Citation: Simin Nazari, Mosadegh Keshavarz, Bahador Karami, Nasir Iravani, Masoumeh Vafaee-Nezhad. Imidazol-1-yl-acetic acid as a novel green bifunctional organocatalyst for the synthesis of 1, 8-dioxooctahydroxanthenes under solvent-free conditions[J]. Chinese Chemical Letters, ;2014, 25(2): 317-320. shu

Imidazol-1-yl-acetic acid as a novel green bifunctional organocatalyst for the synthesis of 1, 8-dioxooctahydroxanthenes under solvent-free conditions

  • Corresponding author: Mosadegh Keshavarz, 
  • Received Date: 19 July 2013
    Available Online: 29 November 2013

  • Imidazol-1-yl-acetic acid is introduced as a new, efficient and recyclable green bifunctional organocatalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions. This catalyst is water soluble and can be separated from the products by simple filtration. The filtrate can be evaporated to dryness and recrystallized from cool methanol to give the recovered catalyst. This organocatalyst was used for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions and recycled up to 8 consecutive runs without any losing of its efficiency.
  • 加载中
    1. [1]

      [1] A.M. El-Brashy, M. El-Sayed Metwally, F.A. El-Sepai, Spectrophotometric determination of some fluoroquinolone antibacterials by binary complex formation with xanthene dyes, Farmaco 59 (2004) 809-817.

    2. [2]

      [2] K. Chibale, M. Visser, D.V. Schalkwyk, et al., Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents, Tetrahedron 59 (2003) 2289-2296.

    3. [3]

      [3] B.B. Bhowmik, P. Ganguly, Photophysics of xanthene dyes in surfactant solution, Spectrochim. Acta 61 (2005) 1997-2003.

    4. [4]

      [4] C.G. Knight, T. Stephens, Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Studies in phospholipid vesicles, Biochem. J. 258 (1989) 683-689.

    5. [5]

      [5] M. Ahmad, T.A. King, D.K. Ko, B.H. Cha, J. Lee, Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases, J. Phys. D: Appl. Phys. 35 (2002) 1473-1476.

    6. [6]

      [6] J. Albadi, M. Keshavarz, M. Abedini, M. Khoshakhlagh, Copper iodide nanoparticles on poly(4-vinylpyridine): a new and efficient catalyst for the synthesis of 1,8- dioxooctahydroxanthenes under solvent-free conditions, J. Chem. Sci. 125 (2013) 295-298.

    7. [7]

      [7] M.A. Bigdeli, F. Nemati, G.H. Mahdavinia, H. Doostmohammadi, A series of 1,8- dioxooctahydroxanthenes are prepared using trichloroisocyanuric acid, Chin. Chem. Lett. 20 (2009) 1275-1278.

    8. [8]

      [8] Z. Zhang, P. Zhang, S.H. Yang, H.J. Wang, J. Deng, Multicomponent, solvent-free synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-one derivatives catalyzed by cyanuric chloride, J. Chem. Sci. 122 (2010) 427-432.

    9. [9]

      [9] V. Mirkhani, M. Moghadam, S. Tangestaninejad, I. Mohammadpoor-Baltork, M. Mahdavi, Highly efficient synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes catalysed by carbon-based solid acid under solvent-free conditions, Synth. Commun. 39 (2009) 4328-4340.

    10. [10]

      [10] B. Karami, S.J. Hoseini, K. Eskandari, A. Ghasemi, H. Nasrabadi, Synthesis of xanthene derivatives by employing Fe3O4 nanoparticles as an effective and magnetically recoverable catalyst in water, Catal. Sci. Technol. 2 (2012) 331-338.

    11. [11]

      [11] J. Safaei-Ghomi, M.A. Ghasemzadeh, Zinc oxide nanoparticles: a highly efficient and readily recyclable catalyst for the synthesis of xanthenes, Chin. Chem. Lett. 23 (2012) 1225-1229.

    12. [12]

      [12] J. Mondal, M. Nandi, A. Modak, A. Bhaumik, Functionalized mesoporous materials as efficient organocatalysts for the syntheses of xanthenes, J. Mol. Catal. A: Chem. 363-364 (2012) 254-264.

    13. [13]

      [13] J. Venu-Madhav, Y. Thirupathi-Reddy, P. Narsimha-Reddy, et al., Cellulose sulfuric acid: an efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions, J. Mol. Catal. A: Chem. 304 (2009) 85-87.

    14. [14]

      [14] F. Shirini, N. Ghaffari-Khaligh, Succinimide-N-sulfonic acid: an efficient catalyst for the synthesis of xanthene derivatives under solvent-free conditions, Dyes Pigments 95 (2012) 789-794.

    15. [15]

      [15] R.Z. Wang, L.F. Zhang, Z.S. Cui, Iodine-catalyzed synthesis of 12-aryl-8,9,10,12- tetrahydro-benzo[a]xanthen-11-one derivatives via multicomponent reaction, Synth. Commun. 39 (2009) 2101-2107.

    16. [16]

      [16] A. Zarei, A.R. Hajipour, L. Khazdooz, The one-pot synthesis of 14-aryl or alkyl-14Hdibenzo[a,j]xanthenes catalyzed by P2O5/Al2O3 under microwave irradiation, Dyes Pigments 85 (2010) 133-138.

    17. [17]

      [17] M. Bigdeli, Clean synthesis of 1,8-dioxooctahydroxanthenes promoted by DABCObromine in aqueous media, Chin. Chem. Lett. 21 (2010) 1180-1182.

    18. [18]

      [18] (a) Special issue about organic catalysis, Adv. Synth. Catal. 346 (9-10) (2004) 1007-1249; (b) Hot Topics, Wiley-VCH, Wurttemberg, 2011, This is a selection of recent articles in field of organocatalyst from Angew. Chem, Chem. Eur. J, Eur. J. Org. Chem and Adv. Synth. Catal..

    19. [19]

      [19] T. Okino, Y. Hoashi, Y. Takemoto, Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts, J. Am. Chem. Soc. 125 (2003) 12672-12673.

    20. [20]

      [20] M. Kargar, R. Hekmatshoar, A. Mostashari, Z. Hashemi, Efficient and green synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones using imidazol-1-ylacetic acid as a novel, reusable and water-soluble organocatalyst, Catal. Commun. 15 (2011) 123-126.

    21. [21]

      [21] D. Fang, K. Gong, Z.L. Liu, Synthesis of 1,8-dioxo-octahydroxanthenes catalyzed by acidic ionic liquids in aqueous media, Catal. Lett. 127 (2009) 291-295.

  • 加载中
    1. [1]

      Shuang LiJiayu SunGuocheng LiuShuo ZhangZhong ZhangXiuli Wang . A new Keggin-type polyoxometallate-based bifunctional catalyst for trace detection and pH-universal photodegradation of phenol. Chinese Chemical Letters, 2024, 35(8): 109148-. doi: 10.1016/j.cclet.2023.109148

    2. [2]

      Yue LiMinghao FanConghui WangYanxun LiXiang YuJun DingLei YanLele QiuYongcai ZhangLonglu Wang . 3D layer-by-layer amorphous MoSx assembled from [Mo3S13]2- clusters for efficient removal of tetracycline: Synergy of adsorption and photo-assisted PMS activation. Chinese Chemical Letters, 2024, 35(9): 109764-. doi: 10.1016/j.cclet.2024.109764

    3. [3]

      Meng ShanYongmei YuMengli SunShuping YangMengqi WangBo ZhuJunbiao Chang . Bifunctional organocatalyst-catalyzed dynamic kinetic resolution of hemiketals for synthesis of chiral ketals via hydrogen bonding control. Chinese Chemical Letters, 2025, 36(1): 109781-. doi: 10.1016/j.cclet.2024.109781

    4. [4]

      Meiling XuXinyang LiPengyuan LiuJunjun LiuXiao HanGuodong ChaiShuangling ZhongBai YangLiying Cui . A novel and visible ratiometric fluorescence determination of carbaryl based on red emissive carbon dots by a solvent-free method. Chinese Chemical Letters, 2025, 36(2): 109860-. doi: 10.1016/j.cclet.2024.109860

    5. [5]

      Ze-Yuan MaMei XiaoCheng-Kun LiAdedamola ShoberuJian-Ping ZouS-(1,3-Dioxoisoindolin-2-yl)O,O-diethyl phosphorothioate (SDDP): A practical electrophilic reagent for the phosphorothiolation of electron-rich compounds. Chinese Chemical Letters, 2024, 35(5): 109076-. doi: 10.1016/j.cclet.2023.109076

    6. [6]

      Shaonan Liu Shuixing Dai Minghua Huang . The impact of ester groups on 1,8-naphthalimide electron transport material in organic solar cells. Chinese Journal of Structural Chemistry, 2024, 43(6): 100277-100277. doi: 10.1016/j.cjsc.2024.100277

    7. [7]

      Wu-Yang LiuXin-Xiang LeiWen-Ji WangJun-Mian TianYu-Qi GaoJin-Ming Gao . Hyperforatone A, the 1,8-seco rearranged polycyclic polyprenylated acylphloroglucinol with a unique bicyclo[5.4.0]undecane core from Hypericum perforatum. Chinese Chemical Letters, 2025, 36(4): 110478-. doi: 10.1016/j.cclet.2024.110478

    8. [8]

      Wujun JianMong-Feng ChiouYajun LiHongli BaoSong Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980

    9. [9]

      Chunhua MaMengjiao LiuSiyu OuyangZhenwei CuiJingjing BiYuqin JiangZhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755

    10. [10]

      Qi LiZi-Lu WangYun-He Xu . Copper-catalyzed 1,4-silylcyanation of 1,3-enynes: A silyl radical-initiated approach for synthesis of difunctionalized allenes. Chinese Chemical Letters, 2025, 36(3): 109991-. doi: 10.1016/j.cclet.2024.109991

    11. [11]

      He YaoWenhao JiYi FengChunbo QianChengguang YueYue WangShouying HuangMei-Yan WangXinbin Ma . Copper-catalyzed and biphosphine ligand controlled 3,4-boracarboxylation of 1,3-dienes with carbon dioxide. Chinese Chemical Letters, 2025, 36(4): 110076-. doi: 10.1016/j.cclet.2024.110076

    12. [12]

      Liangfeng YangLiang ZengYanping ZhuQiuan WangJinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685

    13. [13]

      Hai-Yang SongJun JiangYu-Hang SongMin-Hang ZhouChao WuXiang ChenWei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246

    14. [14]

      Xiaohui FuYanping ZhangJuan LiaoZhen-Hua WangYong YouJian-Qiang ZhaoMingqiang ZhouWei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688

    15. [15]

      Peng Wang Daijie Deng Suqin Wu Li Xu . Cobalt-based deep eutectic solvent modified nitrogen-doped carbon catalyst for boosting oxygen reduction reaction in zinc-air batteries. Chinese Journal of Structural Chemistry, 2024, 43(1): 100199-100199. doi: 10.1016/j.cjsc.2023.100199

    16. [16]

      Haodong WangXiaoxu LaiChi ChenPei ShiHouzhao WanHao WangXingguang ChenDan Sun . Novel 2D bifunctional layered rare-earth hydroxides@GO catalyst as a functional interlayer for improved liquid-solid conversion of polysulfides in lithium-sulfur batteries. Chinese Chemical Letters, 2024, 35(5): 108473-. doi: 10.1016/j.cclet.2023.108473

    17. [17]

      Huaixiang YangMiao-Miao LiAijun ZhangJiefei GuoYongqi YuWei Ding . Visible-light-induced photocatalyst- and metal-free radical phosphinoyloximation of alkenes with tert-butyl nitrite as bifunctional reagent. Chinese Chemical Letters, 2025, 36(3): 110425-. doi: 10.1016/j.cclet.2024.110425

    18. [18]

      Yan ZhuJia LiuMeiheng LvTingting WangDongxiang ZhangRong ShangXin-Dong JiangJianjun DuGuiling Wang . Heavy-atom-free orthogonal configurative dye 1,7-di-anthra-aza-BODIPY for singlet oxygen generation. Chinese Chemical Letters, 2024, 35(10): 109446-. doi: 10.1016/j.cclet.2023.109446

    19. [19]

      Kexin YinJingren YangYanwei LiQian LiXing Xu . Metal-free diatomaceous carbon-based catalyst for ultrafast and anti-interference Fenton-like oxidation. Chinese Chemical Letters, 2024, 35(12): 109847-. doi: 10.1016/j.cclet.2024.109847

    20. [20]

      Zhirong YangShan WangMing JiangGengchen LiLong LiFangzhi PengZhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518

Metrics
  • PDF Downloads(0)
  • Abstract views(784)
  • HTML views(19)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return