PDF herunterladen
Synthesis 2019; 51(18): 3477-3484
DOI: 10.1055/s-0037-1611850
paper
© Georg Thieme Verlag Stuttgart · New York

Preparation of 2-(3-Methyleneindolin-2-yl)phenols via Sodium Hydride Promoted C–C/C–O Bond Cleavage

Feng-Ping Liu ◊
a   State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, P. R. of China   eMail: moeastlight@mailbox.gxnu.edu.cn
,
Hong-Ping Zhao ◊
a   State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, P. R. of China   eMail: moeastlight@mailbox.gxnu.edu.cn
,
Shuang Tan
a   State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, P. R. of China   eMail: moeastlight@mailbox.gxnu.edu.cn
,
Xiuqiang Lu
b   Fuqing Branch of Fujian Normal University, Fuzhou, Fujian 350300, P. R. of China
,
Dong-Liang Mo  *
a   State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, P. R. of China   eMail: moeastlight@mailbox.gxnu.edu.cn
› InstitutsangabenFinancial support from the National Natural Science Foundation of China (21562005, 51503037), the Natural Science Foundation of Guangxi Province (2016GXNSFFA380005), the Overseas 100 Talents Program of Guangxi Higher Education, and the One Thousand Young and Middle-Aged College and University Backbone Teachers Cultivation Program of Guangxi is greatly appreciated.
Weitere Informationen

Publikationsverlauf

Received: 04. April 2019

Accepted after revision: 13. Mai 2019

Publikationsdatum:
12. Juni 2019 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik


◊ F.-P. Liu and H.-P. Zhao contributed equally to this work.

Abstract

A variety of 2-(3-methyleneindolin-2-yl)phenols were prepared in good to excellent yields through a NaH-promoted C–C/C–O bond cleavage of fused indolines under mild and simple conditions. Mechanistic studies showed that NaH serves as a nucleophile, attacking the aldehyde group of indoline, which is followed by tandem C–C/C–O bond cleavage to afford the desired products. A representative 2-(3-methyleneindolin-2-yl)phenol was easily prepared on a gram scale.

Key words

cascade reaction - C–C/C–O bond cleavage - indolines - phenols - sodium hydride

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611850.
  • Supporting Information
 

  • References

    • 1a Handbook of Reagents for Organic Synthesis, Acidic and Basic Reagents . Reich HJ, Rigby JH. John Wiley & Sons Inc; Hoboken: 1999: 340-343
      Google Scholar
    • 1b Verma A. Synlett 2010; 2361
      Artikel in Thieme Connect
  • 2 Dunn JM. M, Duran-Capece A, Meehan B, Ulis J, Iwama T, Gloor G, Wong G, Bekos E. Org. Process Res. Dev. 2011; 15: 1442
    Crossref

      • For selected examples of NaH used as a base, see:
    • 3a Encyclopedia of Reagents for Organic Synthesis, Vol. 7. Paquette LA. John Wiley & Sons; New York: 1995: 4568-4571
      Google Scholar
    • 3b Zhang Y, Yu A, Jia J, Ma S, Li K, Wei Y, Meng X. Chem. Commun. 2017; 53: 10672
      CrossrefPubMed
    • 3c Tang X, Studer A. Org. Lett. 2016; 18: 4448
      CrossrefPubMed
    • 3d Basceken S, Kaya S, Balci M. J. Org. Chem. 2015; 80: 12552
      CrossrefPubMed
    • 4a Nelson RB, Gribble GW. J. Org. Chem. 1974; 39: 1425
      Crossref
    • 4b Krull LH, Friedman M. Biochem. Biophys. Res. Commun. 1967; 29: 373
      CrossrefPubMed
    • 4c Natsume M, Kumadaki S, Kanda Y, Kiuchi K. Tetrahedron Lett. 1973; 14: 2335
      Crossref
    • 4d Hesek D, Lee M, Noll BC, Fisher JF, Mobashery S. J. Org. Chem. 2009; 74: 2567
      CrossrefPubMed
    • 4e Mao Y, Liu Y, Hu Y, Wang L, Zhang S, Wang W. ACS Catal. 2018; 8: 3016
      Crossref
    • 4f Tejo C, Pang JH, Ong DY, Oi M, Uchiyama M, Takita R, Chiba S. Chem. Commun. 2018; 54: 1782
      CrossrefPubMed
    • 4g Hokamp T, Dewanji A, Lübbesmeyer M, Mück-Lichtenfeld C, Würthwein E, Studer A. Angew. Chem. Int. Ed. 2017; 56: 13275
      CrossrefPubMed
    • 5a Too PC, Chan GH, Tnay YL, Hirao H, Chiba S. Angew. Chem. Int. Ed. 2016; 55: 3719
      CrossrefPubMed
    • 5b Ong DY, Tejo C, Xu K, Hirao H, Chiba S. Angew. Chem. Int. Ed. 2017; 56: 1840
      CrossrefPubMed
    • 5c Huang Y, Chan GH, Chiba S. Angew. Chem. Int. Ed. 2017; 56: 6544
      CrossrefPubMed
    • 5d Kaga A, Hayashi H, Hakamata H, Oi M, Uchiyama M, Takita R, Chiba S. Angew. Chem. Int. Ed. 2017; 56: 11807
      CrossrefPubMed
    • 5e Hong Z, Ong DY, Muduli SK, Too PC, Chan GH, Tnay YL, Chiba S, Nishiyama Y, Hirao H, Soo HS. Chem. Eur. J. 2016; 22: 7108
      CrossrefPubMed
    • 6a Rosso VW, Lust DA, Bernot PJ, Grosso JA, Modi SP, Rusowicz A, Sedergran TC, Simpson JH, Srivastava SK, Humora MJ, Anderson NG. Org. Process Res. Dev. 1997; 1: 311
      Crossref
    • 6b Garrett CE, Prasad K. Adv. Synth. Catal. 2004; 346: 889
      Crossref
  • 7 Ma X.-P, Li K, Wu S.-Y, Liang C, Su G.-F, Mo D.-L. Green Chem. 2017; 19: 5761
    Crossref
    • 8a Leng L, Zhou X, Liao Q, Wang F, Song H, Zhang D, Liu X.-Y, Qin Y. Angew. Chem. Int. Ed. 2017; 56: 3703
      CrossrefPubMed
    • 8b Smith MW, Snyder SA. J. Am. Chem. Soc. 2013; 135: 12964
      CrossrefPubMed
    • 8c Scott AI, Qureshi AA. J. Am. Chem. Soc. 1969; 91: 5874
      CrossrefPubMed
    • 8d Cockrum PA, Colegate SM, Edgar JA, Flower K, Gardner D, Willing RI. Phytochemistry 1999; 51: 153
      Crossref

      For selected examples of the preparation of indoline scaffolds, see:
    • 9a James MJ, O’Brien P, Taylor RJ. K, Unsworth WP. Chem. Eur. J. 2016; 22: 2856
      CrossrefPubMed
    • 9b Liddon JT. R, Rossi-Ashton JA, Taylor RJ. K, Unsworth WP. Org. Lett. 2018; 20: 3349
      CrossrefPubMed
    • 9c Wang P.-F, Jiang C.-H, Wen X, Xu Q.-L, Sun H. J. Org. Chem. 2015; 80: 1155
      CrossrefPubMed
    • 9d Chandrashekhar R, Vemulapalli SP. B, Sridhar B, Reddy BV. S. Eur. J. Org. Chem. 2018; 1693
    • 9e Gao R.-D, Ding L, Zheng C, Dai L.-X, You S.-L. Org. Lett. 2018; 20: 748
      CrossrefPubMed
    • 9f Gan P, Pitzen J, Qu P, Snyder SA. J. Am. Chem. Soc. 2018; 140: 919
      CrossrefPubMed
    • 9g Ren W, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2016; 55: 3500
      CrossrefPubMed
    • 9h Yu Y, Li G, Jiang L, Zu L. Angew. Chem. Int. Ed. 2015; 54: 12627
      CrossrefPubMed
    • 9i Lin A, Yang J, Hashim M. Org. Lett. 2013; 15: 1950
      CrossrefPubMed
    • 9j Wu S.-Y, Chen W.-L, Ma X.-P, Liang C, Su G.-F, Mo D.-L. Adv. Synth. Catal. 2019; 361: 965
      Crossref
    • 9k Dong Z, Zhang X.-W, Li W, Li Z.-M, Wang W.-Y, Zhang Y, Liu W, Liu W.-B. Org. Lett. 2019; 21: 1082
      CrossrefPubMed
    • 9l Wang X, Zhu M.-H, Schuman DP, Zhong D.-Y, Wang W.-Y, Wu L.-Y, Liu W, Stoltz BM, Liu W.-B. J. Am. Chem. Soc. 2018; 140: 10970
      CrossrefPubMed
  • 10 CCDC 1855985 (2a) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.