Cp*Rh(III)-Catalyzed C—H 3,3-Difluoroallylation of Indoles and N-Iodosuccinimide-Mediated Cyclization for the Synthesis of Fluorinated 3,4-Dihydropyrimido-[1,6-a]-indol-1(2H)-one Derivatives

doi:10.6023/cjoc202004039

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1549-1562.DOI: 10.6023/cjoc202004039 Previous Articles Next Articles

铑催化碳氢二氟烯丙基化/N-碘代丁二酰亚胺介导的环化反应构建含氟3,4-二氢嘧啶并[1,6-a]吲哚-1(2H)-酮衍生物

赵森^a,b,c, 李淳朴^b,c, 许斌^a, 柳红^b,c

a 上海大学理学院化学系上海 200444;
b 中国科学院上海药物研究所新药研究国家重点实验室上海 201203;
c 中国科学院上海药物研究所受体结构与功能重点实验室上海 201203

收稿日期:2020-04-25 修回日期:2020-04-30 发布日期:2020-05-08
通讯作者: 许斌, 柳红 E-mail:hliu@simm.ac.cn;xubin@shu.edu.cn
基金资助:
国家自然科学基金（Nos.81620108027，21632008，91229204，81220108025）、中国科学院战略性先导科技专项（Nos.XDA12020375，XDA12050411）资助项目.

Cp*Rh(III)-Catalyzed C—H 3,3-Difluoroallylation of Indoles and N-Iodosuccinimide-Mediated Cyclization for the Synthesis of Fluorinated 3,4-Dihydropyrimido-[1,6-a]-indol-1(2H)-one Derivatives

Zhao Sen^a,b,c, Li Chunpu^b,c, Xu Bin^a, Liu Hong^b,c

a Department of Chemistry, College of Sciences, Shanghai University, Shanghai 200444;
b State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203;
c Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203

Received:2020-04-25 Revised:2020-04-30 Published:2020-05-08
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 81620108027, 21632008, 91229204, 81220108025) and the Strategic Priority Research Program of the Chinese Academy of Sciences (Nos. XDA12020375, XDA12050411).

1. cjoc202004039.pdf(9520KB)

Abstract

A mild and facile two-step strategy has been developed for the synthesis of fluorinated 3,4-dihydropyrimido-[1,6-a]-indol-1(2H)-ones through Cp*Rh(III)-catalyzed C-H 3,3-difluoroallylation and N-iodosuccinimide (NIS)-mediated cyclization. This strategy featured broad synthetic generality, unique versatility and high efficiency, which provided a potential tool for the construction of fluorine-containing heterocycles for drug discovery.

Key words: C-H activation, fluorine chemistry, rhodium catalysis

Cite this article

Zhao Sen, Li Chunpu, Xu Bin, Liu Hong. Cp*Rh(III)-Catalyzed C—H 3,3-Difluoroallylation of Indoles and N-Iodosuccinimide-Mediated Cyclization for the Synthesis of Fluorinated 3,4-Dihydropyrimido-[1,6-a]-indol-1(2H)-one Derivatives[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1549-1562.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Mizuta, M.; Seio, K.; Miyata, K.; Sekine, M. J. Org. Chem. 2007, 72, 5046.
(b) Bandurco, V. T.; Wong, E. M.; Levine, S. D.; Hajos, Z. G. J. Med. Chem. 1981, 24, 1455.
(c) Hammer, H.; Winterfeldt, E. Tetrahedron 1981, 37, 3609.
(d) Kato, M.; Nishino, S.; Iro, K.; Yamakuni, H.; Takasugi, H. Chem. Pharm. Bull. 1994, 42, 2556.
(e) Wright, W. B.; Brabander, H. J. J. Med. Chem. 1968, 11, 1164.
[2] (a) Zhang, Y.; Zheng, J.; Cui, S. J. Org. Chem. 2014, 79, 6490.
(b) Zheng, J.; Zhang, Y.; Cui, S. Org. Lett. 2014, 16, 3560.
(c) Chen, X.; Hu, X.; Bai, S.; Deng, Y.; Jiang, H.; Zeng, W. Org. Lett. 2016, 18, 192.
[3] (a) Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
(b) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
(c) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(d) Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
(e) Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Aceña, J. L.; Soloshonok, V. A.; Izawa, K.; Liu, H. Chem. Rev. 2016, 116, 422.
[4] (a) Price, D. A.; Armour, D.; de Groot, M.; Leishman, D.; Napier, C.; Perros, M.; Stammen, B. L.; Wood, A. Bioorg. Med. Chem. Lett. 2006, 16, 4633.
(b) Xue, F.; Li, H.; Delker, S. L.; Fang, J.; Martásek, P.; Roman, L. J.; Poulos, T. L.; Silverman, R. B. J. Am. Chem. Soc. 2010, 132, 14229.
(c) Zhou, Q.; Ruffoni, A.; Gianatassio, R.; Fujiwara, Y.; Sella, E.; Shabat, D.; Baran, P. S. Angew. Chem., Int. Ed. 2013, 52, 3949.
(d) Massa, M. A.; Spangler, D. P.; Durley, R. C.; Hickory, B. S.; Connolly, D. T.; Witherbee, B. J.; Smith, M. E.; Sikorski, J. A. Bioorg. Med. Chem. Lett. 2001, 11, 1625.
[5] Middleton, W. J.; Bingham, E. M. J. Org. Chem. 1980, 45, 2883.
[6] (a) Fujita, T.; Sugiyama, K.; Sanada, S.; Ichitsuka, T.; Ichikawa, J. Org. Lett. 2016, 18, 248.
(b) S. Akiyama, S.; Kubota, K.; Mikus, M. S.; Paioti, P. H. S.; Romiti, F.; Liu, Q.; Zhou, Y.; Hoveyda, A. H.; Ito, H. Angew. Chem., Int. Ed. 2019, 58, 11998.
(c) Cogswell, T. J.; Dahlen A.; Knerr, L. Chem.-Eur. J. 2019, 25, 1184.
[7] Min, Q. Q.; Yin, Z.; Feng, Z.; Guo, W. H.; Zhang, X. J. Am. Chem. Soc. 2014, 136, 1230.
[8] Li, C.; Zhang, D.; Zhu, W.; Wan, P.; Liu, H. Org. Chem. Front. 2016, 3, 1080.
[9] Ni, J.; Zhao, H.; Zhang, A. Org. Lett. 2017, 19, 3159.
[10] (a) Wu, X.; Wang, B.; Zhou, S.; Zhou, Y.; Liu, H. ACS Catal. 2017, 7, 2494.
(b) Wu, X.; Wang, B.; Zhou, Y.; Liu, H. Org. Lett. 2017, 19, 1294.
(c) Xie, Y.; Wu, X.; Li, C.; Wang, J.; Li, J.; Liu, H. J. Org. Chem. 2017, 82, 5263.
(d) Fei, X.; Li, C.; Yu X.; Liu, H. J. Org. Chem. 2019, 84, 6840.
(e) Yang, L.; Li, C.; Wang, D.; Liu, H. J. Org. Chem. 2019, 84, 7320.
[11] (a) Dai, H.; Yu, C.; Wang, Z.; Yan, H.; Lu, C. Org. Lett. 2016, 18, 3410.
(b) Dutta, U.; Deb, A.; Lupton, D. W.; Maiti, D. Chem. Commun. 2015, 51, 17744.
[12] (a) Zhang, L.; Zhu, M.; Ni, S.; Wen, L.; Li, M. ACS Catal. 2019, 9, 1680.
(b) Kong, W.; Chen, X.; Wang, M.; Dai, H.; Yu, J. Org. Lett. 2018, 20, 284.
[13] Nihei, T.; Iwai, N.; Matsuda, T.; Kitazume, T. J. Org. Chem. 2005, 70, 5912.

[1]	Si Wen, Yuhao Ding, Qingyu Tian, Jin Ge, Guolin Cheng. Rhodium(III)-Catalyzed Synthesis of CF₃-1H-benzo[de][1,8]naph-thyridines via C—H Activation/Annulation of Benzimidates and CF₃-Imidoyl Sulfoxonium Ylides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 291-300.
[2]	Yanbo Zhang, Meng Sun. Rh(III)-Catalyzed C(7)—H Formylmethylation of Indoline with Vinylene Carbonate [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2905-2912.
[3]	Qi Sun, Zeying Sun, Ze Yu, Guangwei Wang. Nickel-Catalyzed Stereoselective Aryl-Difluoroalkylation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2515-2520.
[4]	Xiaojie Liu, Biping Xu, Weiping Su. Rhodium-Catalyzed Decarbonylative Suzuki-Miyaura Cross-Coupling via in-Situ Generation of Acyl Fluorides from Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2184-2191.
[5]	Mengmeng Guo, Zilun Yu, Yulan Chen, Danhua Ge, Mengtao Ma, Zhiliang Shen, Xueqiang Chu. Difluorinated Silyl Enol Ethers as Fluorine-Containing Building Blocks for the Synthesis of Organofluorine Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3562-3587.
[6]	Fengmin Guo, Marko Trajkovski, Qiang Li, Janez Plavec, Zhen Xi, Chuanzheng Zhou. Synthesis and Structure of 4'-CF₃-Uridine Modified Oligoribonucleotides [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4059-4065.
[7]	Li Huaigui, Yang Peng, Xu Zheng, Du Zhengyin, Fu Ying. Cu-Catalyzed Direct Arylation of Benzothiazoles with Diaryliodonium Salts [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2476-2482.
[8]	Wang Hui, Wang Anwei, Xia Zhenzhen, Zhou Weiyou, Sun Zhonghua, Qian Junfeng, He Mingyang. Nickel(Ⅱ)-Catalyzed Aerobic Cross-Dehydrogenative Coupling for the Synthesis of N-Aryl Tetrahydroisoquinolines [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2099-2107.
[9]	Yang Kai, Yao Chen, Gao Juanjuan, Chen Sihong, Zheng Xuejie, Deng Luxuan, Zhang Yu'na, Liu Meijuan, Wang Zhaoyang. Progress on the Synthesis of Pyrido[1,2-a]benzimidazoles [J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4168-4183.
[10]	Wu Yongjie, Shi Bingfeng. Transition Metal-Catalyzed C-H Activation via Imine-Based Transient Directing Group Strategy [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3517-3535.
[11]	Yao Biao, Wu Jiahao, Wang Yu, Jiang Huanfeng. Methods of Transition Metal-Catalyzed Asymmetric Oxidation [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3044-3064.
[12]	Zhang Xiang, Guo Caihong, Wu Haishun. Recent Developments of Homogeneous Transition-Metal Catalysts for Low Temperature Dehydrogenation of Methanol [J]. Chin. J. Org. Chem., 2019, 39(9): 2458-2466.
[13]	Zhang Xiaopeng, Zhu Yanjie, Zhu Yisong, Li Zhengwei, Zhang Guisheng. Advances in Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones [J]. Chin. J. Org. Chem., 2019, 39(9): 2392-2402.
[14]	Wang Yunlong, Zhang Linbao, Niu Junlong, Song Maoping. Copper-Promoted Direct Nitration of Arenes Assisted by an N,O-Bidentate Directing System [J]. Chin. J. Org. Chem., 2019, 39(6): 1761-1766.
[15]	Ji Xiaoming, Shi Guangfa, Zhang Yanghui. Progress of Trifluoromethylation Using Trifluoroacetic Acid and Its Derivatives as CF₃-Sources [J]. Chin. J. Org. Chem., 2019, 39(4): 929-939.

铑催化碳氢二氟烯丙基化/N-碘代丁二酰亚胺介导的环化反应构建含氟3,4-二氢嘧啶并[1,6-a]吲哚-1(2H)-酮衍生物

Cp*Rh(III)-Catalyzed C—H 3,3-Difluoroallylation of Indoles and N-Iodosuccinimide-Mediated Cyclization for the Synthesis of Fluorinated 3,4-Dihydropyrimido-[1,6-a]-indol-1(2H)-one Derivatives

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments