SIOC English
有机化学
高级检索

有机化学 >

0 0

DOI: https://doi.org/10.6023/cjoc202506016

研究论文

可见光驱动下卤键诱导的α-碘甲基膦酸二乙酯与香豆素/喹啉酮的直接偶联反应

  • Liang ,
  • Jiarui ,
  • Li ,
  • Jinlan ,
  • Jiang ,
  • Yun ,
  • Yao ,
  • Qiuli ,
  • Xu ,
  • Yingshu ,
  • Wang ,
  • Anjun
展开
  • 遵义医科大学贵州省化学药物创制全省重点实验室 遵义 563000

收稿日期: 2025-06-11

  修回日期: 2025-08-13

  网络出版日期: 2025-09-18

基金资助

遵义市科技计划项目 (遵市科合 HZ 字 (2023) 169 号 ) ,贵州省科技计划项目 (黔科平台人才[2021]1350-005 号) 和贵州省科学技术厅 (黔科合平台人 才-CXTD[2022]012) 资助项目.

收起

Visible-Light-Driven Halogen-Bond-Induced Direct Coupling of Diethyl α-Iodomethylphosphonates with Coumarins/Quinolinones

  • 梁家瑞 ,
  • 李金兰 ,
  • 蒋云 ,
  • 姚秋丽 ,
  • 徐应淑 ,
  • 王安俊
Expand
  • Guizhou Provincial Key Laboratory of Innovation and Manufacturing for Pharmaceuticals, School of Pharmacy, Zunyi Medical University, Zunyi, 563000

Received date: 2025-06-11

  Revised date: 2025-08-13

  Online published: 2025-09-18

Supported by

Zunyi City Science and Technology plan project (Zun City Kehe HZ character [2023]169), Guizhou Province Science and Technology plan project (Guizhou Science Platform talent [2021]1350-005), Science and Technology Department of Guizhou Province (No. QKHPTRC-CXTD2022-012)

Fold

摘要

α-芳基膦酸酯作为一类重要的有机膦化合物,在药物化学中具有重要应用价值;同时,香豆素和喹啉酮也是该领域十分常见的骨架结构。然而,目前α-膦酸化的香豆素/喹啉酮及其衍生物的合成方法十分有限。为此,本文开发了一种可见光驱动下卤键诱导的直接偶联反应,实现了α-碘甲基膦酸二乙酯与香豆素或喹啉酮的高效连接。该反应条件温和、操作简便,且具有优异的底物普适性和区域选择性。

关键词： 可见光; 卤键; α-碘甲基膦酸二乙酯; 香豆素/喹啉酮; 直接偶联反应

本文引用格式

Liang , Jiarui , Li , Jinlan , Jiang , Yun , Yao , Qiuli , Xu , Yingshu , Wang , Anjun . 可见光驱动下卤键诱导的α-碘甲基膦酸二乙酯与香豆素/喹啉酮的直接偶联反应[J]. 有机化学, 0 : 0 . DOI: 10.6023/cjoc202506016

Abstract

α-Aryl phosphonates represent an important class of organophosphorus compounds with significant application value in medicinal chemistry. Meanwhile, coumarin and quinolinone are ubiquitous scaffold structures in this field. However, synthetic methods for α-phosphonylated coumarin/quinolinone derivatives remain limited. To address this, we have developed a visible-light-driven, halogen-bond-induced direct coupling reaction that enables efficient covalent linkage between diethyl α-iodomethylphosphonate and coumarin or quinolinone. This transformation features mild reaction conditions, simple operation, excellent substrate compatibility, and high regioselectivity.

Key words： Visible light; Halogen bond; Diethyl α-Iodomethylphosphonates; Coumarin/Quinolone; Direct coupling reaction

参考文献

[1] (a) Sayed, M. T.; Mady, M. F. Eur. J. Med. Chem. 2025, 286.
(b) Chen, J.; Fan, R.; Liu, Z.; Tan J. Adv. Synth. Catal. 2021, 363(3): 657-667.
(c) Brahmachari, G.; Karmakar, I. J. Org. Chem. 2022, 2022.
(d) Yuan, K.-N.;Xie, T.; Wang, J.-B.; Wang, D.; Shang, M. Angew. Chem. Int. Ed. 2025, e202500744.
(e) Cui, H. -M. PhD Dissertation, University of Ji Lin of China, Changchun, 2024 (in Chinese).
(崔洪铭, 博士论文, 吉林大学, 长春, 2024)
(f) Dzięgielewski, M.; Pięta, J.; Kamińska, E.; Albrecht, L. Eur. J. Org. Chem. 2015, 2015(4): 677-702.
(g) Liu, X.; Zhou, L.; Yang R.; Song, X. R.; Xiao, Q. Adv. Synth. Catal. 2023, 365(14): 2280-2298.
(h) Baughman, R. G.; Hall, G. B. Cryst. Struct. Commun. 2014, 70(10), 975-977.
(i) Hua, X.; Eremin, S. A.; Liu, F.; Wang M. Curr. Org. Chem. 2017, 21(26), 2640-2652.
(j) Lášek, T.; Petrová, M.; Košiová, I.; Šimák, O.; Buděšínský, M.; Kozák, J.; Snášel, J.; Vavřina, Z.; Birkuš, G.; Rosenberg, I. Bioorgan. Med. Chem. 2022, 56: 116632.
(k) Kiiashko, A.; Chaouche, M.; Frouin, L. Cem. Concr. Compos. 2021, 119: 103986.
(l) Zhao, Y. Q.; Liang D.; Jia J. H.; Yu, R. M.; Lu, C.M. Acta Chim. Sinica 2024, 82(5), 486-492. (in Chinese).
(赵雨晴, 梁栋, 贾吉慧, 余荣民, 卢灿忠,化学学报,2024, 82(5), 486-492.)
(m) Gao, Q.; Chen, L. R.; Qian, J. Y.; Fan, R. F.; Sun, W. Q.; Guo, Y. F., Fan, B. M. Acta Chim. Sinica 2024, 82(7), 742-747. (in Chinese).
(高琦, 陈丽蓉, 钱金一, 樊瑞峰, 孙蔚青, 郭亚飞, 樊保敏, 化学学报, 2024, 82(7), 742-747.)
(n) Dong, W. F.; Wang, N.; Yang, H.; Xu, G. Q.; Tang, W. J. Acta Chim. Sinica 2024, 82(9): 940-953. (in Chinese).
(董文锋, 王楠, 杨贺, 徐广庆, 汤文军, 化学学报, 2024, 82(9): 940-953.)
(o) Zhang, Y. D.; Zhu, S. F. Acta Chim. Sinica 2023, 81(7): 777-783. (in Chinese).
(张艳东, 朱守非, 化学学报, 2023, 81(7): 777-783.)
[2] (a) Brodzka, A.; Kowalczyk, P.; Trzepizur, D.; Koszelewski, D.; Kramkowski, K.; Szymczak, M.; Wypych, A.; Lizut, R.; Ostaszewski, R. Molecules. 2022, 27(20): 6865.
(b) Yoshino, K.; Kohno, T.; Uno, T.; Morita, T.; Tsukamoto, G. J.Med. Chem. 1986, 29, 820-825.
[3] Wadsworth W S.; Emmons W D.J. Am. Chem. Soc. 1961, 83(7): 1733-1738.
[4] Boutagy J.; Thomas R. Chem.Rev. 1974, 74(1): 87-99.
[5] (a) Frédérick, R.; Robert, S.; Charlier, C.; de Ruyck J.; Wouters J.; Pirotte B.; Masereel B.; Pochet L. J. Med. Chem. 2005, 48, 7592-7603
(b) Abdelhafez, O. M.; Amin, K. M.; Batran, R. Z.; Maher, T. J.; Nada, S. A.; Sethumadhavan, S. Bioorg. Med. Chem. 2010, 18, 3371-3378.
[6] (a) Yang, X. C.; Zeng, C. M.; Avula, S. R.; Peng, X. M.; Geng, R. X.; Zhou, C. H. Eur. J. Med. Chem. 2023, 245, 114891
(b) Liu, J.; Zhao, S. Y.; Hu, J. Y.; Chen, Q. X.; Jiao, S. M.; Xiao, H. C.; Sun, P. H. J. Med. Chem. 2023, 66, 14735-14754.
(c) Cheke, R. S.; Patel, H. M.; Patil, V. M.; Ansari, I. A.; Ambhore, J. P.; Shinde, S. D.; Deshmukh, P. K. Antibiotics. 2022, 11(5), 566.
(d) Prasoona, G.; Kishore, B.; Brahmeshwari, G. Lett. Org. Chem. 2021, 18(4), 303-310.
[7] (a) Yan, N. L.; Santos-Martins, D.; Nair, R.; Chu, A.; Wilson, I. A.; Johnson, K. A.; Forli, S.; Morgan, G. J.; Petrassi, H. M.; Kelly, J. W. J. Med. Chem. 2021, 64, 6273-6299.
(b) Preisner, A.; Albrecht, S.; Cui, Q. L.; Hucke, S.; Ghelman, J.; Hartmann, C.; Kuhlmann, T. Acta neuropathologica. 2015, 130(2), 247-261.
[8] (a) Zhang, L.; Xu, Z. Eur. J. Med. Chem. 2019, 181: 111587.
(b) Singh, A.; Singh, K.; Kaur, K.; Singh, A.; Sharma, A.; Kaur, K.; Bedi, P. M. S. Biomedicines. 2024, 12(6), 1192.
(c) Song, X. F.; Fan, J.; Liu, L.; Liu, X. F.; Gao, F. Arch. Pharm. 2020, 353(8), 2000025.
(d) Kubrak, T.P.; Makuch-Kocka, A.; Aebisher, D. Pharmaceutics. 2025, 17(5): 595.
(e) Kaur, M.; Kohli, S.; Sandhu, S.; Bansal, Y.; Bansal, G. Anti-Cancer Agent. Me. 2015, 15(8), 1032-1048.
[9] Zhu M.; Ma L.; Wen J.; Dong B.; Wang Y.; Wang Z.; Zhou J.; Zhang G.; Wang J.; Guo Y.; Liang C. Eur.J. Med. Chem. 2020, 186: 111900.
[10] Fang M. C.; Go A. S.; Prasad P. A.; et al.Hsu J. W.; Fan D.; Portugal C.; Sung S. H.; Reynolds K. J. Thromb. Thrombolysis. 2021: 1-9.
[11] Hanna G. J.; Guenette J. P.; Chau N. G.; Sayehli C. M.; Wilhelm C.; Metcalf R.; Wong D. J.; Brose M.; Razaq M.; Pérez‐Ruiz, E.; Cohen, E.E. Cancer. 2020, 126(17): 3972-3981.
[12] Lin T. M.; Chi J. E.; Chang C. C.; Kang Y. N.J. Pain Res. 2018, 83-91.
[13] (a)Xu, Z.; Chen, Q; Zhang, Y.; Liang, C. Fitoterapia. 2021, 150: 104863.
(b) Pu, G.-L., Song, S.-Y., Yang, J., Guo, P., Jia, J., Liu, P.-J., Li,,X.-F., Liu, P., He, C.-Y. Org. Chem. Front. 2024, 11, 3320-3325.
(c) Guo, P.; Pu, G.-L.; Wang, G.-R.; Zeng, L.-Y.; Li, W.-P.; Li, X.-F.; Zhou, P.-P.; He, C.-Y. Org. Lett. 2024, 26, 3097-3102.
(d) Wang, G.-R.; Guo, P.; Pu, G.L.; Wang, P.; Wang, A.-J.; Liu, P.; Jia, J.; Li, X.; He, C.-Y. Org. Chem. Front. 2024, 11, 4722-4729.
(e) Kasperkiewicz, K.; Ponczek, M. B.; Owczarek, J.; Guga, P.; Budzisz, E. Molecules. 2020, 25(6), 1465.
(f) Wang, G.; Sun, S.; Wu, B.; Liu, J. Curr. Top. Med. Chem. 2021, 21(19), 1725-1736.
(g) He, C.-Y.; Kong J.; Li, X.-F.; Li X.; Yao Q.-L.; Yuan F.-M. J. Org. Chem., 2017, 82(2): 910-917.
(h) Hussain, M. K.; Khatoon, S.; Khan, M. F.; Akhtar, M. S.; Ahamad, S.; Saquib, M. Phytomedicine. 2024, 134, 155972.
(i) Mao, T.; Ma, M.-J.; Zhao, L.; Xue, D.-P.; Yu, Y.-B.; Gu, J.-W.; He, C.-Y. Chem. Commun. 2020, 56, 1815-1818.
(j) Bautista-Aguilera, Ó. M.; Ismaili, L.; Chioua, M.; Andrys, R.; Schmidt, M.; Bzonek, P.; Marco-Contelles, J. Int. J. Mol. Sci. 2020, 21(11), 3913.
(k) Tao, M.-L.; Wang, A.-J.; Guo, P.; Li, W.-P.; Zhao, L.; Tong, J.; Wang, H.-Y.; Yu, Y.-B.; He, C.-Y. Adv. Synth. Catal. 2022, 364, 24-29.
(l) Huang, Y.; Wang, A. J.; Kong, J.; Lou, Y. G.; Li, X. F.; He, C. Y. Synthetic Commun. 2018, 48(1), 91-96.
(j) He, X. K.; Lu, J.; Zhang, A. J.; Zhang, Q. Q.; Xu, G. Y.; Xuan, J. Org. Lett. 2020, 22(15), 5984-5989.
[14] Rashamuse T. J.; Musa M. A.; Klein R.; Kaye P. T.J. Chem. Res. Synop. 2009, 2009(5): 302-305.
[15] Abdelli A.; Gaucher A.; Efrit M. L.; M’rabet H. Prim,D. Tetrahedron Lett. 2015, 56(13): 1679-1681
[16] (a) Cavallo, G.; Metrangolo, P.; Milani, R.; Pilati, T.; Priimagi, A.; Resnati, G.; Terraneo, G. Chem. Rev. 2016, 116(4), 2478-2601.
(b) Mamone, M.; Gentile, G.; Dosso, J.; Prato, M.; Filippini, G. Beilstein J. Org. Chem. 2023, 19(1), 575-581.
[17] (a) Chen, Y. L.; Han, W.; Ren, Y. Y.; Ma, M.; Ge, D.; Shen, Z. L.; Chu, X. Q. Adv. Sci. 2025, 12(8), 2404738.
(b) Zhao, L.; Huang, Y.; Wang, Z.; Zhu, E.; Mao, T.; Jia, J.; He, C. Y. Org. Lett. 2019, 21(17), 6705-6709.
(c) Lu, H.; Wang, D. Y.; Zhang, A. J. Org. Chem. 2019, 85(2), 942-951.
(d) Cai, B. G.; Xuan, J.; Xiao, W. J. Sci. Bull. 2019, 64(5), 337-350.
(e) Takeuchi, T.; Minato, Y.; Takase, M.; Shinmori, H. Tetrahedron lett. 2005, 46(52), 9025-9027.
Options
文章导航

/

〈 〉