SIOC English
有机化学
高级检索

有机化学 >

2023 , Vol. 43 >Issue 3: 1146 - 1156

DOI: https://doi.org/10.6023/cjoc202210031

研究论文

二氟卡宾参与下从邻乙烯基苯胺出发构建3-取代吲哚酮类化合物

  • 黄华 ,
  • 李鑫 ,
  • 苏建科 ,
  • 宋秋玲
展开
  • a 华侨大学材料科学工程学院 下一代物质转化研究所 福建厦门 361021
    b 中国科学院上海有机化学研究所 金属有机化学国家重点实验室和有机氟化学重点实验室 上海 200032
    c 河南师范大学化学化工学院 河南新乡 453007

收稿日期: 2022-10-26

  修回日期: 2022-11-30

  网络出版日期: 2022-12-21

基金资助

国家自然科学基金(21931013)

收起

Difluorocarbene-Enabled Synthesis of 3-Substituted-2-oxoindoles from o-Vinylanilines

  • Hua Huang ,
  • Xin Li ,
  • Jianke Su ,
  • Qiuling Song
Expand
  • a Institute of Next Generation Matter Transformation, College of Material Sciences Engineering, Huaqiao University, Xiamen, Fujian 361021
    b State Key Laboratory of Organometallic Chemistry and Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
    c School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
* Corresponding author. E-mail:

Received date: 2022-10-26

  Revised date: 2022-11-30

  Online published: 2022-12-21

Supported by

National Natural Science Foundation(21931013)

Fold

摘要

开发了一种新型的无需过渡金属参与的合成1-烷基-3-(2-氧代-2-芳基/烷基-乙基)吲哚酮的方法. 这项工作揭示了氧吲哚骨架可以直接由邻乙烯基苯胺和市售的卤代二氟烷基试剂通过C—N裂解/新C—N键和C—C键形成来构建. 该反应具有高效和优异的官能团兼容性, 在药物分子和天然产物的后期修饰中具有巨大潜力.

关键词： 卤代二氟试剂; 3-取代吲哚酮; 二氟卡宾

本文引用格式

黄华 , 李鑫 , 苏建科 , 宋秋玲 . 二氟卡宾参与下从邻乙烯基苯胺出发构建3-取代吲哚酮类化合物[J]. 有机化学, 2023 , 43(3) : 1146 -1156 . DOI: 10.6023/cjoc202210031

Abstract

A novel transition-metal-free protocol for the synthesis of 1-alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones is developed. This work reveals that oxoindole skeletons can be directly constructed from ortho-vinylanilines and commercially available halogenated difluoroalkyl reagents via a C—N cleavage/new C—N bonds and C—C bond formation cascade. This reaction portrays high efficiency and excellent functional group compatibility, and has great potential in the late-stage modifications of pharmaceutical molecules and natural products.

Key words： halo difluoro reagent; 3-substituted 2-oxindole; difluorocarbene

参考文献

[1]
(a) Peng, Y.; Keenan, S. M.; Welsh, W. J. J. Mol. Graphics Modell. 2005, 24, 72.
[1]
(b) Bhattacharjee, A. K.; Geyer, J. A.; Woodard, C. L.; Kathcart, A. K.; Nichols, D. A.; Prigge, S. T.; Li, Z.; Mott, B. T.; Waters, N. C. J. Med. Chem. 2004, 47, 5418.
[1]
(c) Woodard, C. L.; Li, Z.; Kathcart, A. K.; Terrell, J.; Gerena, L.; Lopez-Sanchez, M.; Kyle, D. E.; Bhattacharjee, A. K.; Nichols, D. A.; Ellis, W.; Prigge, S. T.; Geyer, J. A.; Waters, N. C. J. Med. Chem. 2003, 46, 3877.
[1]
(d) Kl?ck, C.; Jin, X.; Choi, K.; Khosla, C.; Madrid, P. B.; Spencer, A.; Raimundo, B. C.; Boardman, P.; Lanza, G.; Griffin, J. H. Bioorg. Med. Chem. Lett. 2011, 21, 2692.
[1]
(e) Matheson, C. J.; Casalvieri, K. A.; Backos, D. S.; Minhajuddin, M.; Jordan, C. T.; Reigan, P. Eur. J. Med. Chem. 2020, 197, 112316.
[1]
(f) Edupuganti, R.; Taliaferro, J. M.; Wang, Q.; Xie, X.; Cho, E. J.; Vidhu, F.; Ren, P.; Anslyn, E. V.; Bar-tholomeusz, C.; Dalby, K. N. Bioorg. Med. Chem. 2017, 25, 2609.
[2]
Yong, S. R.; Ung, A. T.; Pyne, S. G.; Skelton, B. W.; White, A. H. Tetrahedron Lett. 2007, 63, 5579.
[3]
Yasuda, D.; Takahashi, K.; Ohe, T.; Nakamura, S.; Mashino, T. Bioorg. Med. Chem. 2013, 21, 7709.
[4]
Lai, J. Y.; Cox, P. J.; Patel, R.; Sadiq, S.; Aldous, D. J.; Thurai- ratnam, S.; Smith, K.; Wheeler, D.; Jagpal, S.; Parveen, S.; Fenton, G.; Harrison, T. K.; McCarthy, C.; Bamborough, P. Bioorg. Med. Chem. 2003, 13, 3111.
[5]
(a) Saito, N.; Kanno, Y.; Yamashita, N.; Degawa, M.; Yoshinari, K.; Nemoto, K. Biol. Pharm. Bull. 2021, 44, 571.
[5]
(b) Sano, M.; Ichimaru, Y.; Kurita, M.; Hayashi, E.; Homma, T.; Saito, H.; Masuda, S.; Nemoto, N.; Hemmi, A.; Suzuki, T.; Miyairi, S.; Hao, H. Cancer Lett. 2017, 397, 72.
[5]
(c) Xie, K.; Chen, R.; Chen, D.; Li, J.; Wang, R.; Yang, L.; Dai, J. Adv. Synth. Catal. 2017, 359, 603.
[5]
(d) Huang, M.; Wang, L.; Zeng, S.; Qiu, Q.; Zou, Y.; Shi, M.; Xu, H.; Liang, L. Inflammation Res. 2017, 66, 433.
[5]
(e) Otlowska, O.; Slebioda, M.; Kot-Wasik, A.; Karczewski, J.; SLiwka-KaszynSka, M. Molecules 2018, 23, 339.
[5]
(f) Aouidate, A.; Ghaleb, A.; Ghamali, M.; Chtita, S.; Ousaa, A.; Choukrad, M.; Sbai, A.; Bouachrine, M.; Lakhlifi, T. Struct. Chem. 2018, 29, 1609.
[5]
(g) Aourz, N.; Serruys, A. K.; Chabwine, J. N.; Balegamire, P. B.; Afrikanova, T.; Edrada-Ebel, R.; Grey, A. I.; Kamuhabwa, A. R.; Walrave, L.; Esguerra, C. V.; Leuven, F. V.; Witte, P. A. M. D.; Smolders, I.; Crawford, A. D. ACS Chem. Neurosci. 2019, 10, 1992.
[5]
(h) Xu, X.; Wei, Y.; Guo, Q.; Zhao, S.; Liu, Z.; Xiao, T.; Liu, Y.; Qiu, Y.; Hou, Y.; Zhang, G.; Wang, K. J. Pharmacol. Exp. Ther. 2018, 365, 624.
[5]
(i) Nguyen, D. T.; Truong, G. N.; Vuong, V. T.; Van, T. N.; Manh, C. N.; Dao, C. T.; Thuy, T. D. T.; Van, C. L.; Khac, V. T. Chem. Pap. 2019, 73, 1083.
[5]
(j) Thakur, R. K.; Joshi, P.; Upadhyaya, K.; Singh, K.; Sharma, G.; Shukla, S. K.; Tripathi, R.; Tripathi, R. P. Eur. J. Med. Chem. 2019, 162, 448.
[5]
(k) Tanaka, T.; Saito, H.; Miyairi, S.; Kobayashi, S. Biochem. Biophys. Res. Commun. 2021, 544, 15.
[5]
(l) Gupta, A. K.; Kalpana, S.; Malik, J. K. Indian J. Pharm. Sci. 2012, 74, 481.
[5]
(m) Dawar, M.; Utreja, D.; Rani, R.; Kaur, K. Lett. Org. Chem. 2020, 17, 199.
[6]
(a) Sohail, M.; Tanaka, F. Angew. Chem., Int. Ed. 2021, 60, 21256.
[6]
(b) Vive-kanand, T.; Vinoth, P.; Agieshkumar, B.; Sampath, N.; Sudalai, A.; Menéndez, J. C.; Sridharan, V. Green Chem. 2015, 17, 3415.
[6]
(c) Zhou, Z.; Wang, Z.; Zhou, Y.; Xiao, W.; Ouyang, Q.; Du, W.; Chen, Y. Nat. Chem. 2017, 9, 590.
[6]
(d) Basu, S.; Mukhopadhyay, C. Eur. J. Org. Chem. 2018, 2018, 1496.
[6]
(e) Parveen, I.; Khan, D.; Ahmed N. Eur. J. Org. Chem. 2019, 2019, 759.
[6]
(f) Halskov, K. S.; Kniep, F.; Lauridsen, V. H.; Iversen, E. H.; Donslund, B. S.; J?rgensen K. A. J. Am. Chem. Soc. 2015, 137, 1685.
[6]
(g) Prieto, L.; Sánchez-Díez, E.; Uria, U.; Reyes, E.; Carrillo, L.; Vicario, L. J. Adv. Synth. Catal. 2017, 359, 1678.
[6]
(h) Faita, G.; Mella, M.; Righetti, P.; Tacconi, G. Tetrahedron 1994, 50, 10955.
[6]
(i) Zhao, B.; Du, D. Adv. Synth. Catal. 2019, 361, 3412.
[6]
(j) Li, D.; Liu, K.; Jiang, Y.; Gu, Y.; Zhang, J.; Zhao, L. Org. Lett. 2018, 20, 1122.
[6]
(k) Fu, Y.; Hu, S.; Li, S.; Li, X. Synth. Commun. 2019, 49, 1067.
[7]
(a) Du, Y.; Li, J.; Chen, K.; Wu, C.; Zhou, Y.; Liu, H. J. Org. Chem. 2017, 13, 1342.
[7]
(b) Biswas, P.; Mandal, S.; Guin, J. Org. Lett. 2020, 22, 4294.
[7]
(c) Fujita, S.; Imagawa, K.; Yamaguchi, S.; Yamasaki, J.; Yamazoe, S.; Mizugaki, T.; Mitsudome, T. Sci. Rep. 2021, 11, 10673.
[8]
(a) Ma, X.; Song, Q. Chem. Soc. Rev. 2020, 49, 9197.
[8]
(b) Dilman, A. D.; Levin, V. V. Acc. Chem. Res. 2018, 51, 1272.
[8]
(c) Liang, H.; Liu, R.; Zhou, M.; Fu, Y.; Ni, C.; Hu, J. Org. Lett. 2020, 22, 7047.
[8]
(d) Smirnov, V. O.; Volodin, A. D.; Korlyukov, A. A.; Dilman, A. D. Angew. Chem.,Int. Ed. 2020, 59, 12428.
[8]
(e) Wang, Y.; Mu, S.; Li, X.; Song, Q. Chin. Chem. Lett. 2020, 33, 1511.
[8]
(f) Ai, H.-J.; Ma, X.; Song, Q.; Wu, X.-F. Sci. China: Chem. 2021, 64, 1630.
[8]
(g) Zhang, X.; Feng, Z.; Min, Q. Org. Lett. 2016, 18, 44.
[8]
(h) Zhang, X.; Feng, Z.; Min, Q.; Fu, X.; An, L. Nat. Chem. 2017, 9, 918.
[8]
(i) Zhang, X.; Houk, K.; Fu, X.; Xue, X.; Zhang, X.; Xiao, Y.; Zhang, S.; Guo, Y. Nat. Chem. 2019, 11, 948.
[9]
Hu, J.; Han, X.; Yuan, Y.; Shi, Z. Angew. Chem., Int. Ed. 2017, 56, 13342.
[10]
(a) Su, J.; Ma, X.; Ou, Z.; Song, Q. ACS Cent. Sci. 2020, 6, 1819.
[10]
(b) Zhang, G.; Shi, Q.; Hou, M.; Yang, K.; Wang, S.; Wang, S.; Li, W.; Li, C.; Qiu, J.; Xu, H.; Zhou, L.; Wang, C.; Li, S.-J.; Lan, Y.; Song, Q. CCS Chem. 2021, 3, 1613.
[10]
(c) Su, J.; Hu, X.; Huang, H.; Guo, Y.; Song, Q. Nat. Commun. 2021, 12, 4986.
[10]
(d) Deng, S.; Song, Q. Chem. Sci. 2019, 10, 6828.
[10]
(e) Ma, X.; Zhou, Y.; Song, Q. Org. Lett. 2018, 20, 4777.
[10]
(f) Ma, X.; Mai, S.; Zhou, Y.; Cheng, G.-J.; Song, Q. Chem. Commun. 2018, 54, 8960.
[10]
(g) Ma, X.; Su, J.; Zhang, X.; Song, Q. iScience 2019, 19, 1.
[10]
(h) Kim, Y.; Heo, J.; Kim, D.; Chang, S.; Seo, S. Nat. Commun. 2020, 11, 4761.
[10]
(i) Mita, T., Harabuchi, Y.; Maeda, S. Chem. Sci. 2020, 11, 7569.
[10]
(j) Nawrot, E.; Jo?czyk, A. J. Org. Chem. 2007, 72, 10258.
[10]
(k) Ma, X.; Huang, H.; Su, J.; Song, Z.; Tamaki, N.; Song, Q. Chin. J. Chem. 2020, 38, 63.
[10]
(l) Sheng, H.; Su, J.; Li, X.; Song, Q. CCS Chem. 2022, 4, 3820.
[11]
(a) Verniest, G.; Colpaert, F.; Hende, E. V.; Kimpe, N. D. J. Org. Chem. 2007, 72, 8569.
[11]
(b) Gilman, H.; Yale, H. L. J. Am. Chem. Soc. 1950, 72, 3646.
[11]
(c) Hende, E. V.; Verniest, G.; Surmont, R.; Kimpe, N. D. Org. Lett. 2007, 9, 2935.
[11]
(d) Eisenstein, O.; Milani, J.; Perutz, R. N. Chem. Rev. 2017, 117, 8710.
[11]
(e) Whittlesey, M. K.; Peris, E. ACS Catal. 2014, 4, 3152.
[11]
(f) Kuehnel, M. F.; Lentz, D.; Braun, T. Angew. Chem., Int. Ed. 2013, 52, 3328.
[11]
(g) Lv, H.; Cai, Y.-B.; Zhang, J.-L. Angew. Chem., Int. Ed. 2013, 52, 3203.
Options
文章导航

/

〈 〉