SIOC English
有机化学
高级检索

有机化学 >

0 202604001

DOI: https://doi.org/10.6023/cjoc202604001

研究论文

四丁基羧酸铵与N-芳基丙烯酰胺的2-吲哚酮电化学合成

  • Gu ,
  • Xiong ,
  • Wang ,
  • Kaimin ,
  • Yuan ,
  • Tengrui ,
  • Gou ,
  • Quan ,
  • Fan ,
  • Baomin
展开
  • a云南民族大学 化学与环境学院 云南省手性功能物质研究与利用重点实验室（筹）, 昆明 650504;
    b长江师范学院 化学化工学院, 重庆 408100

收稿日期: 2026-06-25

  修回日期: 2026-08-04

  网络出版日期: 2026-09-22

基金资助

云南省教育厅科学研究基金项目基金(No. 2025Y0675), 国家自然科学基金(No.22361025)和重庆市自然科学基金(No. CSTB2023NSCQ-MSX0213）资助项目.

收起

Electrochemical synthesis of 2-Indolinone through tetrabutylammonium carboxylate and N-arylacrylamides

  • 顾雄 ,
  • 王凯民 ,
  • 袁藤瑞 ,
  • 苟铨 ,
  • 樊保敏
Expand
  • aSchool of Chemistry and Environment, Yunnan Key Laboratory of Chiral Functional Substance Research and Application, Yunnan Minzu University, Kunming 650504, China;
    bSchool of Chemistry and chemical engineering, Yangtze Normal University, Chongqing 408100, China

Received date: 2026-06-25

  Revised date: 2026-08-04

  Online published: 2026-09-22

Supported by

Yunnan Provincial Department of Education Science Research Fund Project (No. 2025Y0675), National Natural Science Foundation of China (No.22361025) and Natural Science Foundation of Chongqing (No. CSTB2023NSCQ-MSX0213).

Fold

摘要

报道了一种电化学条件下的2-吲哚酮类化合物的合成方法. 该方法以N-芳基丙烯酰胺作为底物,利用四丁基羧酸铵作为烷基化试剂和电解质,其通过阳极氧化脱羧生成烷基自由基,随后经过自由基环化合成一系列2-吲哚酮类衍生物. 相对于传统的烷基化反应,该反应条件温和,操作简单,具有良好的官能团耐受性,不需要添加额外的氧化剂和催化剂,对环境友好.

关键词： 电化学; N-芳基丙烯酰胺; 四丁基羧酸铵; 烷基化; 2-吲哚酮

本文引用格式

Gu , Xiong , Wang , Kaimin , Yuan , Tengrui , Gou , Quan , Fan , Baomin . 四丁基羧酸铵与N-芳基丙烯酰胺的2-吲哚酮电化学合成[J]. 有机化学, 0 : 202604001 . DOI: 10.6023/cjoc202604001

Abstract

An efficient electrochemical synthesis of 2-Indolinone is reported in this paper. This method uses N-arylacrylamides as the starting material, employing commercially available tetrabutylammonium carboxylate as the alkylating agent and electrolyte, which generates the alkyl radical through anodic oxidative decarboxylation, and then affords a series of 2-Indolinone derivatives via radical cyclization. Compared with traditional approaches, this approach has the advantages of simple operation, mild reaction conditions and wide range of substrates, environmentally friendly, no extra oxidants or catalysts.

Key words： Electrochemistry; N-arylacrylamides; Tetrabutylammonium carboxylate; Alkylation; 2-Indolinone

参考文献

[1] Guo B.-B.; M W.; Xu K.; Zeng, C.-C. Chin. J. Org. Chem.2021, 41, 2621-2635 (in Chinese).
(孟薇,徐坤,郭兵兵,曾程初,有机化学,2021,41,2621-2635.)
[2] Lu L.-Y.; Qiu, X.-D. Chin. J. Org. Chem.2024, 44, 1701-1718 (in Chinese).
(陆玲依,邱晓东,有机化学,2024,44,1701-1718)
[3] Mandal D.; Roychowdhury S.; Biswas J. P.; Maiti S.; Maiti, D. Chem. Soc. Rev.2022, 51, 7358-7426.
[4] Dong Z.; Ren Z.; Thompson S. J.; Xu Y.; Dong G.-B. Chem. Rev.2017, 117, 9333-9403.
[5] Lipinski C. A.; Lombardo F.; Dominy B. W.; Feeney, P. J. Adv. Drug Deliv. Rev.2001, 46, 3-26.
[6] Mooney R.; Masala M.; Martial T.; McGinness C.; Henriquez F. L.; Williams, R. A. M. Sci. Rep.2020, 10, 6420.
[7] Leeson P. D.; Springthorpe, B. Nat. Rev. Drug Discov.2007, 6, 881-890.
[8] Marti C.; Carreira, E. M. Eur. J. Org. Chem.2003, 2003, 2209-2219.
[9] Galliford C. V.; Scheidt, K. A. Angew. Chem. Int. Ed.2007, 46, 8748-8758.
[10] Singh G. S.; Desta, Z. Y. Chem. Rev.2012, 112, 6104-6155.
[11] Tan Y.-B.; Shu, H.-B; Huang H.-W.Chin. J. Org. Chem. 2025, 45, 2086-2108 (in Chinese).
(谭永波,舒洪波,黄华文,有机化学,2025,45,2086-2108.)
[12] Figueiredo G. S.; Zardo R. S.; Silva B. V.; Violante F. A.; Pinto A. C.; Fernandes, P. D. Pharmacol., Biochem. Behav.2013, 103, 431-439.
[13] Kamano Y.; Zhang H.-P.; Ichihara Y.; Kizu H.; Komiyama K.; Pettit, G. R. Tetrahedron Lett.1995, 36, 2783-2784.
[14] Bagal S. K.; Brown A. D.; Cox P. J.; Omoto K.; Owen R. M.; Pryde D. C.; Sidders B.; Skerratt S. E.; Stevens E. B.; Storer R. I.; Swain, N. A. J. Med. Chem.2013, 56, 593-624.
[15] Lv M.-J.; Li X.-X. ACS Catal.2021, 11, 14829-14835.
[16] Hou Y.; Huo J.-Y.; Li R.-X.; Hou J.; Lei P.; Wei H.-B.; Xie W.-Q. Org. Lett.2023, 25, 6949-6953.
[17] Wu Z.-L.; Luo W.; Ding R.; Xin C.; Wang C.-Y.; He, W.-M. Chin. J. Org. Chem.2025, 45, 3691-3700 (in Chinese).
(伍智林,罗伟,丁柔,辛翠,王从洋,何卫民,有机化学,2025,45,3691-3700.)
[18] Marchese A. D.; Larin E. M.; Mirabi B.; Lautens, M. Acc. Chem. Res.2020, 53, 1605-1619.
[19] Zhang Y.-Y.; Yan H.-B.; Zhu X.-J.; Shi Y.-J.; Li J.-X.; Yang D.-S.; Li, X.-F. Chin. J. Org. Chem.2026, 46, 653-663 (in Chinese).
(张云一,严含冰,朱先进,石永佳,李俊鑫,杨道山,李旭锋,有机化学,2026,46,653-663.)
[20] Matcha K.; Narayan R.; Antonchick A. P.Angew. Chem. Int. Ed. 2013, 52, 7985-7989.
[21] Zhang M.-Z.; Yang X.; Yin J.-X.; Deng Y.; Tan H.-Y.; Bai Y.-H.; Li Y.-L.; Wen J.-W.; Chen T.-Q. Org. Lett.2024, 26, 3923-3928.
[22] Hou H.; Ou W.; Su, C.-L. J. Org. Chem.2024, 89, 4120-4127.
[23] Sui D.-D.; Cen N.-N.; Gong R.-Q.; Chen Y.; Chen, W.-B. Chin. J. Org. Chem.2023, 43, 3239-3245 (in Chinese).
(岁丹丹,岑南楠,龚若蕖,陈阳,陈文博,有机化学,2023,43,3239-3245.)
[24] Xie Z.-G.; Li P.-H.; Hu Y.; Xu N.; Wang, L. Org. Biomol. Chem.2017, 15, 4205-4211.
[25] Qiu Z.-H.; Zheng W.-H.; Dai Y.-X.; Dong B.-C.; Cao T.; Jin H.-M.Chem. Commun. 2026, 62, 1959-1962.
[26] Biswas P.; Paul S.; Guin, J. Angew. Chem. Int. Ed.2016, 55, 7756-7760.
[27] Pan C.-D.; Fu Y.; Ni Q.-T.; Yu, J.-T. J. Org. Chem.2017, 82, 5005-5010.
[28] Zhang L.; Zhou H.-F.; Bai S.-K.; Li S.-D. Dalton Trans.2021, 50, 3201-3206.
[29] Xu X.-S.; Li X.-Q.; Chen H.-M.; Sun Z.T.; Yang H.; Mao F.-H.; Yan X.-H. Synlett.2022, 34, 63-66.
[30] Yang P.-Y.; Wang L.-L.; Yan M.; Yuan J.-W.; Xiao Y.-M.; Yang L.-R.; Xu X.-J.; Qu, L.-B. Org. Biomol. Chem.2025, 23, 1653-1661.
[31] Dai Q.; Yu J.-T.; Jiang Y.; Guo S.-J.; Yang H.-T.; Cheng J. Chem. Commun.2014, 50, 3865-3867
[32] Ding S.-Y.; Ren H.-P.; Zhu M.; Ma Q.; Miao Z.-C.; Li P.-F. Synth. Commun.2020, 51, 593-600.
[33] Jha A. K.; Nair D. P.; Arif M.; Yedase G. S.; Kuniyil R.; Yatham, V. R. J. Org. Chem.2023, 88, 15389-15394.
[34] Zhang S.-X.; Li Y.-F.; Wang T.; Li M.; Wen L.-R.; Guo W.-S. Org. Lett.2022, 24, 1742-1746.
[35] Wang X.-Y.; Zhong Y.-F.; Mo Z.-Y.; Wu S.-H.; Xu Y.-L.; Tang H.-T.; Pan, Y.-M. Adv. Synth. Catal.2020, 363, 208-214.
[36] Ruan Z.-X.; Huang Z.-X.; Xu Z.-N.; Mo, G.-Q; Tian X.; Yu X.-Y.; Ackermann L. Org. Lett.2019, 21, 1237-1240.
[37] Wang Y.; Wang Y.; Wang S.; Yu Z.; Wang S.-Q.; Chen, W.-B. J. Org. Chem.2024, 89, 11950-11958.
[38] Wang D.; Wan Z.-H.; Zhang H.; Alhumade H.; Yi H.; Lei A.-W. ChemSusChem.2021, 14, 5399-5404.
[39] Zhou, Z.-L; Yuan Y.; Cao, Y.-M; Qiao J.; Yao, A.-J; Zhao J.; Zuo, W.-Q; Chen, W.-J; Lei, A.-W. Chin. J. Chem.2019, 37, 611-615.
[40] Heard D. M.; Lennox, A. J. J. Angew. Chem. Int. Ed.2020, 59, 18866-18884.
[41] Fleischmann M.; Pletcher, D. R. Inst. Chem. Rev.1969, 2.
[42] Yan M.; Kawamata Y.; Baran, P. S. Chem. Rev.2017, 117, 13230-13319.
[43] Zhu C.-J.; Ang N. W. J.; Meyer T. H.; Qiu Y.-A.; Ackermann, L. ACS Cent. Sci.2021, 7, 415-431.
[44] Zhou H.-Y.; Tang H.-T.; He, W.-M. Chin. J. Catal.2023, 46, 4-10.
[45] Wu Y.-X.; Xi Y.-C.; Zhao M.; Wang, S.-Y. Chin. J. Org. Chem.2018, 38, 2590-2605 (in Chinese).
(吴亚星,席亚超,赵明,王思懿,有机化学,2018,38,2590-2605.)
[46] Hou Z.-S.; Zhou Q.-Q.; Ye M.; Ma W.-B.; Li D.-F.; Ding B.-J.; Chen M.-Y.; Gong X.-Q.;Yao, Y.-F. Chem. - Eur. J.2019, 25, 4206-4217.
[47] Lu M.-Q.; Xie E.-Q.; Song W.-J.; Wu T.; Cai H. Org. Lett.2026, 28, 3155-3160.
[48] Lu M.-Q.; Chen K.-L.; Wu T.; Cai, H. Angew. Chem. Int. Ed.2025, 64.
[49] Ayitou A. J.-L.; Sivaguru J. Chem. Commun.2011, 47, 2568-2570.
[50] Wu T.; Mu X.; Liu, G.-S. Angew. Chem. Int. Ed.2011, 50, 12578-12581.
[51] Zhao Y.-P.; Sharma N.; Sharma U. K.; Li Z.-H.; Song G.-H.; Van der Eycken, E. V. Chem. -Eur. J.2016, 22, 5878-5882.
Options
文章导航

/

〈 〉