Research and Application of N-Ts Cyanamides in Organic Synthesis

  • Chuanchuan Wang ,
  • Zhiwei Ma ,
  • Xuehui Hou ,
  • Longhua Yang ,
  • Yajing Chen
Expand
  • a Faculty of Science, Henan University of Animal Husbandry and Economy, Zhengzhou 450046
    b School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001
These authors contributed equally to this work.
* Corresponding authors. E-mail: ;

Received date: 2022-07-13

  Revised date: 2022-08-08

  Online published: 2022-09-15

Supported by

Natural Science Foundation of Henan Province(212300410152); Henan University of Animal Husbandry and Economy(2019HNUAHEDF011); Henan University of Animal Husbandry and Economy(XKYCXJJ2020006)

Abstract

N-Ts cyanamide, which has been widely used in the construction of nitrogen-containing framework, is one of the efficient and practical multifunctional synthetic precursors in organic synthesis. The progress in application of N-Ts cyanamide according to the reaction types is summarized, including the application in cyanation, cyclization reaction via cyanamide anion, cyanamidation, sulfonylation and cyclization reaction via cyano-group. The future development direction of this field is also prospected.

Cite this article

Chuanchuan Wang , Zhiwei Ma , Xuehui Hou , Longhua Yang , Yajing Chen . Research and Application of N-Ts Cyanamides in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2023 , 43(1) : 74 -93 . DOI: 10.6023/cjoc202207022

References

[1]
Frederick, K. J. J. Chem. Soc. 1949, 1034.
[2]
Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem. Int. Ed. 2011, 50, 519.
[3]
Cui, J.; Song, J.; Liu, Q.; Liu, H.; Dong, Y. Chem. Asian J. 2018, 13, 482.
[4]
Wang, R.; Falck, J. R. Chem. Commun. 2013, 49, 6516.
[5]
Gong, T.-J.; Xiao, B.; Cheng, W.-M.; Su, W.; Xu, J.; Liu, Z.-J.; Liu, L.; Fu, Y. J. Am. Chem. Soc. 2013, 135, 10630.
[6]
Chaitanya, M.; Yadagiri, D.; Anbarasan, P. Org. Lett. 2013, 15, 4960.
[7]
Gu, L.-J.; Jin, C.; Wang, R.; Ding, H.-Y. ChemCatChem 2014, 6, 1225.
[8]
Han, J.; Pan, C.; Jia, X.; Zhu, C. Org. Biomol. Chem. 2014, 12, 8603.
[9]
Dong, J.; Wu, Z.; Liu, Z.; Liu, P.; Sun, P. J. Org. Chem. 2015, 80, 12588.
[10]
Zhu, X.; Shen, X.-J.; Tian, Z.-Y.; Lu, S.; Tian, L.-L.; Liu, W.-B.; Song, B.; Hao, X.-Q. J. Org. Chem. 2017, 82, 6022.
[11]
Zhang, H.; Jing, Li, Zheng, Y.; Sang, R.; Zhao, Y.; Wang, Q.; Wu, Y. Eur. J. Org. Chem. 2018, 723.
[12]
Li, J.; Shi, L.; Zhang, S.-P.; Wang, X.-Y.; Zhu, X.; Hao, X.-Q.; Song, M.-P. J. Org. Chem. 2020, 85, 10835.
[13]
Lv, S.; Li, Y.; Yao, T.; Yu, X.; Zhang, C.; Hai, L.; Wu, Y. Org. Lett. 2018, 20, 4994.
[14]
Jia, J.; Liu, X.; Shi, J.; Xu, H. E.; Yi, W. Asian J. Org. Chem. 2015, 4, 1250.
[15]
Chaitanya, M.; Anbarasan, P. J. Org. Chem. 2015, 80, 3695.
[16]
Deng, C.; Sun, Y.; Ren, Y.; Zhang, W. Dalton Trans. 2019, 48, 168.
[17]
Mishra, N. K.; Jeong, T.; Sharma, S.; Shin, Y.; Han, S.; Park, J.; Oh, J. S.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Adv. Synth. Catal. 2015, 357, 1293.
[18]
Chaitanya, M.; Anbarasan, P. Org. Lett. 2015, 17, 3766-3769.
[19]
Su, W.; Gong, T.-J.; Xiao, B.; Fu, Y. Chem. Commun. 2015, 51, 11848.
[20]
Lu, X.; Huang, Y. Org. Chem. Front. 2021, 8, 3008.
[21]
Li, J.; Xu, W.; Ding, J.; Lee, K.-H. Tetrahedron Lett. 2016, 57, 1205.
[22]
Song, F.; Salter, R.; Chen, L. J. Org. Chem. 2017, 82, 3530.
[23]
Heydari, S.; Habibi, D.; Faraji, A. R.; Keypour, H.; Mahmoudabadi, M. Inorg. Chim. Acta 2021, 514, 119956.
[24]
Yang, Y.; Buchwald, S. L. Angew. Chem. Int. Ed. 2014, 53, 8677.
[25]
Yang, Y.; Liu, P. ACS Catal. 2015, 5, 2944.
[26]
Yang, Y. Angew. Chem. Int. Ed. 2016, 55, 345.
[27]
Zhao, W.; Montgomery, J. Angew. Chem. Int. Ed. 2015, 54, 12683.
[28]
Zhao, W.; Montgomery, J. J. Am. Chem. Soc. 2016, 138, 9763.
[29]
Jia, T.; He, Q.; Ruscoe, R. E.; Pulis, A. P.; Procter, D. J. Angew. Chem. Int. Ed. 2018, 57, 11305.
[30]
Wen, L.; Zhang, H.; Wang, J.; Meng, F. Chem. Commun. 2018, 54, 12832.
[31]
Jia, T.; Smith, M. J.; Pulis, A. P.; Perry, G. J. P.; Procter, D. J. ACS Catal. 2019, 9, 6744.
[32]
Li, Z.; Zhang, L.; Nishiura, M.; Luo, G.; Luo, Y.; Hou, Z. ACS Catal. 2020, 10, 11685.
[33]
Li, J.; Ackermann, L. Angew. Chem. Int. Ed. 2015, 54, 3635.
[34]
Yu, D.-G.; Gensch, T.; Azambuja, F.; Va?squez-Céspedes, S.; Glorius, F. J. Am. Chem. Soc. 2014, 136, 17722.
[35]
Cai, Y.; Qian, X.; Rérat, A.; Auffrant, A.; Gosmini, C. Adv. Synth. Catal. 2015, 357, 3419.
[36]
Liu, W.; Ackermann, L. Chem. Commun. 2014, 50, 1878.
[37]
Mishra, A.; Vats, T. K.; Deb, I. J. Org. Chem. 2016, 81, 6525.
[38]
Li, H.; Chen, J.; Dong, J.; Kong, W. Org. Lett. 2021, 23, 6466.
[39]
Liu, W.; Richter, S. C.; Mei, R.; Feldt, M.; Ackermann, L. Chem. Eur. J. 2016, 22, 17958.
[40]
Yu, X.; Tang, J.; Jin, X.; Yamamoto, Y.; Bao, M. Asian J. Org. Chem. 2018, 7, 550.
[41]
Anbarasan, P.; Neumann, H.; Beller, M. Chem. Eur. J. 2011, 17, 4217.
[42]
Yang, Y.; Zhang, Y.; Wang, J. Org. Lett. 2011, 13, 5608.
[43]
Kiyokawa, K. Nagata, T.; Minakata, S. Angew. Chem. Int. Ed. 2016, 55, 10458.
[44]
Benn, K.; Nicholson, K.; Langer, T.; Thomas, S. P. Chem. Commun. 2021, 57, 9406.
[45]
Kiyokawa, K.; Hata, S.; Kainuma, S.; Minakata, S. Chem. Commun. 2019, 55, 458.
[46]
Zhang, W.; Li, T.; Wang, Q.; Zhao, W. Adv. Synth. Catal. 2019, 361, 4914.
[47]
Ren, X.; Shen, C.; Wang, G.; Shi, Z.; Tian, X.; Dong, K. Org. Lett. 2021, 23, 2527.
[48]
Bhat. S. V.; Robinson, D.; Moses, J. E.; Sharma, P. Org. Lett. 2016, 18, 1100.
[49]
Sharma, P.; Bhat, S. V.; Prabhath, M. R. R.; Molino, A.; Nauha, E.; Wilson, D. J. D.; Moses, J. E. Org. Lett. 2018, 20, 4263.
[50]
Wang, C.-C.; Qu, Y.-L.; Liu, X.-H.; Ma, Z.-W.; Yang, B.; Liu, Z.-J.; Chen, X.-P.; Chen, Y.-J. J. Org. Chem. 2021, 86, 3546.
[51]
Wang, C.-C.; Wang, X.-L.; Zhang, Q.-L.; Liu, J.; Ma, Z.-W.; Liu, Z.-J.; Chen, Y.-J. Org. Chem. Front. 2022, 9, 1574.
[52]
Ayres, J. N.; Ashford, M. W.; St?ckl, Y.; Prudhomme, V.; Ling, K. B.; Platts, J. A.; Morrill, L. C. Org. Lett. 2017, 19, 3835.
[53]
Ayres, J. N.; Williams, M. T. J.; Tizzard, G. J.; Coles, S. J.; Ling, K. B.; Morrill, L. C. Org. Lett. 2018, 20, 5282.
[54]
Li, J.-S.; Yang, P.-P.; Chen, G.-Q.; Xie, X.-Y.; Li, Z.-W.; Li, W.-S.; Liu, W.-D. Asian J. Org. Chem. 2019, 8, 246.
[55]
Kasthuri, M.; Babu, H. S.; Kumar, K. S.; Sudhakar, C.; Kumar, P. V. N. Synlett 2015, 26, 897.
[56]
?lachtová, V.; Chasák, J.; Brulíková, L. ACS Omega 2019, 4, 19314.
[57]
Murthy, V. N.; Nikumbh, S. P.; Kumar, S. P.; Rao, L. V.; Raghunadh, A. Tetrahedron Lett. 2015, 56, 5767.
Outlines

/