Citation: Wu Hao, Ma Nana, Song Mengxiao, Zhang Guisheng. Dimethyl sulfoxide-aided copper(0)-catalyzed intramolecular decarbonylative rearrangement of N-aryl isatins leading to acridones[J]. Chinese Chemical Letters, ;2020, 31(6): 1580-1583. doi: 10.1016/j.cclet.2019.10.043 shu

Dimethyl sulfoxide-aided copper(0)-catalyzed intramolecular decarbonylative rearrangement of N-aryl isatins leading to acridones

Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, School of Chemistry and Chemical Engineering, Henan Normal University, Henan 453007, China

mann076@htu.edu.cn

zgs@htu.cn

Received Date: 25 September 2019
Revised Date: 20 October 2019
Accepted Date: 31 October 2019
Available Online: 6 November 2019

Figures(4)

Described here is the first example of Cu(0)-catalyzed intramolecular decarbonylative rearrangements of readily available N-aryl isatins assisted by solvent dimethyl sulfoxide (DMSO) under air atmosphere and additive-free conditions leading to various biologically important acridones in good to excellent yields. This novel transformation is proposed to go through a sequential DMSO-aided Cu insertion into the amide C—N bond, CO extrusion, Cu migration, reductive elimination and DMSO-aided proton migration processes, involving multiple types of bond cleavage and formation in a single chemical step.
- Cu(0)-catalyzed decarbonylation,
- Decarbonylative rearrangements,
- DMSO-aided reactions,
- N-Aryl isatins,
- Acridones
1. [1]
  (a) T. Kondo, Y. Taguchi, Y. Kaneko, M. Niimi, T. Mitsudo, Angew. Chem. Int. Ed. 43 (2004) 5369-5372;
  (b) P. Chen, T. Xu, G. Dong, Angew. Chem. Int. Ed. 53 (2014) 1674-1678;
  (c) T. Kondo, A. Nakamura, T. Okada, et al., J. Am. Chem. Soc. 122 (2000) 6319-6320;
  (d) M. Murakami, H. Amii, K. Shigeto, Y. Ito, J. Am. Chem. Soc. 118 (1996) 8285-8290;
  (e) R. Zeng, G. Dong, J. Am. Chem. Soc. 137 (2015) 1408-1411.
2. [2]
  (a) W. Zhou, Y. Yang, Y. Liu, G.J. Deng, Green Chem. 15 (2013) 76-80;
  (b) J. Yu, H. Yang, Y. Jiang, H. Fu, Chem. -Eur. J. 19 (2013) 4271-4277.
3. [3]
  H. Wu, Z. Zhang, Q. Liu, et al., Org. Lett. 20(2018) 2897-2901. doi: 10.1021/acs.orglett.8b00957
4. [4]
  (a) I.B. Taraporewala, J.W. Cessac, T.C. Chanh, A.V. Delgado, R.F. Schinazi, J. Med. Chem. 35 (1992) 2744-2752;
  (b) O. Tabarrini, G. Manfroni, A. Fravolini, et al., J. Med. Chem. 49 (2006) 2621-2617;
  (c) J.X. Kelly, M.J. Smilkstein, R. Brun, et al., Nature 459 (2009) 270-273.
5. [5]
  T. Faller, K. Hutton, G. Okafo, et al., Chem. Commun. (1997) 1529-1530. doi: 10.1039/A701787A
6. [6]
  D. Zhang, X. Jiang, H. Yang, et al., Org. Biomol. Chem. 11(2013) 3375-3381. doi: 10.1039/c3ob27500k
7. [7]
  (a) X. Ye, P.N. Plessow, M.K. Brinks, et al., J. Am. Chem. Soc. 136 (2014) 5923-5929;
  (b) L.A. Graham, J. Suryadi, T.K. West, G.L. Kucera, U. Bierbach, J. Med. Chem. 55 (2012) 7817-7827.
8. [8]
  S.L. MacNeil, B.J. Wilson, V. Snieckus, Org. Lett. 8(2006) 1133-1136. doi: 10.1021/ol053162e
9. [9]
  J. Wen, S. Tang, F. Zhang, R. Shi, A. Lei, Org. Lett. 19(2017) 94-97. doi: 10.1021/acs.orglett.6b03356
10. [10]
  (a) W. Zhou, Y. Liu, Y. Yang, G.J. Deng, Chem. Commun. 48 (2012) 10678-10680;
  (b) P.C. Huang, K. Parthasarathy, C.H. Cheng, Chem. -Eur. J. 19 (2013) 460-464.
11. [11]
  (a) J. Zhao, R.C. Larock, J. Org. Chem. 72 (2007) 583-588;
  (b) X. Pang, Z. Lou, M. Li, L. Wen, C. Chen, Eur. J. Org. Chem. 15 (2015) 3361-3369.
12. [12]
  (a) Y. Koguchi, J. Kohno, M. Nishio, et al., J. Antibiot. 53 (2000) 105;
  (b) M. Somei, F. Yamada, Nat. Prod. Rep. 20 (2003) 216-242;
  (c) C. Jing, T. Shi, D. Xing, X. Guo, W.H. Hu, Green Chem. 15 (2013) 620-624;
  (d) E.C. Elliott, E.R. Bowkett, J.L. Maggs, et al., Org. Lett. 20 (2011) 5592-5596;
  (e) P. Wu, H. Gao, J. Sun, C.G. Yan, Chin. Chem. Lett. 28 (2017) 329-322;
  (f) K. Stratmann, R.E. Moore, R. Bonjouklian, et al., J. Am. Chem. Soc. 116 (1994) 9935-9942;
  (g) J.L. Jimenez, U. Huber, R.E. Moore, G.M.L. Patterson, J. Nat. Prod. 62 (1999) 569-572;
  (h) H.B. Rasmussen, J.K. Macleod, J. Nat. Prod. 60 (1997) 1152-1154;
  (i) T. Tokunaga, W.E. Hume, T. Umezome, et al., J. Med. Chem. 44 (2001) 4641-4649;
  (j) Z. Xu, S. Zhang, C. Gao, et al., Chin. Chem. Lett. 28 (2017) 159-167;
  (k) R. Shintani, M. Inoue, T. Hayashi, Angew. Chem. Int. Ed. 45 (2006) 3353-3356;
  (l) R. Zeng, G. Dong, J. Am. Chem. Soc. 137 (2015) 1408-1411;
  (m) K. Meena, S. Kumari, J.M. Khurana, et al., Chin. Chem. Lett. 28 (2017) 136-142;
  (n) R.G. Shi, C.G. Yan, Chin. Chem. Lett. 27 (2016) 575-578.
13. [13]
  (a) T. Liu, H. Yang, Y. Jiang, H. Fu, Adv. Synth. Catal. 355 (2013) 1169-1176;
  (b) G.C. Senadi, W.P. Hu, S.S.K. Boominathan, J.J. Wang, Chem. Eur. J. 21 (2015) 998-1003;
  (c) P. Moser, A. Sallmann, I. Wiesenberg, J. Med. Chem. 33 (1990) 2358-2368;
  (d) S. Nizalapur, O. Kimyon, N.N. Biswas, et al., Org. Biomol. Chem. 14 (2016) 680-693;
  (e) P.C. Huang, P. Gandeepan, C.H. Cheng, Chem. Commun. 49 (2013) 8540-8542;
  (f) J. Du, Y. Yang, H. Feng, Y. Li, B. Zhou, Chem. -Eur. J. 20 (2014) 5727-5731;
  (g) P. Qian, J.H. Su, Y. Wang, et al., J. Org. Chem. 82 (2017) 6434-6440;
  (h) A. Ilangovan, G. Satish, Org. Lett. 15 (2013) 5726-5729;
  (i) C. Zhang, S. Li, F. Buress, et al., ACS Catal. 6 (2016) 6853-6860;
  (j) Y. Zi, Z.J. Cai, S.Y. Wang, S.J. Ji, Org. Lett. 16 (2014) 3094-3097;
  (k) J. Luo, S. Gao, Y. Ma, G. Ge, Synlett 29 (2018) 969-973;
  (l) B. Tang, R. Song, C. Wu, et al., J. Am. Chem. Soc. 132 (2010) 8900-8902.
14. [14]
  (a) T.X. Liu, S. Yue, C. Wei, et al., Chem. Commun. 54 (2018) 13331-13334;
  (b) S. Song, X. Li, X. Sun, Y. Yuan, N. Jiao, Green Chem. 17 (2015) 3285-3289;
  (c) Z. Zhang, Q. Tian, J. Qian, et al., J. Org. Chem. 79 (2014) 8182-8188;
  (d) J. Qian, Z. Zhang, Q. Liu, T. Liu, G. Zhang, Adv. Synth. Catal. 356 (2014) 3119-3124.
15. [15]
  M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 09, Revision D.01, Gaussian, Inc., Wallingford, CT, 2013.
16. [16]
  (a) Q.C. Zhang, X. Li, X. Wang, et al., Org. Chem. Front. 6 (2019) 679-687;
  (b) X. Li, S.J. Li, Y. Wang, et al., Catal. Sci. Technol. 9 (2019) 2514-2522.
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