SIOC English
有机化学
高级检索

有机化学 >

0 202509023 - 202509023

DOI: https://doi.org/10.6023/cjoc202509023

研究论文

锰促进活化烯烃与亚磷酸酯串联磷酰化/环化反应合成γ-咔啉酮衍生物

  • 印丘梅 ,
  • 刘佳乐 ,
  • 邓世强 ,
  • 黄嘉明 ,
  • 蒋洁 ,
  • 唐裕才
展开
  • a湖南文理学院化学与材料工程学院, 电镀废水回用技术湖南省工程研究中心 常德 415000

收稿日期: 2025-09-19

  修回日期: 2025-11-04

  网络出版日期: 2025-11-11

基金资助

湖南省教育厅基金项目(No. 23B0650), 湖南文理学院重点项目(No. 24ZZ02)和常德市科技创新指导性项目(No. 2025ZD124)资助.

收起

Synthesis of γ-Carbolinone Derivatives via Manganese(III)- Promoted Tandem Phosphinoylation/Cyclization of Activated Alkenes with Phosphites

  • Qiumei Yin ,
  • Jiale Liu ,
  • Shiqiang Deng ,
  • Jiaming Huang ,
  • Jie Jiang ,
  • Yucai Tang
Expand
  • aCollege of Chemistry and Materials Engineering, Hunan Province Engineering Research Center of Electroplating Wastewater Reuse Technology, Hunan University of Arts and Science, Changde 415000

Received date: 2025-09-19

  Revised date: 2025-11-04

  Online published: 2025-11-11

Supported by

Project supported by the Scientific Research Foundation of Hunan Provincial Education Department (No. 23B0650), the Key Research Project of Hunan University of Arts and Sciences (No. 24ZZ02) and the Technology Innovation and Development Guidance Program of Chang De (NO. 2025ZD124).

Fold

摘要

发展了一种锰促进活化烯烃与亚磷酸酯的串联磷酰化/环化反应合成γ-咔啉酮衍生物。该反应表现出较好的底物普适性,一系列N-丙烯酰基-1H-吲哚-3-甲酰胺结构和亚磷酸酯均能顺利实现转化,以中等到优秀的收率得到各种γ-咔啉酮结构化合物,同时该反应可进行放大实验。

关键词： 锰; 烯烃; 亚磷酸酯; 磷酰化/环化; γ-咔啉酮

本文引用格式

印丘梅 , 刘佳乐 , 邓世强 , 黄嘉明 , 蒋洁 , 唐裕才 . 锰促进活化烯烃与亚磷酸酯串联磷酰化/环化反应合成γ-咔啉酮衍生物[J]. 有机化学, 0 : 202509023 -202509023 . DOI: 10.6023/cjoc202509023

Abstract

A manganese(III)-promoted tandem phosphinoylation/cyclization of activated alkenes with phosphites to synthesis γ-carbolinone derivatives has been developed. The present method exhibits excellent compatibility with various N-acryloyl-1H-indole-3-carboxamides and phosphites, and is easy to scale up, providing various γ-carbolinone derivatives in moderate to good yields.

Key words： Manganese; alkenes; phosphites; phosphinoylation/cyclization; γ-carbolinone

参考文献

[1] (a) Somei. M.; Yamada, F. Nat. Prod. Rep.,2005, 22, 73.
(b) Doody R. S.; Gavrilova S. I.; Sano M.; Thomas R. G.; Aisen P. S.; Bachurin S. O.; Seely L.; Hung D. Lancet,2008, 372, 207.
(c) Stempel E.; Gaich, T. Acc. Chem. Res.,2016, 49, 2390.
(d) Singh P. T.; Singh, M. O. Med. Chem.,2018, 18, 9.
(e) Wan Y.; Li Y.; Yan C.; Yan M.; Tang, Z. Eur. J. Med. Chem.,2019, 183, 111691.
(f) Reisenbauer J. C.; Green O.; Franchino A.; Finkelstein P.; Morandi B. Science,2022, 377, 1104.
(g) Lu Y.-H.; Wu C.; Hou J.-C.; Wu Z.-L.; Zhou M.-H.; Huang X.-J.; He W.-M. ACS Catal.,2023, 13, 13071.
(h) Song H.; Jiang, J. ; Wu, C. ; Hou, J.; Lu Y.; Wang K.; Yang T.; He W.-M. Green Chem.,2023, 25, 3292.
(i) Gui Q.; Wang B.; Zhu S.; Li F.; Zhu M.; Yi M.; Yu J.; Wu Z.; He W.-M. Green Chem.,2021, 23, 4430.
(j) Peng Q.; Jiang J.; Liao, Z. ; Wu, Z. ; Ou, L. ; Dai, H.; Peng J.; He, W.-M. ACS Sustainable Chem. Eng.,2025, 13, 10971.
[2] (a) Sun J.; Lou H.; Dai S.; Xu H.; Zhao F.; Liu K. Phytochemistry,2008, 69, 1405.
(b) Sravanthi T. V.; Manju, S. L. Eur. J. Pharm. Sci.,2016, 91, 1.
(c) Dorababu, A. RSC Med. Chem., 2020, 11, 1335.
(d) Zhu Y.; Zhao J.; Luo L.; Gao Y.; Bao H.; Li P.; Zhang, H. Eur. J. Med. Chem.,2021, 223, 113665.
(e) Ji H.; Luo Q.; Wang K.; Ouyang W.; Li H.; He W.-M. Green Chem.,2023, 25, 7983.
(f) Wu Y.; Chen J.; Ning J.; Jiang X.; Deng J.; Deng Y.; Xu R.; He W.-M. Green Chem.,2021, 23, 3950.
(g) Wen Y.; Hou J.; Zhou Q.; Wang S.; Jiang J.; Yang Z.; Zhu H.; Wang Z.; He, W.-M. Chin. Chem. Lett.,2025, 36, 111795.
(h) Peng Q.; Li N.; Hou J.; He C.; Yang Y.; Zhuang C.; Ou L.; Yuan M.; He, W.-M. Chin. Chem. Lett.,2025, 36, 111402.
[3] (a) Cincinelli R.; Cassinelli G.; Dallavalle S.; Lanzi C.; Merlini L.; Botta M.; Tuccinardi T.; Martinelli A.; Penco S.; Zunino, F. J. Med. Chem.,2008, 51, 7777.
(b) Fedorov O.; Huber K.; Eisenreich A.; Filippakopoulos P.; King O.; Bullock A. N.; Szklarczyk D.; Jensen L. J.; Fabbro D.; Trappe J.; Rauch U.; Bracher F.; Knapp S. Chem. Biol.,2011, 18, 67.
[4] Giorgetti A.; Brunetti P.; Haschimi B.; Pulver B.; Pascali J. P.; Riedel J.; Auwärter, V. Drug Test. Anal.,2024, 17, 882.
[5] (a) Abou-Gharbia, M. A. U.S. Patent Appl. US4748247 A, 1988.
(b) Wang, Z.; Li, L.Patent Appl. WO2013/078544 2013.
[6] Shi Z.; Cui Y.; Jiao N. Org. Lett.,2010, 12, 2908.
[7] Mita T.; Ishii S.; Higuchi, Y. ; Sato, Y. Org. Lett.2018, 20, 7603.
[8] Guha S.; Gadde S.; Kumar N.; Black D. S.; Sen, S. J. Org. Chem.,2021, 86, 5234.
[9] Yang D. Y.; Liu L.; Gu J. Y.; He Y. H.; Guan, Z. J. Org. Chem.,2021, 86,18042.
[10] Luo D.; Wang Q.; Liu J.; Mei H.; Han, J. Org. Biomol. Chem.,2025, 23, 1309.
[11] Du Q.; Pan R.; Chen Y.; Tang Y. RSC Adv.,2025, 15, 216.
[12] (a) He, H. W. Phosphorus, Elem., 2008, 183, 266.
(b) Cui S.; Zhang Y.; Wu Q. Chem. Sci.,2013, 4, 3421.
(c) Queffélec C.; Petit M.; Janvier P.; Knight D. A.; Bujoli B. Chem. Rev.,2012, 112, 3777.
(d) Baumgartner T.; Réau R. Chem. Rev.,2006, 106, 4681.
(e) Wei C.-C.; Kong Y.-Y.; Hua X.; Li G.-Q.; Zheng S.-L.; Cheng M.-H.; Wang P.; Miao, C.-Y. Br. J. Pharmacol.,2017, 174, 3823.
[13] (a) Moriarty E.; Carr M.; Bonham S.; Carty M. P.; Aldabbagh, F. Eur. J. Med. Chem.,2010, 45, 3762.
(b) Mai S.; Luo Y.; Huang X.; Shu Z.; Li B.; Lan Y.; Song Q. Chem. Commun.,2018, 54, 10240.
(c) Kochanowska-Karamyan A. J.; Hamann, M. T. Chem. Rev.,2010, 110, 4489.
(d) Li N.; Li C.; Han R.; Wang Y.; Yang M.; Wang H.; Tian, J. Frontiers in Pharmacology.,2019, 10, 53.
[14] (a) Wei W.; Ji, J.-X. Angew. Chem., Int. Ed,.2011, 50, 9097.
(b) Zhou, Y.; Zhou, M.; Chen, M.; Su, J.; Du, J.; Song, Q.RSC Adv. 2015, 5, 103977.
(c) Zhang P.; Zhang L.; Gao Y.; Xu J.; Fang H.; Tang G.; Zhao Y. Chem. Commun.,2015, 51, 7839.
(d) Zhou, Y.; Rao, C.; Mai, S.; Song, Q.J. Org. Chem., 2016, 81, 2027.
(e) Zhou P.; Hu B.; Li L.; Rao K.; Yang J.; Yu, F. J. Org. Chem.,2017, 82, 13268.
[15] (a) Tang, Y.; Liu, J.; Yin, Q.; Huang, J.; Deng, S.; Jiang, J.; He, W.-M. J. Org. Chem., 2025, DOI: 10.1021/acs.joc.5c01775. (b)Tang, Y.; Yang, Y.; Zhou, Q.; Duan, J.; Yang, B.; Du, C.; He, Y. Org. Biomol. Chem., 2023, 21, 5254.
(c) Tang Y.; Duan J.; Yang B.; He Y.; Du C.; Zhang, X. Org. Biomol. Chem.,2023, 21, 8152.
[16] (a) Gui, Q.; Teng, F.; Li, Z.; Xiong, Z.; Jin, X.; Lin, Y.; Cao, Z.; He, W.-M.Chin. Chem. Lett., 2021, 32, 1907.
(b) Liu C.; Zhang Z.; Zhao Z.; Jiang J.; Yang Z.; Wang Z.-L.; He, W.-M. J. Org. Chem.,2025, 90, 11982.
(c) Jiang S.-S.; Xiao Y.-T.; Wu Y.-C.; Luo S.-Z.; Song R.-J.; Li, J.-H. Org. Biomol. Chem.,2020, 18, 4843.
Options
文章导航

/

〈 〉