Citation: Sun Qi, Liu Liyan, Yang Yu, Zha Zhenggen, Wang Zhiyong. Unexpected activated carbon-catalyzed pyrrolo[1, 2-a]quinoxalines synthesis in water[J]. Chinese Chemical Letters, ;2019, 30(7): 1379-1382. doi: 10.1016/j.cclet.2019.04.007 shu

Unexpected activated carbon-catalyzed pyrrolo[1, 2-a]quinoxalines synthesis in water

    * Corresponding author.
    E-mail address: zwang3@ustc.edu.cn (Z. Wang)
  • Received Date: 28 January 2019
    Revised Date: 6 March 2019
    Accepted Date: 3 April 2019
    Available Online: 3 July 2019

Figures(3)

  • An interesting and recyclable activated carbon/water catalytic system for efficient synthesis of pyrrolo[1, 2-a]quinoxaline derivatives was developed. The intramolecular C-N and C-C bond can be easily constructed in water under mild condition. This reaction features a broad substrate scope, a good tolerance to water and air, metal-free, additive-free and redox reagent-free.
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    1. [1]

      (a) S. Butini, R. Budriesi, M. Hamon, et al., J. Med. Chem. 52 (2009) 6946-6950;
      (b) L. Fan, N. Huang, R. Yang, et al., Lett. Drug Des. Discov. 9 (2012) 44-47;
      (c) P. Lin, D.B. Salunke, L. Chen, C. Sun, Org. Biomol. Chem. 9 (2011) 2925-2937;
      (d) J. Guillon, E. Mouray, S. Moreau, et al., Eur. J. Med. Chem. 46 (2011) 2310-2326;
      (e) D.S. Snyder, L. Tradtrantip, C. Yao, M.J. Kurth, A.S. Verkman, J. Med. Chem. 54 (2011) 5468-5477;
      (f) C. Bailly, S. Echepare, F. Gago, Anti-Cancer Drug Des. 14 (1999) 291-303;
      (g) J. Guillon, P. Dallemagne, B. Pfeiffer, et al., Eur. J. Med. Chem. 33 (1998) 293-308;
      (h) T.B. Nguyen, P. Retailleau, A. Al-Mourabit, Org. Lett. 15 (2013) 5238-5241;
      (i) T.B. Nguyen, J.L. Bescont, L. Ermolenko, A. Al-Mourabit, Org. Lett. 15 (2013) 6218-6221.

    2. [2]

      (a) Q. Yuan, D. Ma, J. Org. Chem. 73 (2008) 5159-5162;
      (b) F. Zhao, L. Zhang, H. Liu, S. Zhou, H. liu, Beilstein J. Org. Chem. 9 (2013) 2463-2469;
      (c) J.T. Reeves, D.R. Fandrick, Z. Tan, et al., J. Org. Chem. 75 (2010) 992-994;
      (d) A.K. Verma, R.R. Jha, V.K. Sankar, et al., Eur. J. Org. Chem. 34 (2011) 6998-7010;
      (e) G. Liu, Y. Zhou, D. Lin, et al., ACS Comb. Sci. 13 (2011) 209-213;
      (f) J. Cuillon, I. Forfar, M.M. Matsuda, et al., Bioorg. Med. Chem. 15 (2007) 194-210.

    3. [3]

      M.F. Pereira, V. Thiéry, Org. Lett. 14 (2012) 4754-4757.  doi: 10.1021/ol302006b

    4. [4]

      M. Ramamohan, R. Sridhar, K. Rageavendrarao, et al., Synlett 26 (2015) 1096-1100.  doi: 10.1055/s-0034-1380347

    5. [5]

      (a) N. Mizuno, M. Misono, Chem. Rev. 98 (1998) 199-218;
      (b) R. Akiyama, S. Kobayashi, Chem. Rev. 109 (2009) 594-642;
      (c) S. Ikegami, H. Hamamoto, Chem. Rev. 109 (2009) 583-593;
      (d) M.J. Climent, A. Corma, S. Iborra, Chem. Rev. 111 (2011) 1072-1133 and references therein.

    6. [6]

      (a) Y. Kawashita, N. Nakamichi, H. Kawabata, M. Hayashi, Org. Lett. 4 (2002) 3955-3957;
      (b) H. Sun, F.Z. Su, J. Ni, et al., Angew. Chem. Int. Ed. 48 (2009) 4390-4393;
      (c) N. Kan-nari, S. Okamura, S. Fujita, J. Ozaki, M. Arai, Adv. Synth. Catal. 352 (2010) 1476-1484;
      (d) L. He, Y. Qian, R. Ding, et al., ChemSusChem 5 (2012) 621-624;
      (e) D.T.D. Tang, K.D. Collins, F. Glorius, J. Am. Chem. Soc. 135 (2013) 7450-7453;
      (f) D.T.D. Tang, K.D. Collins, J.B. Ernst, F. Glorius, Angew. Chem. Int. Ed. 53 (2014) 1809-1813;
      (g) S. Fujita, H. Watanabe, A. Katagiri, H. Yoshida, M. Arai, J. Mol. Catal. A: Chem. 393 (2014) 257-262.

    7. [7]

      (a) Z. Zhang, Z. Wang, J. Org. Chem. 71 (2006) 7485-7487;
      (b) J. Zhang, C. Yu, S. Wang, C. Wan, Z. Wang, Chem. Commun. 46 (2010) 5244-5246;
      (c) Y. Wang, G. Ouyang, J. Zhang, Z. Wang, Chem. Commun. 46 (2010) 7912-7914;
      (d) Y. Wang, D. Zhu, L. Tang, S. Wang, Z. Wang, Angew. Chem. Int. Ed. 50 (2011) 8917-8921;
      (e) H. Sun, Y. Zhang, F. Guo, Z. Zha, Z. Wang, J. Org. Chem. 77 (2012) 3563-3569;
      (f) H. Sun, Q. Hua, F. Guo, Z. Wang, W. Huang, Adv. Synth. Catal. 354 (2012) 569-573;
      (g) L. Tang, H. Sun, Y. Li, Z. Zha, Z. Wang, Green Chem. 14 (2012) 3423-3428;
      (h) L. Tang, X. Guo, Y. Li, et al., Chem. Commun. 49 (2013) 5213-5215;
      (i) X. Guo, L. Tang, Y. Yang, Z. Zha, Z. Wang, Green Chem. 16 (2014) 2443-2447;
      (j) L. Tang, X.F. Guo, Y. Yang, Z. Zha, Z. Wang, Chem. Commun. 50 (2014) 6145-6148;
      (k) L. Tang, Y. Yang, L. Wen, S. Zhang, Z. Zha, Z. Wang, Org. Chem. Front. 2 (2015) 114-118.

    8. [8]

      V. Calvino-Casilda, A.J. López-Peinado, C.J. Durán-Valle, R.M. Martín-Aranda, Catal. Rev. Sci. Eng. 52 (2010) 325-380.  doi: 10.1080/01614940.2010.498748

    9. [9]

      (a) Y. Kawashita, N. Nakamichi, H. Kawabata, M. Hayashi, Org. Lett. 5 (2003) 3713-3715;
      (b) Y. Kawashita, M. Hayashi, Molecules 14 (2009) 3073-3093;
      (c) Y. Kawashita, J. Yanagi, T. Fujii, Masahiko Hayashi, Bull. Chem. Soc. Jpn. 82 (2009) 482-488;
      (d) H. Watanabe, S. Asano, S.I. Fujita, H. Yoshida, M. Arai, ACS Catal. 5 (2015) 2886-2894.

    10. [10]

      (a) Y. Yang, L. Tang, S. Zhang, et al., Green Chem. 16 (2014) 4106-4109;
      (b) L. Tang, Y. Yang, L. Wen, X. Yang, Z. Wang, Green Chem. 18 (2016) 1224-1228;
      (c) Y. Yang, S. Zhang, L. Tang, Y. Hu, Z. Zha, Z. Wang, Green Chem. 18 (2016) 2609-2613.

    11. [11]

      (a) C.J. Li, Chem. Rev. 105 (2005) 3095-3166;
      (b) C.J. Li, L. Chen, Chem. Soc. Rev. 35 (2006) 68-82;
      (c) Y.R. Shen, V. Ostroverkhov, Chem. Rev. 106 (2006) 1140-1154;
      (d) C.I. Herrerías, X. Yao, Z. Li, C.J. Li, Chem. Rev. 107 (2007) 2546-2562;
      (e) M. Simon, C.J. Li, Chem. Soc. Rev. 41 (2012) 1415-1427;
      (f) M.B. Gawande, V.D.B. Bonifácio, R. Luque, P.S. Branco, R.S. Varma, Chem. Soc. Rev. 42 (2013) 5522-5551.

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