Citation: Chongjiu Lu, Min Ye, Min Li, Zhijierong Zhang, Yuxin He, Lipeng Long, Zhengwang Chen. Transition-metal-switchable divergent synthesis of nitrile-containing pyrazolo[1, 5-a]pyridines and indolizines[J]. Chinese Chemical Letters, ;2021, 32(12): 3967-3971. doi: 10.1016/j.cclet.2021.04.018 shu

Transition-metal-switchable divergent synthesis of nitrile-containing pyrazolo[1, 5-a]pyridines and indolizines

Key Laboratory of Organo-Pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, China

chenzwang@126.com

Received Date: 8 February 2021
Revised Date: 7 April 2021
Accepted Date: 9 April 2021
Available Online: 16 April 2021

Figures(6)

Palladium-catalyzed oxidative formal [4 + 1] annulation of pyridine-substituted acrylonitriles toward divergent fused N-heterocycles synthesis is reported. The heterodifunctionalization reaction with Cu(OAc)₂ and urea as the nitrogen source accesses to nitrile-substituted pyrazolo[1, 5-a]pyridines in moderate to good yields, while the homodifunctionalization reaction with FeBr₃ leads to synthesis of nitrile-substituted indolizines in excellent yields.
- Divergent synthesis,
- Palladium-catalyzed,
- Annulation reaction,
- Pyrazolo[1, 5-a]pyridines,
- Indolizines
1. [1]
  (a) G. Yan, Y. Zhang, J. Wang, Adv. Synth. Catal. 359 (2017) 4068–4105;
  (b) Y. Ping, Q. Ding, Y. Peng, ACS Catal. 6 (2016) 5989–6005;
  (c) J. Kim, H.J. Kim, S. Chang, Angew. Chem., Int. Ed. 51 (2012) 11948–11959;
  (d) P. Anbarasan, T. Schareina, M. Beller, Chem. Soc. Rev. 40 (2011) 5049–5067;
  (e) G.P. Ellis, T.M. Romney-Alexander, Chem. Rev. 87 (1987) 779–794.
2. [2]
  Y. Wang, Y. Du, N. Huang, Future Med. Chem. 10 (2018) 2713–2727.
3. [3]
  (a) J.T.M. Correia, B. List, F. Coelho, Angew. Chem. Int. Ed. 56 (2017) 7967–7970;
  (b) D. Chandra Mohan, C. Ravi, V. Pappula, et al., J. Org. Chem. 80 (2015) 6846–6855;
  (c) V. Sharma, V. Kumar, Med. Chem. Res. 23 (2014) 3593–3606;
  (d) J.D. Kendall, Curr. Org. Chem. 15 (2011) 2481–2518.
4. [4]
  (a) B. Nie, W. Wu, Y. Zhang, et al., Org. Chem. Front. 7 (2020) 3067–3099;
  (b) B. Sadowski, J. Klajn, D.T. Gryko, Org. Biomol. Chem. 14 (2016) 7804–7828;
  (c) G.S. Singh, E.E. Mmatli, Eur. J. Med. Chem. 46 (2011) 5237–5257.
5. [5]
  (a) V.A. Motornov, A.A. Tabolin, Y.V. Nelyubina, et al., Org. Biomol. Chem. 18 (2020) 1436–1448;
  (b) Q. Huang, D. He, J. Han, et al., Synthesis 50 (2018) 3731–3737;
  (c) X. Yu, S. Ye, J. Wu, Adv. Synth. Catal. 352 (2010) 2050–2056;
  (d) Z. Chen, J. Wu, Org. Lett. 12 (2010) 4856–4859;
  (e) S. Patnaik, H.C. Dietz, W. Zheng, et al., J. Org. Chem. 74 (2009) 8870–8873.
6. [6]
  J.J. Mousseau, J.A. Bull, C.L. Ladd, et al., J. Org. Chem. 76 (2011) 8243–8261, and references cited therein
7. [7]
  (a) D.C. Mohan, C. Ravi, S.N. Rao, et al., Org. Biomol. Chem. 13 (2015) 3556–3560, and references cited therein;
  (b) K.L. Stevens, D.K. Jung, M.J. Alberti, et al., Org. Lett. 7 (2005) 4753–4756.
8. [8]
  O. Obulesu, V. Murugesh, B. Harish, et al., J. Org. Chem. 83 (2018) 6454–6465. doi: 10.1021/acs.joc.8b00746
9. [9]
  (a) G. Yan, Y. Zhang, J. Wang, Adv. Synth. Catal. 359 (2017) 4068–4105;
  (b) K. Alam, S.M. Kim, D.J. Kim, et al., Adv. Synth. Catal. 358 (2016) 2661–2670.
10. [10]
  (a) W. Wang, J. Han, J. Sun, et al., J. Org. Chem. 82 (2017) 2835–2842;
  (b) B. Shen, B. Li, B. Wang, Org. Lett. 18 (2016) 2816–2819;
  (c) J. Brioche, C. Meyer, J. Cossy, Org. Lett. 17 (2015) 2800–2803.
11. [11]
  (a) Y. Shi, V. Gevorgyan, Chem. Commun. 51 (2015) 17166–17169;
  (b) V. Helan, A.V. Gulevich, V. Gevorgyan, Chem. Sci. 6 (2015) 1928–1931;
  (c) S. Chuprakov, F.W. Hwang, V. Gevorgyan, Angew. Chem. Int. Ed 46 (2007) 4757–4759;
  (d) S. Chuprakov, V. Gevorgyan, Org. Lett. 9 (2007) 4463–4466.
12. [12]
  (a) Z. Chen, P. Liang, F. Xu, et al., J. Org. Chem. 84 (2019) 12639–12647;
  (b) X. Wu, P. Zhao, X. Geng, et al., Org. Lett. 19 (2017) 3319–3322;
  (c) Y. Liu, Y. Yu, Y. Fu, et al., Org. Chem. Front. 4 (2017) 2119–2123;
  (d) H. Li, X. Li, Y. Yu, et al., Org. Lett. 19 (2017) 2010–2013;
  (e) S. Tang, K. Liu, Y. Long, et al., Chem. Commun. 51 (2015) 8769–8772;
  (f) S. Tang, K. Liu, Y. Long, et al., Org. Lett. 17 (2015) 2404–2407;
  (g) R.R. Liu, J.J. Hong, C.J. Lu, et al., Org. Lett. 17 (2015) 3050–3053;
  (h) X. Wang, S.Y. Li, Y.M. Pan, et al., Org. Lett. 16 (2014) 580–583.
13. [13]
  (a) J.T. Menezes Correia, B. List, F. Coelho, Angew. Chem., Int. Ed 56 (2017) 7967–7970;
  (b) M.F.Z.J. Amaral, A.A. Baumgartner, R. Vessecchi, et al., Org. Lett. 17 (2015) 238–241;
  (c) Q. Wu, D. Zhao, X. Qin, et al., Chem. Commun. 47 (2011) 9188–9190;
  (d) Y. Yang, K. Cheng, Y. Zhang, Org. Lett. 11 (2009) 5606–5609;
  (e) J.B. Xia, S.L. You, Org. Lett. 11 (2009) 1187–1190.
14. [14]
  (a) X. Li, X. Xie, Y. Liu, J. Org. Chem. 81 (2016) 3688–3699;
  (b) W. Hao, H. Wang, Q. Ye, et al., Org. Lett. 17 (2015) 5674–5677;
  (c) J.H. Lee, I. Kim, J. Org. Chem. 78 (2013) 1283–1288;
  (d) M. Kucukdisli, T. Opatz, J. Org. Chem. 78 (2013) 6670–6676.
15. [15]
  (a) D. Wang, A.B. Weinstein, P.B. White, et al., Chem. Rev. 118 (2018) 2636–2679;
  (b) A.V. Gulevich, A.S. Dudnik, N. Chernyak, et al., Chem. Rev. 113 (2013) 3084–3213;
  (c) J. Wencel-Delord, T. Dröge, F. Liu, et al., Chem. Soc. Rev. 40 (2011) 4740–4761;
  (d) T.W. Lyons, M.S. Sanford, Chem. Rev. 110 (2010) 1147–1169;
  (e) E.M. Beccalli, G. Broggini, M. Martinelli, et al., Chem. Rev. 107 (2007) 5318–5365.
16. [16]
  W. Wu, H. Jiang, Acc. Chem. Res. 45 (2012) 1736–1748. doi: 10.1021/ar3000508
17. [17]
  (a) F.G. Kuruvilla, A.F. Shamji, S.M. Sternson, et al., Nature 416 (2002) 653–657;
  (b) S.L. Schreiber, Science 287 (2000) 1964–1969.
18. [18]
  (a) C. Alonso, E. Martínez de Marigorta, G. Rubiales, et al., Chem. Rev. 115 (2015) 1847–1935;
  (b) J. Wang, M. Sánchez-Roselló, J.L. Aceña, et al., Chem. Rev. 114 (2014) 2432–2506.
19. [19]
  M. Wang, J. Hou, W. Yu, et al., J. Org. Chem. 83 (2018) 14954–14961. doi: 10.1021/acs.joc.8b02022
20. [20]
  S.S. Stahl, Angew. Chem. Int. Ed. 43 (2004) 3400–3420. doi: 10.1002/anie.200300630
21. [21]
  X. Xu, B. Li, Y. Zhao, et al., Org. Chem. Front. 4 (2017) 331–334. doi: 10.1039/C6QO00635C
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2. [2]
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3. [3]
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