铜催化2-芳基吲哚酰基化/环化反应合成吲哚[2,1-a]异喹啉酮衍生物

doi:10.6023/cjoc202405027

有机化学

研究论文

铜催化2-芳基吲哚酰基化/环化反应合成吲哚[2,1-a]异喹啉酮衍生物

杨梦娜^a, 唐裕才^a,*, 蒋洁^a, 李佳丽^a, 潘若涵^a, 陈宇^a, 段京林^a, 张松柏^a

^a湖南文理学院化学与材料工程学院, 水处理功能材料湖南省重点实验室,电镀废水回用技术湖南省工程技术研究中心常德 415000

收稿日期:2024-05-21 修回日期:2024-06-26
基金资助:
湖南省教育厅基金项目(No. 23B0650, 23A0503)、湖南省自然科学基金项目(2022JJ30419)和大学生创新创业项目(S202110549001S)资助.

Copper(I)-catalyzed acylation/cyclization of 2-aryl-N-acryloyl indole with benzohydrazides toward indolo[2,1-α]isoquinoline derivatives

Mengna Yang^a, Yucai Tang^a,*, Jie Jiang^a, Jiali Li^a, Ruohan Pan^a, Yu Chen^a, Jinglin Duan^a, Songbai Zhang^a

^aCollege of Chemistry and Materials Engineering, Hunan Provincial Key Laboratory of Water Treatment Functional Materials, Hunan Province Engineering Research Center of Electroplating Wastewater Reuse Technology, Hunan University of Arts and Science, Changde 415000

Received:2024-05-21 Revised:2024-06-26
Contact: *E-mail: yctang1009@163.com
Supported by:
Scientific Research Foundation of Hunan Provincial Education Department (23B0650 and 23A0503), the Natural Science Foundation of Hunan Province (2022JJ30419) and the Innovation and Entrepreneurship Training Program for College Students (S202110549001S).

文章分享

1. 202405027辅助材料.pdf(6148KB)

摘要/Abstract

吲哚[2,1-a]异喹啉酮衍生物是一类重要的生物活性分子, 表现出良好的抗菌活性。本文发展了一种以CuI为催化剂, 叔丁基过氧化氢为氧化剂条件下以2-芳基吲哚和苯甲酰肼为原料,实现不饱和双键的自由基酰基化/环化反应构建吲哚[2,1-a]异喹啉酮衍生物。该方法具有良好的官能团耐受性,一系列酰基取代的吲哚[2,1-a]异喹啉酮类化合物以中等到良好的收率得到 (41 examples)。自由基捕捉实验表明,该反应可能经历了自由基历程。

关键词: 吲哚[2,1-a]异喹啉酮, CuI, 2-芳基吲哚, 苯甲酰肼, 酰基化/环化

Indole[2,1-α]isoquinolines are an important class of bioactive molecules and shows good antibacterial activity. In the present study, an efficient copper(I)-catalyzed acylation/cyclization has been developed for the construction of indolo[2,1-α]isoquinoline derivatives by utilizing 2-aryl-N-acryloyl indole and benzohydrazide as reactants in the presence of CuI as catalyst and tert-butyl hydroperoxide as oxidant. The present protocol exhibits good functional group tolerance and a series of acylated indole[2,1-α]isoquinolines were synthesized in moderate to good yields (41 examples). Radical trapping experiments indicated that the reaction may involve a radical process.

Key words: indolo[2,1-a]isoquinolin-6(5H)-ones, CuI, 2-aryl-N-acryloyl indoles, benzohydrazide, acylation/cyclization

引用此文

杨梦娜, 唐裕才, 蒋洁, 李佳丽, 潘若涵, 陈宇, 段京林, 张松柏. 铜催化2-芳基吲哚酰基化/环化反应合成吲哚[2,1-a]异喹啉酮衍生物[J]. 有机化学, doi: 10.6023/cjoc202405027.

Mengna Yang, Yucai Tang, Jie Jiang, Jiali Li, Ruohan Pan, Yu Chen, Jinglin Duan, Songbai Zhang. Copper(I)-catalyzed acylation/cyclization of 2-aryl-N-acryloyl indole with benzohydrazides toward indolo[2,1-α]isoquinoline derivatives[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202405027.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] (a) Singh, S.; Pathak, N.; Fatima, E.; Negi, A. S. Eur. J. Med. Chem., 2021, 226, 113839.
(b) Bhadra, K.; Kumar, G. S. Med. Res. Rev., 2011, 31, 821.
(c) Plazas, E.; Avila M, M. C.; Mun?oz, D. R.; Cuca S, L. E.; Cuca, S.; L, E. Pharmacol. Res., 2022, 177, 106126.
(d) Hostalkova, A.; Marikova, J.; Opletal, L.; Korabecny, J.; Hulcova, D.; Kunes, J.; Novakova, L.; Perez, D. I.; Jun, D.; Kucera, T.; Andrisano, V.; Siatka, T.; Cahlikova, L. J. Nat. Prod., 2019, 82, 239.Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297.
[2] (a) Tsyrenova, B.; Khrustalev, V.; Nenajdenko, V. J. Org. Chem., 2020, 85, 7024.
(b) Li, C.; Wang, Y.; Wu, S.; Zhuang, W.; Huang, Z.; Zhou, L.; Li, Y.; Chen, M.; You, J. Org. Lett., 2022, 24, 175.
[3] (a) Mohan, C.; Krishna, R. B.; Sivanandan, S. T.; Ibnusaud, I. Eur. J. Org Chem., 2021, 2021, 4911.
(b) Niu, Y.-N.; Xia, X.-F. Org. Biomol. Chem., 2022, 20, 7861.
(c) Zani, L.; Reginato, G.; Mordini, A.; Calamante, M. Synthesis 2016, 48, 3646.
(d) He, R.; Huang, Z.-T.; Zheng, Q.-Y.; Wang, C. Tetrahedron Lett., 2014, 55, 5705.
[4] (a) Wang, C.; Sun, G.; Huang, H.-L.; Liu, J.; Tang, H.; Li, Y.; Hu, H.; He, S.; Gao, F. Chem Asian J., 2021, 16, 2618.
(b) Shen, Z.-J.; Huang, B.; Ma, N.; Yao, L.; Yang, C.; Guo, L.; Xia, W. Adv. Synth. Catal., 2021, 363, 1944.
(c) Zhai, S.; Qiu, S.; Yang, S.; Hua, B.; Niu,Y.; Han, C.; Yu, Y.; Li, Y.; Zhai, H. Chin. Chem. Lett., 2022, 33, 276.
(d) Pan, Y.-L.; Gong, X.-M.; Hao, R.-R.; Zeng, S.-X.; Shen, Z.-R.; Huang, W.-H. RSC Adv., 2022, 12, 9763.
(e) Zhang, J.; Yang, Z.; Yu, J.-T.; Pan, C. Org. Biomol. Chem., 2022, 20, 3067.
[5] Jiang S.-S.; Xiao Y.-T.; Wu Y.-C.; Luo S.-Z.; Song. R.-J.; Li, J.-H. Org. Biomol. Chem., 2020, 18, 4843.
[6] Cui H.; Niu C.; Zhang C. J. Org. Chem., 2021, 86, 15835.
[7] (a) Yu, W.-Q.; Xiong, B.-Q.; Zhong, L.-J.; Liu, Y. Org. Biomol. Chem., 2022, 20, 9659.
(b) Zhang, D.-L.; Zhu, Z.-Q.; Xie, Z.-B.; Zhang, X.-P.; Le, Z.-G. New J. Chem., 2023, 47, 18354.
[8] Zhao P.; Wang Y.; Wang X.; Zhuang D.; Yan R. J. Org. Chem., 2022, 87, 9056.
[9] Luo Y.; Tian T.; Nishihara Y.; Lv L.; Li Z. Chem.Commun., 2021, 57, 9276.
[10] Wei Y.-L.; Chen J.-Q.; Sun B.; Xu P.-F. Chem. Commun., 2019, 55, 5922.
[11] Hu X.-Y.; Xu H.-F.; Chen Q.; Pan Y.-L.; Chen, J.-Z. Org. Biomol. Chem., 2021, 19,10376.
[12] Zeng F.-L.; Xie K.-C.; Liu Y.-T.; Wang H.; Yin P.-C.; Qu L.-B.; Chen X.-L.; Yu B.Green Chem., 2022, 24, 1732.
[13] (a) Li, A. F.; Ruan, Y. B.; Jiang, Q. Q.; He, W. B.; Jiang, Y. B. Chem.-Eur. J., 2010, 16, 5794.
(b) Pouliot, M. F.; Angers, L.; Hamel, J. D.; Paquin, J. F. Org. Biomol. Chem., 2012, 10, 988.
(c) Chauhan, J.; Ravva, M. K.; Sen, S. Org. Lett., 2019, 21, 6562.
(d)Yu, W.; Huang, G.; Zhang, Y. T.; Liu, H. X.; Dong, L. H.; Yu, X. J.; Li, Y. J.; Chang, J. B. J. Org. Chem., 2013, 78, 10337.
(e) Wang, L.; Wang, Y. Y; Chen, Q.; He, M. Y. Tetrahedron Lett., 2018, 59, 1489.
(f) Wang, Q.; Wang, X.; Liu, Q.; Xie, G.; Ding, S.; Wang, X. X; Fan, H. Org. Chem. Front., 2020, 7, 3912.
(g) Shu, W. M.; Zhang, X. Zhang, X. X.; Li, M.; Wang, A. J.; Wu, A. X. J. Org. Chem., 2019, 84, 14919.
(h) Wang, S.; Wang, K.; Kong, X.; Zhang, S.; Jiang, G.; Ji, F. Adv. Synth. Catal., 2019, 361, 3986.
[14] (a) Takale B. S., Telvekar V. N., Chem. Lett.2010, 39,546547
(b) Pal, A., Das, K. M., Sau, S., Thakur, A., Chem Asian J. 2023, 18, e202300755.
[15] (a) Tang, Y.; Duan, J.; Yang, B.; He, Y.; Du, C.; Zhang, X. Org. Biomol. Chem., 2023, 21, 8152.
(b) Tang, Y.; Li, M.; Huang, H.; Wang, F.; Hu, X.; Zhang, X. Synlett 2021, 32, 1219.
(c) Tang, Y.; Dai, K.; Xiang, X.; Yang, Y.; Li, M. Org. Biomol. Chem., 2022, 20, 5704.
[16] (a) Li, X.; Xu, X.; Zhou, C. Chem. Commun., 2012, 48, 12240.
(b) Xu, X.; Tang, Y.; Li, X.; Hong, G.; Fang, M.; Du, X. J. Org. Chem., 2014, 79, 446.
(c) Liu, S.; Zhao, C.; Pan, M.; Liao, H.; Liu, Y.; Zhang, J.; Rong, L. J. Org. Chem., 2023, 88, 16352.
(d) Chen, X.; Ouyang, W.-T.; Li, X.; He, W.-M., Chin. J. Org. Chem., 2023, 43, 4213.
(e) Gui, Q.-W.; Teng, F.; Yu, P.; Wu, Y.-F.; Nong, Z.-B.; Yang, L.-X.; Chen, X.; Yang, T.-B.; W.-M. He, Chin. J. Catal., 2023, 44, 111.
(f) Wang, K.; Huang, J.; Liu, W.; Wu, Z. ; Yu, X.; Jiang, J.; He. W., Chin. J. Org. Chem., 2022, 42, 2527.
(g) Xie, L.-Y.; Peng, S.; Fan, T.-G.; Liu, Y.-F.; Sun, M.; Jiang, L.-L.; Wang, X.-X.; Cao, Z.; He, W.-M. Sci. China Chem., 2019, 62, 460.

铜催化2-芳基吲哚酰基化/环化反应合成吲哚[2,1-a]异喹啉酮衍生物

Copper(I)-catalyzed acylation/cyclization of 2-aryl-N-acryloyl indole with benzohydrazides toward indolo[2,1-α]isoquinoline derivatives

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 7

编辑推荐

相关统计

本文评价

[1]	杜昌远, 唐裕才, 段京林, 杨碧玉, 何宇鹏, 周谦, 刘学文. 可见光促进有机染料催化2-芳基吲哚自由基烷氧羰基化反应研究[J]. 有机化学, 2023, 43(12): 4268-4276.
[2]	马豪杰, 孙洲, 刘金磊, 张夏, 崔华莉, 张玉琦, 王记江. CBr₄促进的分子间环化反应: 高效合成取代N-酰基吡唑[J]. 有机化学, 2021, 41(11): 4353-4360.
[3]	皮超, 曲亚平, 崔秀灵, 吴养洁. 银催化2-芳基吲哚与马来酰亚胺C—H键烷基化反应[J]. 有机化学, 2020, 40(3): 740-747.
[4]	刘瑞婷, 李振, 王圣克, 周锡庚. Pd(OAc)₂/CuI分步催化合成多取代3-烃硫(硒)基吲哚化合物[J]. 有机化学, 2019, 39(11): 3215-3222.
[5]	张文婷, 孙健, 徐飞, 朱红, 岳瑞雪, 张毅, 钮福祥. 离子液体中碘催化下2-氨基苯甲酰肼和4-氧代庚二酸的反应研究[J]. 有机化学, 2017, 37(12): 3191-3197.
[6]	杏朝刚, 俞建忠, 张培志, 吴军. CuI催化的酚与富电子对溴苯甲醚和缺电子间溴苯甲醚的O-芳基化反应研究[J]. 有机化学, 2013, 33(04): 840-847.
[7]	王树良, 盛洁, 屠树江, 王香善. 水介质中Yb(OTf)₃催化下喹唑啉酮衍生物的绿色合成[J]. 有机化学, 2011, 31(9): 1522-1526.