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.
1. [1]
  Wei-Bin Li , Xiao-Chao Huang , Pei Liu , Jie Kong , Guo-Ping Yang . Recent advances in directing group assisted transition metal catalyzed para-selective C-H functionalization. Chinese Chemical Letters, 2025, 36(6): 110543-. doi: 10.1016/j.cclet.2024.110543
2. [2]
  Yajun Gao , Xinyu Yang , Jian Su , Zhizhong Li . A stable scandium(III) metal-organic framework with introduced nitrate ions for enhancing C₂H₆/C₂H₄ selectivity in the separation of MTO products. Chinese Journal of Structural Chemistry, 2025, 44(6): 100576-100576. doi: 10.1016/j.cjsc.2025.100576
3. [3]
  Xiao Tang , Erik V. Van der Eycken , Liangliang Song . Transition metal-catalyzed C-H activation/annulation for the construction of unnatural amino acids and peptides. Chinese Chemical Letters, 2026, 37(2): 111678-. doi: 10.1016/j.cclet.2025.111678
4. [4]
  Shen Wang , Yi Wei , Weijie Li , Chao Han . Advances in copper-based catalysts for selective CO₂ electroreduction to C1 and C2 products. Chinese Journal of Structural Chemistry, 2026, 45(8): 100944-100944. doi: 10.1016/j.cjsc.2026.100944
5. [5]
  Yan Zhao , Zhenming Tian , Qisen Jia , Ting Yao , Jiashu Li , Yanan Wang , Xuejing Cui , Jing Liu , Xin Chen , Luhua Jiang . Crystal orientation dependent charge transfer dynamics and interfacial water configuration boosting photoelectrocatalytic water oxidation to H2O2. Chinese Journal of Structural Chemistry, 2025, 44(7): 100619-100619. doi: 10.1016/j.cjsc.2025.100619
6. [6]
  Chao Chen , Wenwen Yu , Guangen Huang , Xuelian Ren , Xiangli Chen , Yixin Li , Shenggui Liang , Mengmeng Xu , Mingyue Zheng , Yaxi Yang , He Huang , Wei Tang , Bing Zhou . Asymmetric macrocyclization enabled by Rh(Ⅲ)-catalyzed CH activation: Enantioenriched macrocyclic inhibitor of Zika virus infection. Chinese Chemical Letters, 2024, 35(11): 109574-. doi: 10.1016/j.cclet.2024.109574
7. [7]
  Yongli Zhao , Dingsheng Cao , Jie-Ping Wan , Yunyun Liu . Synthesis of 3-phosphinyl chromones via in situ iodination mediated C-H phosphination and the tunable synthesis of 2-phosphoryl chromanones. Chinese Chemical Letters, 2026, 37(1): 111740-. doi: 10.1016/j.cclet.2025.111740
8. [8]
  Lijuan Huang , Rui Gan , Xin Han , Meilin Sun , Li Chen , Wen Liu , Xiaoxin Zhang , Fei Pan . Peroxymonosulfate activation by Fe(Ⅲ)-phytate co-precipitation for efficient water treatment at circumneutral pH: The critical role of direct electron transfer. Chinese Chemical Letters, 2026, 37(5): 111840-. doi: 10.1016/j.cclet.2025.111840
9. [9]
  Caixia Zhu , Qing Hong , Kaiyuan Wang , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Single nanozyme-based colorimetric biosensor for dopamine with enhanced selectivity via reactivity of oxidation intermediates. Chinese Chemical Letters, 2024, 35(10): 109560-. doi: 10.1016/j.cclet.2024.109560
10. [10]
  Congyan Liu , Xueyao Zhou , Fei Ye , Bin Jiang , Bo Liu . Confined electric field in nano-sized channels of ionic porous framework towards unique adsorption selectivity. Chinese Chemical Letters, 2025, 36(2): 109969-. doi: 10.1016/j.cclet.2024.109969
11. [11]
  Zimo Yang , Yan Tong , Yongbo Liu , Qianlong Liu , Zhihao Ni , Yuna He , Yu Rao . Developing selective PI3K degraders to modulate both kinase and non-kinase functions. Chinese Chemical Letters, 2024, 35(11): 109577-. doi: 10.1016/j.cclet.2024.109577
12. [12]
  Hao Li , Yu-Xuan Zhao , Jin-Bo Niu , Jian Song , Sai-Yang Zhang . Hydrazide-based HDAC inhibitors and PROTAC degraders in drug discovery: Recent developments and therapeutic applications. Chinese Chemical Letters, 2026, 37(11): 112263-. doi: 10.1016/j.cclet.2025.112263
13. [13]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
14. [14]
  Junyi Yu , Yin Cheng , Anhong Cai , Xianfeng Huang , Qingrui Zhang . Synthetic Cu(Ⅲ) from copper plating wastewater for onsite decomplexation of Cu(Ⅱ)- and Ni(Ⅱ)-organic complexes. Chinese Chemical Letters, 2025, 36(2): 110549-. doi: 10.1016/j.cclet.2024.110549
15. [15]
  Weidan Meng , Yanbo Zhou , Yi Zhou . Green innovation unleashed: Harnessing tungsten-based nanomaterials for catalyzing solar-driven carbon dioxide conversion. Chinese Chemical Letters, 2025, 36(2): 109961-. doi: 10.1016/j.cclet.2024.109961
16. [16]
  Ying Wang , Hong Yang , Caixia Zhu , Qing Hong , Xuwen Cao , Kaiyuan Wang , Yuan Xu , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Cascading oxidoreductases-like nanozymes for high selective and sensitive fluorescent detection of ascorbic acid. Chinese Chemical Letters, 2025, 36(4): 110153-. doi: 10.1016/j.cclet.2024.110153
17. [17]
  Bo Li , Yuanzhe Cheng , Xuyang Ma , Dongxu Zhao , Yang Zhang , Yongxing Sun , Jia Chen , Li Wu , Liang Zhao , Hongdeng Qiu , Yujian He . Facile and scale-up synthesis of cyano-functionalized covalent organic frameworks for selective gold recovery. Chinese Chemical Letters, 2026, 37(1): 111134-. doi: 10.1016/j.cclet.2025.111134
18. [18]
  Yan-Fang Wang , Jia Liu , Wei Li , Song-Meng Wang , Jian Qin , Cheng-Da Zhao , Liu-Pan Yang , Li-Li Wang . Hybridtube with endo-functionalized cavity for highly selective recognition: Subtle structure changes in guest lead to significant binding affinity variations. Chinese Chemical Letters, 2026, 37(6): 112368-. doi: 10.1016/j.cclet.2026.112368
19. [19]
  Taiwen Chen , Baohua Wang , Lu Zhang , Wenbo Bi , Cong Lyu . Amine/imine-functionalized covalent organic frameworks with high selective capacity of perfluoroalkyl substances: Mechanism and potential application as anode in capacitive deionization. Chinese Chemical Letters, 2026, 37(7): 112297-. doi: 10.1016/j.cclet.2025.112297
20. [20]
  Junhua Li , Yu Fu , Yian Shi . A rapid access to fused polycyclic indolo[2,1-a]isoquinolins via Pd-catalyzed sequential Heck/C-H activation/amination reaction with diaziridinone. Chinese Chemical Letters, 2026, 37(3): 111376-. doi: 10.1016/j.cclet.2025.111376

Get Citation

PDF

XML

Metrics

PDF Downloads(11)
Abstract views(2250)
HTML views(135)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142