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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 6: 1549 - 1562

DOI: https://doi.org/10.6023/cjoc202004039

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 ,
  • Li Chunpu ,
  • Xu Bin ,
  • Liu Hong
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  • 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 date: 2020-04-25

  Revised date: 2020-04-30

  Online 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).

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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 . DOI: 10.6023/cjoc202004039

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.
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