Citation: Feng Yadong, Zhang Zhenyue, Qi Fu, Yao Qiuhong, Huang Huabin, Shen Jinhai, Cui Xiuling. Ir-catalyzed regiospecific mono-sulfamidation of arylquinazolinones[J]. Chinese Chemical Letters, ;2020, 31(1): 58-60. doi: 10.1016/j.cclet.2019.05.013 shu

Ir-catalyzed regiospecific mono-sulfamidation of arylquinazolinones

Feng Yadong ^a,b,* ,
Zhang Zhenyue ^b ,
Qi Fu ^a ,
Yao Qiuhong ^a ,
Huang Huabin ^a ,
Shen Jinhai ^a ,
Cui Xiuling ^b,**

a.
College of Environment and Public Health, Xiamen Huaxia University, Xiamen 361024, China
b.
Engineering Research Center of Molecular Medicine of Ministry of Education, Key Laboratory of Fujian Molecular Medicine, Key Laboratory of Xiamen Marine and Gene Drugs, School of Biomedical Sciences, Huaqiao University, Xiamen 361021, China

E-mail addresses:

fengyd@hxxy.edu.cn

cuixl@hqu.edu.cn

Received Date: 26 March 2019
Revised Date: 24 April 2019
Accepted Date: 7 May 2019
Available Online: 7 January 2019

Figures(2)

An Ir-catalyzed selective mono-sulfamidation of 2-arylquinazolinones has been achieved with a low catalyst loading under mild conditions. A series of regioselective mono-sulfamided 2-arylquinazolinones were obtained in up to 90% yields. Compared with our previous work of constructing di-sulfamidated 2-arylquinazolinones, the mono-sulfamided products could be obtained selectively by changing the ratio of substrates, the loading of catalyst, acid additive, and reaction time.
- Ir-catalyzed,
- C-H activation,
- Mono-sulfamidation,
- Selectivity,
- Arylquinazolinones
1. [1]
  (a) A.K. Nanda, S. Ganguli, R. Chakraborty, Molecules 12 (2007) 2413-2426;
  (b) J.H. Chan, J.S. Hong, L.F. Kuyper, et al., J. Med. Chem. 38 (1995) 3608-3616;
  (c) H. Kikuchi, K. Yamamoto, S. Horoiwa, et al., J. Med. Chem. 49 (2006) 4698-4706;
  (d) M.H. Yen, J.R. Sheu, I.H. Peng, Y.M. Lee, J.W.J. Chern, Pharm. Pharmacol. 48 (1996) 90-95;
  (e) A. Archana, V.K. Shrivastava, R. Chandra, A. Kumar, Indian J. Chem. 41B (2002) 2371-2375;
  (f) J. Kunes, J. Bazant, M. Pour, K. Waisser, M. Slosarek, J. Janota, Farmaco. 55 (2000) 725-729;
  (g) K. Waisser, J. Gregor, H. Dostal, et al., Farmaco 56 (2001) 803-807;
  (h) Y. Takase, T. Saeki, N. Watanabe, et al., J. Med. Chem. 37 (1994) 2106-2111;
  (i) M. Dupuy, F. Pinguet, O. Chavignon, et al., Chem. Pharm. Bull. 49 (2001) 1061-1065;
  (j) P.M. Chandrika, T. Yakaiah, A.R.R. Rao, et al., Eur. J. Med. Chem. 43 (2008) 846-852.
2. [2]
  Y. Feng, Y. Li, G. Cheng, L. Wang, X. Cui, J. Org. Chem. 80(2015) 7099-7107. doi: 10.1021/acs.joc.5b00957
3. [3]
  M. Liu, M. Shu, C. Yao, G. Yin, D. Wang, J. Huang, Org. Lett. 18(2016) 824-827. doi: 10.1021/acs.orglett.6b00113
4. [4]
  L. Wei, G. He, X. Kong, et al., J. Org. Chem. 83(2018) 6719-6727. doi: 10.1021/acs.joc.8b00168
5. [5]
  Y. Zhang, Y. Shao, J. Gong, et al., Adv. Synth. Catal. 17(2018) 3260-3265.
6. [6]
  D.N. Garad, A.B. Viveki, S.B. Mhaske, J. Org. Chem. 12(2017) 6366-6372. doi: 10.1021/acs.joc.7b00948
7. [7]
  A.B. Viveki, S.B. Mhaske, J. Org. Chem. 16(2018) 8906-8913. doi: 10.1021/acs.joc.8b01143
8. [8]
  G. Bairy, S. Das, H.M. Begam, R. Jana, Org. Lett. 20(2018) 7107-7112. doi: 10.1021/acs.orglett.8b03048
9. [9]
  Y. Feng, N. Tian, Y. Li, et al., Org. Lett. 19(2017) 1658-1661. doi: 10.1021/acs.orglett.7b00452
10. [10]
  (a) J. Kim, S. Chang, Angew. Chem. Int. Ed. 53 (2014) 2203-2207;
  (b) T. Kang, Y. Kim, D. Lee, Z. Wang, S. Chang, J. Am. Chem. Soc. 136 (2014) 4141-4144;
  (c) H. Hwang, J. Kim, J. Jeong, S. Chang, J. Am. Chem. Soc. 136 (2014) 10770-10776;
  (d) C. Pi, X. Cui, Y. Wu, J. Org. Chem. 80 (2015) 7333-7339;
  (e) B. Zhu, X. Cui, C. Pi, D. Chen, Y. Wu, Adv. Synth. Catal. 358 (2016) 326-332;
  (f) Y. Park, Y. Kim, S. Chang, Chem. Rev. 117 (2017) 9247-9301;
  (g) D. Lee, Y. Kim, S. Chang, J. Org. Chem. 78 (2013) 11102-11109;
  (h) T. Kang, H. Kim, J.G. Kim, S. Chang, Chem. Commun. 50 (2014) 12073-12075;
  (i) H. Kim, G. Park, J. Park, S. Chang, ACS Catal. 6 (2016) 5922-5929.
11. [11]
  J.Y. Kim, S.H. Park, J. Ryu, et al., J. Am. Chem. Soc. 134(2012) 9110-9113. doi: 10.1021/ja303527m
12. [12]
  D.G. Yu, M. Suri, F. Glorius, J. Am. Chem. Soc. 135(2013) 8802-8805. doi: 10.1021/ja4033555
13. [13]
  (a) V.S. Thirunavukkarasu, K. Raghuvanshi, L. Ackermann, Org. Lett. 15 (2013) 3286-3289;
  (b) B. Sun, T. Yoshino, S. Matsunaga, M. Kanai, Adv. Synth. Catal. 356 (2014) 1491-1495;
  (c) N. Wang, R. Li, L. Li, et al., J. Org. Chem. 79 (2014) 5379-5385;
  (d) B. Zhou, Y. Yang, J. Shi, H. Feng, Y. Li, Chem. Eur. J. 19 (2013) 10511-10515;
  (e) M.E. Wei, L.H. Wang, Y.Y. Li, X. Cui, Chin. Chem. Lett. 26 (2015) 1336-1340;
  (f) C. Pan, N. Jin, H. Zhang, J. Han, C. Zhu, J. Org. Chem. 79 (2014) 9427-9432.
14. [14]
  Y. Feng, Y. Li, Y. Yu, L. Wang, X. Cui, RSC Adv. 8(2018) 8450-8454. doi: 10.1039/C8RA00524A
15. [15]
  (a) L. Wang, D. Xiong, L. Jie, C. Yu, X. Cui, Chin. Chem. Lett. 29 (2018) 907-910;
  (b) T. Yuan, C. Pi, C. You, et al., Chem. Commun. 52 (2019) 129-258;
  (c) L. Xu, T. Li, L. Wang, X. Cui, J. Org. Chem. 84 (2019) 560-567;
  (d) Z. Yang, L. Jie, Z. Yao, Z. Yang, X. Cui, Adv. Catal. Synth. 1 (2019) 214-218;
  (e) M. Gao, Y. Li, L. Xie, R. Chauvin, X. Cui, Chem. Commun. 52 (2016) 2846-2849;
  (f) Y. Yu, Y. Feng, R. Chauvin, et al., Org. Lett. 20 (2018) 4209-4212;
  (g) Y. Li, C. Jia, H. Li, et al., Org. Lett. 20 (2018) 4930-4933;
  (h) L. Jie, L. Wang, D. Xiong, et al., J. Org. Chem. 83 (2018) 10974-10984;
  (i) L. Xu, L. Wang, Y. Feng, et al., Org. Lett. 19 (2017) 4343-4346.
16. [16]
  (a) J. Ryu, K. Shin, S.H. Park, J.Y. Kim, S. Chang, Angew. Chem. Int. Ed. 51 (2012) 9904-9908;
  (b) K. Shin, Y. Baek, S. Chang, Angew. Chem. Int. Ed. 52 (2013) 8031-8036;
  (c) J. Ryu, J. Kwak, K. Shin, D. Lee, S. Chang, J. Am. Chem. Soc. 135 (2013) 12861-12868.
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