Citation: Zheng Xixi, Liu Yunyun, Wan Jie-Ping. Advances in the Synthesis of N-Sulfonyl Amidines[J]. Chinese Journal of Organic Chemistry, ;2020, 40(7): 1891-1900. doi: 10.6023/cjoc202003019 shu

Advances in the Synthesis of N-Sulfonyl Amidines

College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022

Corresponding author: Liu Yunyun, chemliuyunyun@jxnu.edu.cn Wan Jie-Ping, wanjieping@jxnu.edu.cn
Received Date: 8 March 2020
Revised Date: 1 April 2020
Available Online: 11 April 2020
Fund Project: the National Natural Science Foundation of China 21861019Project supported by the National Natural Science Foundation of China (No. 21861019)

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Due to the special gem-nitrogen structure, amidines are important compounds in the synthesis of nitrogen contaning products. As a class of featured amidines, the N-sulfonyl amidines are key intermediates in a number of pivatol organic syntheses, and thus ocuppy significant position in modern organic synthesis. In this context, the research advances on the synthesis of N-sulfonyl amidines are herein reviewed. Based on the key reaction features, the introduction covers the synthetic methods of enamination by tertiary enamine oxidation, amide activation, akyne-azide-amine three-component reaction, enamine carbon-carbon bond functionalization and other related reactions. It is expected that this review will provide guidelines for the reasearch work in related areas.
- N-sulfonyl amidine,
- synthesis,
- amine oxidation,
- amide activation,
- three-component,
- enamine reaction
1. [1]
2. [2]
  (a) Barker, J.; Kilner, M. Coord. Chem. Rev. 1994, 133, 219.
  (b) Nguyen, T. L.; Panchal, R. G.; Topol, I. A.; Lane, D.; Kenny, T.; Burnett, J. C.; Hermone, A. R.; McGrath, C.; Burt, S. K.; Gussio, R.; Bavari, S. J. Mol. Struct. 2007, 821, 139.
  (c) Yuan, J.; Li, J.; Wang, B.; Sun, S.; Cheng, J. Tetrahedron Lett. 2017, 58, 4783.
3. [3]
  (a) Katz, B. A.; Clark, J. M.; Finer-Moore, J. S.; Jenkins, T. E.; Johnson, C. R.; Ross, M. J.; Luong, C.; Moore, W. R.; Stroud, R. M. Nature 1998, 391, 608.
  (b) Kotthaus, J.; Steinmetzer, T.; van de Locht, A.; Clement, B. J. Enzyme Inhib. Med. Chem. 2011, 26, 115.
  (c) Mackman, R. L.; Katz, B. A.; Breitenbucher, J. G.; Hui, H. C.; Verner, E.; Luong, C.; Liu, L.; Sprengeler, P. A. J. Med. Chem. 2001, 44, 3856.
4. [4]
  Lee, M. Y.; Kim, M. H.; Kim, S. H.; Kim, B. T.; Jeong, I. H.; Chang, S.; Kim, H.; Chang, S.-Y. Bioorg. Med. Chem. Lett. 2010, 20, 541. doi: 10.1016/j.bmcl.2009.11.104
5. [5]
  Song, Z. L.; Chen, H.-L.; Wang, Y.-H.; Goto, M.; Gao, W.-J.; Cheng, P.-L.; Morris-Natschke, S. L.; Liu, Y.-Q.; Zhu, G.-X.; Wang, M.-J.; Lee, K.-H. Bioorg. Med. Chem. Lett. 2015, 25, 2690. doi: 10.1016/j.bmcl.2015.04.060
6. [6]
  Suja, T. D.; Divya, K. V. L.; Naik, L. V.; Ravi Kumar, A.; Kamal, A. Bioorg. Med. Chem. Lett. 2016, 26, 2072. doi: 10.1016/j.bmcl.2016.02.071
7. [7]
  Luke, R. O.; Shiao, Y. C. J. Org. Chem. 2017, 82, 2515. doi: 10.1021/acs.joc.6b02894
8. [8]
  (a) Ran, R.-Q.; Xiu, S.-D.; Li, C. Org. Lett. 2014, 16, 6394.
  (b) Nandi, G. C.; Jesin, I. Adv. Synth. Catal. 2018, 360, 2465.
  (c) van Vliet, K. M.; Polak, L. H.; Siegler, M. A.; van der Vlugt, J. I.; Guerra, C. F.; de Bruin, B. J. Am. Chem. Soc. 2019, 141, 15240.
  (d) Aly, A. A.; Brase, S.; Gomaa, M. A.-M. ARKIVOC 2018, vi, 85.
9. [9]
  Xu, X.; Li, X.; Ma, L.; Ye, N.; Weng, B. J. Am. Chem. Soc. 2008, 130, 14048. doi: 10.1021/ja8047514
10. [10]
  Li, X.; Xu, X.; Ge, Z.; Cheng, D.; Ma, L.; Lu, C.; Zhang, Q.; Yao, N.; Li, X. Org. Lett. 2010, 12, 897. doi: 10.1021/ol1000236
11. [11]
  Liu, N.; Tang, B. Y.; Chen, Y.; He, L. Eur. J. Org. Chem. 2009, 2059.
12. [12]
  Bi, W.-Z.; Zhang, W.-J.; Li, Z.-J.; Xia, X.-Y.; Chen, X.-L.; Qu, L.-B.; Zhao, Y.-F. Eur. J. Org. Chem. 2019, 6071.
13. [13]
  Wang, S.; Wang, Z.; Zheng, X. Chem. Commun. 2009, 7372.
14. [14]
  (a) Rouzi, A.; Hudabaierdi, R.; Wusiman, A. Tetrahedron 2018, 74, 2475.
  (b) Jian, Y.; Chen, M.; Yang, C.; Xia, W. Synthesis 2019, 51, 4425.
15. [15]
  Shojaei, S.; Ghasemi Z.; Shahrisa, A. Tetrahedron Lett. 2017, 58, 3957. doi: 10.1016/j.tetlet.2017.08.075
16. [16]
  Gui, J.; Xie, H.; Jiang, H.; Zeng, W. Org. Lett. 2019, 21, 2804. doi: 10.1021/acs.orglett.9b00786
17. [17]
  Ding, R.; Chen, H.; Xu, Y. L.; Tang, H. T.; Chen, Y. Y.; Pan, Y. M. Adv. Synth. Catal. 2019, 361, 3656. doi: 10.1002/adsc.201900359
18. [18]
  Wang, Z.; Zhang, L. Wang, S.; Wan, C.; Zha, Z.; Du, J.; Wang, Z. Chem. Commun. 2011, 47, 5488. doi: 10.1039/c1cc10871a
19. [19]
  Chen, J.; Guo, Y.-P.; Sun, M.-H.; Fan, G.-T.; Zhou, L. Chem. Commun. 2014, 50, 12367. doi: 10.1039/C4CC05578K
20. [20]
  Fusco, R.; Bianchetti, G.; Pocar, D.; Ugo, R. Chem. Ber. 1963, 96, 802. doi: 10.1002/cber.19630960321
21. [21]
  Gao, T.; Zhao, M.; Meng, X.; Li, C.; Chen, B. Synlett 2011, 1281.
22. [22]
  Efimov, I.; Beliaev, N.; Beryozkina, T.; Slepukhin, P.; Bakulev, V. Tetrahedron Lett. 2016, 57, 1949. doi: 10.1016/j.tetlet.2016.03.058
23. [23]
  Zheng, X.; Wan, J.-P. Adv. Synth. Catal. 2019, 361, 5690. doi: 10.1002/adsc.201901054
24. [24]
  Wang, G.; Guo, Y.; Wan, J.-P. Chin. J. Org. Chem. 2020, 40, 645(in Chinese).
25. [25]
  Bae, I.; Han, H.; Chang, S. J. Am. Chem. Soc. 2005, 127, 2038. doi: 10.1021/ja0432968
26. [26]
  Chang, S.; Lee, M.; Jung, D. Y.; Yoo, E. J.; Cho, S. H.; Han, S. K. J. Am. Chem. Soc. 2006, 128, 12366. doi: 10.1021/ja064788i
27. [27]
  Kim, J.; Lee, S. Y.; Lee, J.; Do, Y.; Chang, S. J. Org. Chem. 2008, 73, 9454. doi: 10.1021/jo802014g
28. [28]
  Zhou, Y.; Webber, S. E.; Murphy, D. E.; Li, L.-S.; Dragovich, P. S.; Tran, C. V.; Sun, Z.; Ruebsam, F.; Shah, A. M.; Tsan, M.; Showalter, R. E.; Patel, R.; Li, B.; Zhao, Q.; Han, Q.; Hermann, T.; Kissinger, C. R.; LeBrun, L.; Sergeeva, M. V.; Kirkovsky, L. Bioorg. Med. Chem. Lett. 2008, 18, 1413. doi: 10.1016/j.bmcl.2008.01.007
29. [29]
  Murugavel, G.; Punniyamurthy, T. J. Org. Chem. 2015, 80, 6291. doi: 10.1021/acs.joc.5b00738
30. [30]
  Jagadale, M.; Bhange, P.; Salunkhe, R.; Bhange, D.; Rajmane, M.; Rashinkar, G. Appl. Catal. A: Gen. 2016, 511, 95. doi: 10.1016/j.apcata.2015.11.010
31. [31]
  Kim, M. J.; Kim, B. R.; Lee, C. Y.; Kim, J. Tetrahedron Lett. 2016, 57, 4070. doi: 10.1016/j.tetlet.2016.07.085
32. [32]
  Yavari, I.; Ahmadian, S.; Majid, G.-D.; Solgi, Y. Tetrahedron Lett. 2011, 52, 668. doi: 10.1016/j.tetlet.2010.11.135
33. [33]
  He, X. W.; Shang, Y.; Hu, J.; Ju, K.; Jiang, W.; Wang, S. Sci. China, Chem. 2012, 55, 214. doi: 10.1007/s11426-011-4405-9
34. [34]
  Yao, B.; Shen, C.; Liang, Z.; Zhang, Y. J. Org. Chem. 2014, 79, 936. doi: 10.1021/jo402368x
35. [35]
  (a) Pettit, G. R.; Kadunce, R. E. J. Org. Chem. 1962, 27, 4566.
  (b) Gazvoda, M.; Kočevar, M.; Polance, S. Eur. J. Org. Chem. 2013, 5381.
  (c) Chandna, N.; Chandak, N.; Kumar, P.; Kapoor, J. K.; Sharma, P. K. Green Chem. 2013, 15, 2294.
  (d) Jeong, Y.; Ban, J.; Lim, M.; Rhee, H. Synthesis 2018, 50, 1867.
36. [36]
  Wan, X.; Chen, S.; Xu, Y. Org. Lett. 2011, 13, 6152. doi: 10.1021/ol2024604
37. [37]
  Chen, J.; Long, W.; Fang, S.; Yang, Y.; Wan, X. Chem. Commun. 2017, 53, 13256. doi: 10.1039/C7CC07364J
38. [38]
  Chen, J.; Long, W.; Yang, Y.; Wan, X. Org. Lett. 2018, 20, 2663. doi: 10.1021/acs.orglett.8b00867
39. [39]
  Niu, Z.; Lin, S.; Dong, Z.; Sun, H.; Liang, F.; Zhang, J. Org. Biomol. Chem. 2013, 11, 2460. doi: 10.1039/c3ob27351b
40. [40]
  Wei, Y.; Lin, S.; Liang, F. Org. Lett. 2012, 14, 4202. doi: 10.1021/ol301871s
41. [41]
  Chow, S. Y.; Odell, L. R. J. Org. Chem. 2017, 82, 2515. doi: 10.1021/acs.joc.6b02894
42. [42]
  Friis, S. D.; Lindhardt, A. T.; Skrydstrup, T. Acc. Chem. Res. 2016, 49, 594. doi: 10.1021/acs.accounts.5b00471
43. [43]
  Trillo, P.; Slagbrand, T.; Tinnis, F.; Adolfsson, H. ChemistryOpen 2017, 6, 484. doi: 10.1002/open.201700087
44. [44]
  Yang, W.; Huang, D.; Zeng, X.; Luo, D.; Wang, X.; Hu, Y. Chem. Commun. 2018, 54, 8222. doi: 10.1039/C8CC04699A
45. [45]
  Aswad, M.; Chiba, J.; Tomohiro, T.; Hatanaka, Y. Chem. Commun. 2013, 49, 10242. doi: 10.1039/c3cc46055j
46. [46]
  Khadijeh, H.; Hassan, Z.-B. Synlett 2014, 25, 2044. doi: 10.1055/s-0034-1378376
47. [47]
  Kim, J.; Stahl, S. S. J. Org. Chem. 2015, 80, 2448. doi: 10.1021/jo5029198
48. [48]
  Zheng, Y.; Mao, J. C.; Chen, J.; Rong, G. W.; Liu, D. F.; Yan, H.; Chi, Y. J.; Xu, X. F. RSC Adv. 2015, 5, 50113. doi: 10.1039/C5RA06773A
49. [49]
  Yi, F.; Sun, Q.; Sun, J.; Fu, C.; Yi, W. J. Org. Chem. 2019, 84, 6780. doi: 10.1021/acs.joc.9b00538
50. [50]
  Liu, B.; Ning, Y.; Virelli, M.; Zanoni, G..; Dnderson, E. A.; Bi, X. J. Am. Chem. Soc. 2019, 141, 1593. doi: 10.1021/jacs.8b11039
51. [51]
  Ning, Y.; Ji, Q.; Liao, P.; Anderson, E. A.; Bi, X. Angew. Chem., Int. Ed. 2017, 56, 13805. doi: 10.1002/anie.201705122
52. [52]
  Zhang, Y.; Chen, Z. Tetrahedron Lett. 2018, 59, 4183. doi: 10.1016/j.tetlet.2018.10.027
53. [53]
  Chen, J.; Long, W.; Zhao, Y.; Li, H.; Zheng, Y.; Lian, P.; Wan, X. Chin. J. Chem. 2018, 36, 857. doi: 10.1002/cjoc.201800208
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