Citation: Changwei Chen, Hongyu Zhang, Gang Xu, Sunliang Cui. Oxoarylation of ynamides with N-aryl hydroxamic acids[J]. Chinese Chemical Letters, ;2021, 32(8): 2551-2554. doi: 10.1016/j.cclet.2021.02.054 shu

Oxoarylation of ynamides with N-aryl hydroxamic acids

Changwei Chen ^b ,
Hongyu Zhang ^a ,
Gang Xu ^{a, *,} ,
Sunliang Cui ^b

a.
College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China
b.
College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China

xugang_1030@zju.edu.cn

Received Date: 30 November 2020
Revised Date: 19 February 2021
Accepted Date: 22 February 2021
Available Online: 26 February 2021

Figures(5)

Ynamides are electron-rich alkynes with unique reactivities and act as flexible building blocks in organic synthesis. Therefore, the investigation for transformation of ynamides with exceptional selectivity and efficiency is attractive and interesting. Herein, we report an oxoarylation of ynamides with N-aryl hydroxamic acids. In the presence of catalytic Cu(OTf)₂, both the terminal and internal ynamides could undergo an addition/[3,3] sigmatropic rearrangement cascade with N-aryl hydroxamic acids to achieve oxoarylation, along with providing selective entry to (ortho-amino)arylacetamides and oxindoles. Moreover, deuterium-labelling reaction and gram-scale reaction were conducted to probe the mechanism and showcase the scalability.
- Ynamide,
- Hydroxamic acid,
- Oxoarylation,
- Oxindole,
- Rearrangement
1. [1]
  (a) C.A. Zificsak, J.A. Mulder, R.P. Hsung, C. Rameshkumar, L.L. Wei, Tetrahedron 57 (2001) 7575-7606;
  (b) X.N. Wang, H.S. Yeom, L.C. Fang, et al., Acc. Chem. Res. 47 (2014) 560-578;
  (c) F. Pan, C. Shu, L.W. Ye, Org. Biomol. Chem. 14 (2016) 9456-9465;
  (d) G. Evano, N. Blanchard, G. Compain, et al., Chem. Lett. 45 (2016) 574-585.
2. [2]
  (a) R. Pirwerdjan, P. Becker, C. Bolm, Org. Lett. 18 (2016) 3307-3309;
  (b) F.L. Hong, Z.S. Wang, D.D. Wei, et al., J. Am. Chem. Soc. 141 (2019) 16961-16970;
  (c) Y. Xu, Q. Sun, T.D. Tan, et al., Angew. Chem. Int. Ed. 58 (2019) 16252-16259;
  (d) Z. Zeng, H. Jin, M. Rudolph, et al., Angew. Chem. Int. Ed. 57 (2018) 16549-16553;
  (e) Q. Zhao, D.F.L. Rayo, D. Campeau, et al., Angew. Chem. Int. Ed. 57 (2018) 13603-13607;
  (f) Y. Wang, L.J. Song, X. Zhang, J. Sun, Angew. Chem. Int. Ed. 55 (2016) 9704-9708;
  (g) S.N. Karad, R.S. Liu, Angew. Chem. Int. Ed. 53 (2014) 9072-9076;
  (h) C. Theunissen, B. Métayer, N. Henry, et al., J. Am. Chem. Soc. 136 (2014) 12528-12531;
  (i) M. Lecomte, G. Evano, Angew. Chem. Int. Ed. 55 (2016) 4547-4551;
  (j) D.V. Patil, S.W. Kim, Q.H. Nguyen, et al., Angew. Chem. Int. Ed. 56 (2017) 3670-3674;
  (k) P. Thilmany, G. Evano, Angew. Chem. Int. Ed. 59 (2020) 242-246;
  (l) X. Zeng, J. Li, C.K. Ng, et al., Angew. Chem. Int. Ed. 57 (2018) 2924-2928.
3. [3]
  (a) D. Vasu, H.H. Hung, S. Bhunia, et al., Angew. Chem. Int. Ed. 50 (2011) 6911-6914;
  (b) L. Li, B. Zhou, Y.H. Wang, et al., Angew. Chem. Int. Ed. 54 (2015) 8245-8249.
4. [4]
  (a) S. Xu, J. Liu, D. Hu, X. Bi, Green Chem. 17 (2015) 184-187;
  (b) D.L. Smith, W.R.F. Goundry, H.W. Lam, Chem. Commun. 48 (2012) 1505-1507;
  (c) H. Liu, Y. Yang, J. Wu, et al., Chem. Commun. 52 (2016) 6801-6804.
5. [5]
  (a) L. Hu, S. Xu, Z. Zhao, et al., J. Am. Chem. Soc. 138 (2016) 13135-13138;
  (b) M. Yang, X. Wang, J. Zhao, ACS Catal. 10 (2020) 5230-5235.
6. [6]
  (a) B. Zhou, L. Li, X.Q. Zhu, et al., Angew. Chem. Int. Ed. 56 (2017) 4015-4019;
  (b) B. Zhou, Y.Q. Zhang, K. Zhang, et al., Nat. Commun. 10 (2019) 3234-3244.
7. [7]
  B.S. Bhunia, C.J. Chang, R.S. Liu, Org. Lett. 14(2012) 5522-5525.
8. [8]
  A. Mukherjee, R.B. Dateer, R. Chaudhuri, et al., J. Am. Chem. Soc. 133(2011) 15372-15375. doi: 10.1021/ja208150d
9. [9]
  (a) M.J. Miller, Chem. Rev. 89 (1989) 1563-1579;
  (b) J.B. Neilands, J. Biol. Chem. 270 (1995) 26723-26726;
  (c) R.C. Hider, X. Kong, Nat. Prod. Rep. 27 (2010) 637-657.
10. [10]
  (a) E. Nuti, D. Cuffaro, E. Bernardini, et al., J. Med. Chem. 61 (2018) 4421-4435;
  (b) C. Rouanet-Mehouas, B. Czarny, F. Beau, et al., J. Med. Chem. 60 (2017) 403-414.
11. [11]
  (a) H.Y. Wang, L.L. Anderson, Org. Lett. 15 (2013) 3362-3365;
  (b) J. Wen, A. Wu, P. Chen, et al., Tetrahedron Lett. 56 (2015) 5282-5286.
12. [12]
  (a) C. Beshara, A. Hall, R. Jenkins, et al., Org. Lett. 7 (2005) 5729-5732;
  (b) A. Porzelle, M. Woodrow, N. Tomkinson, Eur. J. Org. Chem. 2008 (2008) 5135-5143;
  (c) A. Porzelle, M. Woodrow, N. Tomkinson, Org. Lett. 12 (2010) 812-815;
  (d) A. Porzelle, M. Woodrow, N. Tomkinson, Org. Lett. 12 (2010) 1492-1495.
13. [13]
  S. Shaaban, V. Tona, B. Peng, N. Maulide, Angew. Chem. Int. Ed. 56(2017) 10938-10941. doi: 10.1002/ange.201703667
14. [14]
  (a) B. Huang, L. Zeng, Y. Shen, S. Cui, Angew. Chem. Int. Ed. 56 (2017) 4565-4568;
  (b) Y. Shen, B. Huang, L. Zeng, S. Cui, Org. Lett. 19 (2017) 4616-4619;
  (c) R. Chen, Y. Liu, S. Cui, Chem. Commun. 54 (2018) 11753-11756;
  (d) L. Zeng, H. Sajiki, S. Cui, Org. Lett. 21 (2019) 6423-6426;
  (e) C. Chen, S. Cui, J. Org. Chem. 84 (2019) 12157-12164;
  (f) L. Zeng, Z. Lai, C. Zhang, et al., Org. Lett. 22 (2020) 2220-2224;
  (g) R. Chen, L. Zeng, B. Huang, et al., Org. Lett. 20 (2018) 3377-3380;
  (h) Y. Shen, C. Wang, W. Chen, et al., Org. Chem. Front. 5 (2018) 3574-3578.
15. [15]
  (a) A.B. Dounay, L.E. Overman, Chem. Rev. 103 (2003) 2945-2964;
  (b) J.J. Badillo, N.V. Hanhan, A.K. Franz, Curr. Opin. Drug Disc. 13 (2010) 758-776;
  (c) R. Dalpozzo, G. Bartoli, G. Bencivenni, Chem. Soc. Rev. 41 (2012) 7247-7290;
  (d) P. Fu, F. Kong, X. Li, et al., Org. Lett. 16 (2014) 3708-3711;
  (e) J. Zhang, Z. Qian, X. Wu, et al., Org. Lett. 16 (2014) 2752-2755.
16. [16]
  (a) M. Chen, X. Wang, P. Yang, et al., Angew. Chem. Int. Ed. 59 (2020) 12199-12205;
  (b) W. Kong, Q. Wang, J. Zhu, J. Am. Chem. Soc. 137 (2015) 16028-16031;
  (c) L. Yin, M. Kanai, M. Shibasaki, Angew. Chem. Int. Ed. 50 (2011) 7620-7623;
  (d) J. Wang, Y. Yuan, R. Xiong, et al., Org. Lett. 14 (2012) 2210-2213;
  (e) M. Ratushnyy, N. Kvasovs, S. Sarkar, et al., Angew. Chem. Int. Ed. 59 (2020) 10316-10320;
  (f) P. Fan, Y. Lan, C. Zhang, et al., J. Am. Chem. Soc. 142 (2020) 2180-2186;
  (g) X. Bai, C. Wu, S. Ge, Y. Lu, Angew. Chem. Int. Ed. 59 (2020) 2764-2768;
  (h) J. Zhu, L. Huang, W. Dong, et al., Angew. Chem. Int. Ed. 58 (2019) 16119-16123;
  (i) Z.J. Zhang, L. Zhang, R.L. Geng, et al., Angew. Chem. Int. Ed. 58 (2019) 12190-12194.
1. [1]
  Wenling Yuan , Fengli Li , Zhe Chen , Qiaoxin Xu , Zhenhua Guan , Nanyu Yao , Zhengxi Hu , Junjun Liu , Yuan Zhou , Ying Ye , Yonghui Zhang . AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement. Chinese Chemical Letters, 2024, 35(5): 108788-. doi: 10.1016/j.cclet.2023.108788
2. [2]
  Yuting Zhang , Zhiqian Wang . Methods and Case Studies for In-Depth Learning of the Aldol Reaction Based on Its Reversible Nature. University Chemistry, 2024, 39(7): 377-380. doi: 10.3866/PKU.DXHX202311037
3. [3]
  Ying-Di Hao , Zhi-Qian Lin , Xiao-Yu Guo , Jiao Liang , Can-Kun Luo , Qian-Tao Wang , Li Guo , Yong Wu . Rhodium-catalyzed Doyle-Kirmse rearrangement reactions of sulfoxoniun ylides. Chinese Chemical Letters, 2024, 35(4): 108834-. doi: 10.1016/j.cclet.2023.108834
4. [4]
  Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
5. [5]
  Ruru Li , Qian Liu , Hui Li , Fengbin Sun , Zhurui Shen . Rational design of dual sites induced local electron rearrangement for enhanced photocatalytic oxygen activation. Chinese Chemical Letters, 2024, 35(11): 109679-. doi: 10.1016/j.cclet.2024.109679
6. [6]
  Huashan Huang , Jingze Chen , Luyun Zhang , Hong Yan , Siqi Li , Fen-Er Chen . Oscillatory flow reactor facilitates fast photochemical Wolff rearrangement toward synthesis of α-substituted amides in flow. Chinese Chemical Letters, 2025, 36(2): 109992-. doi: 10.1016/j.cclet.2024.109992
7. [7]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
8. [8]
  Huipeng Zhao , Xiaoqiang Du . Polyoxometalates as the redox anolyte for efficient conversion of biomass to formic acid. Chinese Journal of Structural Chemistry, 2024, 43(2): 100246-100246. doi: 10.1016/j.cjsc.2024.100246
9. [9]
  Dan-Ying Xing , Xiao-Dan Zhao , Chuan-Shu He , Bo Lai . Kinetic study and DFT calculation on the tetracycline abatement by peracetic acid. Chinese Chemical Letters, 2024, 35(9): 109436-. doi: 10.1016/j.cclet.2023.109436
10. [10]
  Lihang Wang , Mary Li Javier , Chunshan Luo , Tingsheng Lu , Shudan Yao , Bing Qiu , Yun Wang , Yunfeng Lin . Research advances of tetrahedral framework nucleic acid-based systems in biomedicine. Chinese Chemical Letters, 2024, 35(11): 109591-. doi: 10.1016/j.cclet.2024.109591
11. [11]
  Hanqing Zhang , Xiaoxia Wang , Chen Chen , Xianfeng Yang , Chungli Dong , Yucheng Huang , Xiaoliang Zhao , Dongjiang Yang . Selective CO2-to-formic acid electrochemical conversion by modulating electronic environment of copper phthalocyanine with defective graphene. Chinese Journal of Structural Chemistry, 2023, 42(10): 100089-100089. doi: 10.1016/j.cjsc.2023.100089
12. [12]
  Linshan Peng , Qihang Peng , Tianxiang Jin , Zhirong Liu , Yong Qian . Highly efficient capture of thorium ion by citric acid-modified chitosan gels from aqueous solution. Chinese Chemical Letters, 2024, 35(5): 108891-. doi: 10.1016/j.cclet.2023.108891
13. [13]
  Yingying Yan , Wanhe Jia , Rui Cai , Chun Liu . An AIPE-active fluorinated cationic Pt(Ⅱ) complex for efficient detection of picric acid in aqueous media. Chinese Chemical Letters, 2024, 35(5): 108819-. doi: 10.1016/j.cclet.2023.108819
14. [14]
  Fengyun Li , Zerong Pei , Shuting Chen , Gen li , Mengyang Liu , Liqin Ding , Jingbo Liu , Feng Qiu . Multifunctional nano-herb based on tumor microenvironment for enhanced tumor therapy of gambogic acid. Chinese Chemical Letters, 2024, 35(5): 108752-. doi: 10.1016/j.cclet.2023.108752
15. [15]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
16. [16]
  Peizhe Li , Qiaoling Liu , Mengyu Pei , Yuci Gan , Yan Gong , Chuchen Gong , Pei Wang , Mingsong Wang , Xiansong Wang , Da-Peng Yang , Bo Liang , Guangyu Ji . Chlorogenic acid supported strontium polyphenol networks ensemble microneedle patch to promote diabetic wound healing. Chinese Chemical Letters, 2024, 35(8): 109457-. doi: 10.1016/j.cclet.2023.109457
17. [17]
  Yuanjiao Liu , Xiaoyang Zhao , Songyao Zhang , Yi Wang , Yutuo Zheng , Xinrui Miao , Wenli Deng . Site-selection and recognition of aromatic carboxylic acid in response to coronene and pyridine derivative. Chinese Chemical Letters, 2024, 35(8): 109404-. doi: 10.1016/j.cclet.2023.109404
18. [18]
  Shiyu Pan , Bo Cao , Deling Yuan , Tifeng Jiao , Qingrui Zhang , Shoufeng Tang . Complexes of cupric ion and tartaric acid enhanced calcium peroxide Fenton-like reaction for metronidazole degradation. Chinese Chemical Letters, 2024, 35(7): 109185-. doi: 10.1016/j.cclet.2023.109185
19. [19]
  Xubin Qian , Lei Xu , Xu Ge , Zhun Liu , Cheng Fang , Jianbing Wang , Junfeng Niu . Can perfluorooctanoic acid be effectively degraded using β-PbO₂ reactive electrochemical membrane?. Chinese Chemical Letters, 2024, 35(7): 109218-. doi: 10.1016/j.cclet.2023.109218
20. [20]
  Xinyue Lan , Junguang Liang , Churan Wen , Xiaolong Quan , Huimin Lin , Qinqin Xu , Peixian Chen , Guangyu Yao , Dan Zhou , Meng Yu . Photo-manipulated polyunsaturated fatty acid-doped liposomal hydrogel for flexible photoimmunotherapy. Chinese Chemical Letters, 2024, 35(4): 108616-. doi: 10.1016/j.cclet.2023.108616

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(402)
HTML views(5)

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