properties (pages 1169–1175)

      Wanyun Huang, Shilin Kong, Zhongchang Wang, Chengxue Pan and Hailiang Zhu

      Article first published online: 8 OCT 2014 | DOI: 10.1002/cjoc.201400420

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      One Ni(II) ternary complex with quinolone drug enoxacin has been synthesized and characterized. The complex can tightly bind to calf-thymus DNA and to human or bovine serum albumin protein.

  5. Note

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Full Papers
    6. Note
    1. Direct Coupling Reaction of Diaryl Methanol with Ketones or Aldehydes Catalyzed by AlCl3 (pages 1176–1182)

      Zhiqiang Zhu, Peng Bai, Tiantian Wang and Zhizhen Huang

      Article first published online: 3 NOV 2014 | DOI: 10.1002/cjoc.201400516

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      A novel coupling reaction of diaryl methanols with ketones or aldehydes has been developed under the catalysis of AlCl3. Various ketones and aldehydes could couple with 9H-xanthen-9-ol smoothly, affording coupling products in 48% –88% yields. A plausible mechanism using AlCl3 to activate both diaryl methanol and ketone or aldehyde is proposed.

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