Citation: Zhang Zhiguo, Zheng Dan, Ma Na'na, Bi Jingjing. Brønsted Acid-Promoted the Synthesis of Furo[2, 3-b]quinolines[J]. Chinese Journal of Organic Chemistry, ;2017, 37(7): 1824-1829. doi: 10.6023/cjoc201612032 shu

Brønsted Acid-Promoted the Synthesis of Furo[2, 3-b]quinolines

  • Corresponding author: Zhang Zhiguo, zhangzg@htu.edu.cn
  • Received Date: 8 December 2016
    Revised Date: 19 January 2017
    Available Online: 1 July 2017

    Fund Project: the National Natural Science Foundation of China 21272057the Outstanding Young Talent Cultivation Project Funding of Henan Normal University 14YR002the Key Project of Henan Provincal Educational Committee 14B150042the Young Backbone Teachers Fund of Henan Province 2014GGJS-049the National Natural Science Foundation of China 21372065Project supported by the National Natural Science Foundation of China (Nos. 21272057, 21372065), the Young Backbone Teachers Fund of Henan Province(No. 2014GGJS-049), the Key Project of Henan Provincal Educational Committee (Nos. 14A150019, 14B150042, 15A150015), the Science & Technology Innovation Talents in Universities of Henan Province (No. 17HASTIT002), and the Outstanding Young Talent Cultivation Project Funding of Henan Normal University (No. 14YR002)the Science & Technology Innovation Talents in Universities of Henan Province 17HASTIT002the Key Project of Henan Provincal Educational Committee 15A150015the Key Project of Henan Provincal Educational Committee 14A150019

Figures(4)

  • The furoquinoline unit is present in many natural products. Here, an approach is presented for the preparing of furo[2, 3-b]quinolines from readily available multi-substituted furans in the presence of Brønsted acid via an intramolecular cyclization under the heating conditions. Simple operation, good compatibility, high regioselectivity and morderate yields are the advantages of the method.
  • 加载中
    1. [1]

      (a) Abass, M. Heterocycles 2005, 65, 901.
      (b) Wang, R.; Liu, Z.-Q. Med. Chem. Res. 2013, 22, 1563.
      (c) Huffman, J. W.; Browder, L. E. J. Org. Chem. 1964, 29, 2598.

    2. [2]

      (a) Grougnet, R.; Magiatis, P.; Fokialakis, N.; Mitaku, S.; Skaltsounis, A. L.; Tillequin, F.; Sevenet, T.; Litaudon, M. J. Nat. Prod. 2005, 68, 1083.
      (b) Ambrozin, A. R. P.; Mafezoli, J.; Vieira, P. C.; Fernandes, J. B.; da Silva, M.; Ellena, J. A.; de Albuquerque, S. J. Braz. Chem. Soc. 2005, 16, 434.
      (c) Ito, C.; Itoigawa, M.; Sato, A.; Hasan, C. M.; Rashid, M. A.; Tokuda, H.; Mukainaka, T.; Nishino, H.; Furukawa, H. J. Nat. Prod. 2004, 67, 1488.
      (d) Ayafor, J. F.; Okogun, J. I. J. Chem. Soc., Perkin Trans. 11982, 909.
      (e) Okogun, J. I.; Ayafor, J. F. Chem. Commun. 1977, 652.

    3. [3]

      (a) Mabire, D.; Coupa, S.; Adelinet, C.; Poncelet, A.; Simonnet, Y.; Venet, M.; Wouters, R.; Lesage, A. S. J.; Van Beijsterveldt, L.; Bischoff, F. J. Med. Chem. 2005, 48, 2134.
      (b) Michael, J. P. Nat. Prod. Rep. 2002, 19, 742.
      (c) Michael, J. P. Nat. Prod. Rep. 2004, 21, 650.
      (d) Michael, J. P. Nat. Prod. Rep. 2005, 22, 627.
      (e) Michael, J. P. Nat. Prod. Rep. 2003, 20, 476.

    4. [4]

      Tuppy, H.; Bohm, F. Angew. Chem., Int. Ed. 1956, 68, 388.

    5. [5]

      (a) Yu, L.-Z.; Hu, X.-B.; Xu, Q.; Shi, M. Chem. Commun. 2016, 52, 2701.
      (b) Boyd, D. R.; Sharma, N. D.; Barr, S. A.; Carroll, J. G.; Mackerracher, D.; Malone, J. F. J. Chem. Soc., Perkin Trans. 12000, 3397.

    6. [6]

      (a) Aillaud, I.; Bossharth, E.; Conreaux, D.; Desbordes, P.; Monteiro, N.; Balme, G. Org. Lett. 2006, 8, 1113.
      (b) Sekar, M.; Prasad, K. J. R. J. Nat. Prod. 1998, 61, 294.
      (c) Narasimhan, N. S.; Mali, R. S. Tetrahedron 1974, 30, 4153.
      (d) Collins, J. F.; Gray, G. A.; Grundon, M. F.; Harrison, D. M.; Spyropoulos, C. G. J. Chem. Soc., Perkin Trans. 11973, 94.
      (e) Narasimhan, N. S.; Paradkar, M. V.; Alurkar, R. H. Tetrahedron 1971, 27, 1351.
      (f) Cooke, R. G.; Haynes, H. F. Aust. J. Chem. 1958, 11, 225.
      (g) Grundon, M. F.; McCorkindale, N. J. J. Chem. Soc. 1957, 2177.
      (h) Guo, R.-H.; Zhang, Q.; Ma, Y.-B.; Luo, J.; Geng, C.-A.; Wang, L.-J.; Zhang, X.-M.; Zhou, J.; Jiang, Z.-Y.; Chen, J.-J. Eur. J. Med. Chem. 2011, 46, 307.

    7. [7]

      (a) Nagarajan, R.; Magesh, C. J.; Perumal, P. T. Synth. Stuttg. 2004, 69.
      (b) Yadav, J. S.; Reddy, B. V. S.; Madhuri, C. R.; Sabitha, G. Synth. Stuttg. 2001, 1065.
      (c) Yadav, J. S.; Reddy, B. V. S.; Gayathri, K. U.; Prasad, A. R. Synth. Stuttg. 2002, 2537.

    8. [8]

      Li, X.; Wang, C; Zheng, L. Chin. J. Org. Chem. 2006, 26, 1144(in Chinese).  doi: 10.3321/j.issn:0253-2786.2006.08.024
       

    9. [9]

      (a) Zhang, Z.; Zhang, Q.; Sun, S.; Xiong, T.; Liu, Q. Angew. Chem., Int. Ed. 2007, 46, 1726.
      (b) Ru, T. Light Ind. Sci. Technol. 2013, 5, 58(in Chinese). (茹婷婷, 轻工科技, 2013, 5, 58.)
      (c) Du, W.; Curran, D. P. Org. Lett. 2003, 5, 1765.

    10. [10]

      Zhang, Q.; Zhang, Z.; Yan, Z.; Liu, Q.; Wang, T. Org. Lett. 2007, 9, 3651.  doi: 10.1021/ol701536q

    11. [11]

      Zhang, Z. G. Ph.D. Dissertation, Northeast Normal University, Changchun, 2010(in Chinese).

    12. [12]

      Sai, K. K. S.; Gilbert, T. M.; Klumpp, D. A. J. Org. Chem. 2007, 72, 9761.  doi: 10.1021/jo7013092

    13. [13]

      Heaney, H. In Comprehensive Organic Synthesis, Vol. 2, Eds.:Trost, B. M.; Fleming, I., Pergamon, Oxford, 1991, pp. 733~752.

    14. [14]

      (a) Zhang, Z.; Zhang, Q.; Yan, Z.; Liu, Q. J. Org. Chem. 2007, 72, 9808.
      (b) Xiong, T.; Zhang, Q.; Zhang, Z.; Liu, Q. J. Org. Chem. 2007, 72, 8005.

  • 加载中
    1. [1]

      Yuena Yu Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076

    2. [2]

      Yingchun ZHANGYiwei SHIRuijie YANGXin WANGZhiguo SONGMin WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078

    3. [3]

      Renxiao Liang Zhe Zhong Zhangling Jin Lijuan Shi Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024

    4. [4]

      Xiao XiaoBiao ChenJia-Wei LiJun-Bo ZhengXu WangHang ZhaoFen-Er Chen . Nitrite-catalyzed economic and sustainable bromocyclization of tryptamines/tryptophols to access hexahydropyrrolo[2,3-b]indoles/tetrahydrofuroindolines in batch and flow. Chinese Chemical Letters, 2024, 35(7): 109280-. doi: 10.1016/j.cclet.2023.109280

    5. [5]

      Tianlong Zhang Rongling Zhang Hongsheng Tang Yan Li Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006

    6. [6]

      Huijuan Liao Yulin Xiao Dong Xue Mingyu Yang Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092

    7. [7]

      Xiaofeng Xia Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063

    8. [8]

      Peng XUShasha WANGNannan CHENAo WANGDongmei YU . Preparation of three-layer magnetic composite Fe3O4@polyacrylic acid@ZiF-8 for efficient removal of malachite green in water. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 544-554. doi: 10.11862/CJIC.20230239

    9. [9]

      Yang Chen Peng Chen Yuyang Song Yuxue Jin Song Wu . Application of Chemical Transformation Driven Impurity Separation in Experiments Teaching: A Novel Method for Purification of α-Fluorinated Mandelic Acid. University Chemistry, 2024, 39(6): 253-263. doi: 10.3866/PKU.DXHX202310077

    10. [10]

      Ran Yu Chen Hu Ruili Guo Ruonan Liu Lixing Xia Cenyu Yang Jianglan Shui . 杂多酸H3PW12O40高效催化MgH2储氢. Acta Physico-Chimica Sinica, 2025, 41(1): 2308032-. doi: 10.3866/PKU.WHXB202308032

    11. [11]

      Ruiying WANGHui WANGFenglan CHAIZhinan ZUOBenlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052

    12. [12]

      Xudong Liu Huili Fan Junping Xiao Min Yang Yan Li . Teaching Approaches to the AE + AN Mechanism of Electrophilic Addition Reactions between Olefins and Inorganic Acids in Organic Chemistry. University Chemistry, 2025, 40(7): 367-372. doi: 10.12461/PKU.DXHX202409041

    13. [13]

      Jinghua Wang Yanxin Yu Yanbiao Ren Yesheng Wang . Integration of Science and Education: Investigation of Tributyl Citrate Synthesis under the Promotion of Hydrate Molten Salts for Research and Innovation Training. University Chemistry, 2024, 39(11): 232-240. doi: 10.3866/PKU.DXHX202402057

    14. [14]

      Guangchang YangShenglong YangJinlian YuYishun XieChunlei TanFeiyan LaiQianqian JinHongqiang WangXiaohui Zhang . Regulating local chemical environment in O3-type layered sodium oxides by dual-site Mg2+/B3+ substitution achieves durable and high-rate cathode. Chinese Chemical Letters, 2024, 35(9): 109722-. doi: 10.1016/j.cclet.2024.109722

    15. [15]

      Lina Guo Ruizhe Li Chuang Sun Xiaoli Luo Yiqiu Shi Hong Yuan Shuxin Ouyang Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al2O3催化剂光热催化CO2甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002

    16. [16]

      Yong Wang Yingying Zhao Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009

    17. [17]

      Yinuo Wang Siran Wang Yilong Zhao Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063

    18. [18]

      Liyang ZHANGDongdong YANGNing LIYuanyu YANGQi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079

    19. [19]

      You ZhouLi-Sheng WangShuang-Gui LeiBo-Cheng TangZhi-Cheng YuXing LiYan-Dong WuKai-Lu ZhengAn-Xin Wu . I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799

    20. [20]

      Zhuoyan Lv Yangming Ding Leilei Kang Lin Li Xiao Yan Liu Aiqin Wang Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuOx/TiO2 Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015

Metrics
  • PDF Downloads(6)
  • Abstract views(2006)
  • HTML views(261)

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