Download PDF
Synlett 2015; 26(11): 1461-1464
DOI: 10.1055/s-0034-1380715
letter
© Georg Thieme Verlag Stuttgart · New York

Gold(I)-Catalyzed Domino Cyclization for the Synthesis of Tricyclic Chromones

Zhiqiang Li
a   College of Pharmacy, Jinan University, Guangzhou, P. R. of China   Email: twmchen@jnu.edu.cn
b   Shenzhen Municipal Key Laboratory of Chemical Synthesis of Medicinal Organic Molecules & Shenzhen Center of Novel Functional Molecules, Shenzhen Research Institute, The Chinese University of Hong Kong, No.10, 2nd Yuexing Road, Shenzhen 518507, P. R. of China
,
Qingjiang Li
c   Department of Chemistry, Centre of Novel Functional Molecules and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. of China   Email: hncwong@cuhk.edu.hk
d   School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China
,
Guo-Kai Liu
b   Shenzhen Municipal Key Laboratory of Chemical Synthesis of Medicinal Organic Molecules & Shenzhen Center of Novel Functional Molecules, Shenzhen Research Institute, The Chinese University of Hong Kong, No.10, 2nd Yuexing Road, Shenzhen 518507, P. R. of China
e   Department of Pharmacy, School of Medicine, Shenzhen University, No.3688, Nanhai Road, Nanshan, Shenzhen 518060, P. R. of China
,
Weimin Chen*
a   College of Pharmacy, Jinan University, Guangzhou, P. R. of China   Email: twmchen@jnu.edu.cn
,
Xiao-Shui Peng
b   Shenzhen Municipal Key Laboratory of Chemical Synthesis of Medicinal Organic Molecules & Shenzhen Center of Novel Functional Molecules, Shenzhen Research Institute, The Chinese University of Hong Kong, No.10, 2nd Yuexing Road, Shenzhen 518507, P. R. of China
c   Department of Chemistry, Centre of Novel Functional Molecules and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. of China   Email: hncwong@cuhk.edu.hk
,
Henry N. C. Wong*
b   Shenzhen Municipal Key Laboratory of Chemical Synthesis of Medicinal Organic Molecules & Shenzhen Center of Novel Functional Molecules, Shenzhen Research Institute, The Chinese University of Hong Kong, No.10, 2nd Yuexing Road, Shenzhen 518507, P. R. of China
c   Department of Chemistry, Centre of Novel Functional Molecules and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. of China   Email: hncwong@cuhk.edu.hk
› Author Affiliations
Further Information

Publication History

Received: 07 March 2015

Accepted after revision: 14 April 2015

Publication Date:
03 June 2015 (online)

    Permissions and Reprints All articles of this category


Abstract

A simple and efficient method for the synthesis of tricyclic chromones has been developed. In this approach, tricyclic chromones were synthesized from a diverse range of phenols and alkynes through a Sonogashira coupling and subsequent gold-catalyzed intramolecular domino cyclization.

Key words

chromone - gold-catalyzed - intramolecular cyclization - domino - Brønsted acid

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380715.
  • Supporting Information
 

  • References and Notes

    • 1a Hepworth JD In Comprehensive Heterocyclic Chemistry . Vol. 3. Katritzky AR, Rees CW. Pergamon Press; Oxford: 1984: 835
      Google Scholar
    • 1b Edwards AM, Howell JB. L. Clin. Exp. Allergy 2000; 30: 756
      Crossref
  • 2 Detty MR. Organometallics 1988; 7: 2188
    Crossref
  • 3 Jovanovic SV, Steenken S, Tosic M, Marjanovic B, Simic MG. J. Am. Chem. Soc. 1994; 116: 4846
    Crossref
  • 4 Martens S, Mithöfer A. Phytochemistry 2005; 66: 2399
    Crossref
  • 5 Zhou T, Shi Q, Lee KH. Tetrahedron Lett. 2010; 51: 4382
    Crossref
  • 6 Kuroda M, Uchida S, Watanabe K, Mimaki Y. Phytochemistry 2009; 70: 288
    CrossrefPubMed
  • 7 Gamal-Eldeen AM, Djemgou PC, Tchuendem M, Ngadjui BT, Tane P, Toshifumi H. Z. Naturforsch., C 2007; 62: 331
  • 8 Borges ML, Matos OC, Pais I, Melo JS. D, Ricardo CP, MacAnita A, Becker RS. Pestic. Sci. 1995; 44: 155
    Crossref
  • 9 Klymchenko AS, Pivovarenko VG, Ozturk T, Demchenko AP. New J. Chem. 2003; 27: 1336
    Crossref
    • 10a Sonar AS, Dandale SG, Solanki PR. J. Chem. Pharm. Res. 2011; 3: 752
    • 10b Wen L, Zhang H, Lin H, Shen Q, Lu L. J. Fluorine Chem. 2012; 133: 171
      Crossref
    • 10c Vedachalam S, Zeng J, Gorityala BK, Antonio M, Liu X.-W. Org. Lett. 2010; 12: 352
      Crossref
    • 10d Vedachalam S, Wong Q.-L, Maji B, Zeng J, Ma J, Liu X.-W. Adv. Synth. Catal. 2011; 353: 219
      Crossref
    • 10e Devitt PF, Timoney A, Vickars MA. J. Org. Chem. 1961; 26: 4941
      Crossref
    • 10f Lubbe M, Appel B, Flemming A, Fischer C, Langer P. Tetrahedron 2006; 62: 11755
      Crossref
  • 11 Yeo JE, Yang XL, Kim HJ, Koo SH. Chem. Commun. 2004; 236
  • 12 Hashmi AS. K. Gold Bull. 2003; 36: 3
    Crossref
    • 13a Nieto-Oberhuber C, Muñoz MP, Buñuel E, Nevado C, Cárdenas DJ, Echavarren AM. Angew. Chem. Int. Ed. 2004; 43: 2402 ; Angew. Chem. 2004, 116, 2456
      CrossrefPubMed
    • 13b Nieto-Oberhuber C, Muñoz MP, López S, Jiménez-Núñnez E, Nevado C, Herrero-Gómez E, Raducan M, Echavarren AM. Chem. Eur. J. 2006; 12: 1677
      Crossref
    • 13c Ferrer C, Raducan M, Nevado C, Claverie CK, Echavarren AM. Tetrahedron 2007; 63: 6306
      Crossref
    • 13d Kaye S, Fox JM, Hicks FA, Buchwald SL. Adv. Synth. Catal. 2001; 343: 789
      Crossref
    • 13e Walker SD, Barder TE, Martinelli JR, Buchwald SL. Angew. Chem. Int. Ed. 2004; 43: 1871 ; Angew. Chem. 2004, 116, 1907
      Crossref
    • 13f Strieter ER, Blackmond DG, Buchwald SL. J. Am. Chem. Soc. 2003; 125: 13978
      Crossref
    • 13g Barder TE, Walker SD, Martinelli JR, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 4685
      Crossref
    • 13h Barder TE, Buchwald SL. J. Am. Chem. Soc. 2007; 129: 5096
      Crossref
    • 13i Kirsch SF. Synthesis 2008; 3183
      Article in Thieme Connect
    • 13j Patil NT, Yamamoto Y. Chem. Rev. 2008; 108: 3395
      CrossrefPubMed
    • 14a Shen HC. Tetrahedron 2008; 64: 3885
      Crossref
    • 14b Belmont P, Parker E. Eur. J. Org. Chem. 2009; 6075
    • 14c Krause N, Belting V, Deutsch C, Erdsack J, Fan H.-T, Gockel B, Hoffmann-Röder A, Morita N, Volz F. Pure Appl. Chem. 2008; 80: 1063
      Crossref
    • 14d Krause N, Aksin-Artok Ö, Breker V, Deutsch C, Gockel B, Poonoth M, Sawama Y, Sawama Y, Sun T, Winter C. Pure Appl. Chem. 2010; 82: 1529
    • 14e Hashmi AS. K, Hutchings GJ. Angew. Chem. Int. Ed. 2006; 45: 7896 ; Angew. Chem. 2006, 118, 8064
      CrossrefPubMed
    • 14f Hashmi AS. K. Chem. Rev. 2007; 107: 3180
      CrossrefPubMed
    • 14g Skouta R, Li C.-J. Tetrahedron 2008; 64: 4917
      Crossref
    • 14h Li Z, Brouwer C, He C. Chem. Rev. 2008; 108: 3239
      CrossrefPubMed
  • 15 Sonogashira K, Tohda Y, Hagihara N. Tetrahedron Lett. 1975; 4467
    • 16a Yu Y, Yang W, Rominger F, Hashmi AS. K. Angew. Chem. Int. Ed. 2013; 52: 7586 ; Angew. Chem.; 2013, 125: 7735
      Crossref
    • 16b Hashmi AS. K, Yang W, Yu Y, Hansmann MM, Rudolph M, Rominger F. Angew. Chem. Int. Ed. 2013; 52: 1329 ; Angew. Chem. 2013, 125, 1368 and references therein
      CrossrefPubMed
  • 17 Synthesis of 2; General Procedure: AuCl(PPh3) (10 mol%) and AgOTf (10 mol%) were added to a stirred solution of 1 (0.2 mmol) in CH2Cl2 (2 mL) under nitrogen at room temperature, and the solution was stirred for 15 min. p-TsOH·H2O (0.2 mmol) was added and the resulting mixture was stirred for 6 h at 40 °C, then cooled to room temperature and the solvent was removed under reduced pressure. The resulting residue was purified by flash column chromatography to give tricyclic chromone 2. Data for 2g: Yield: 56%. 1H NMR (400 MHz, CDCl3): δ = 7.62 (dd, J = 8.4 Hz, 1 H), 7.18 (td, J = 8.0 Hz, 1 H), 6.88 (m, 2 H), 5.44 (t, J = 2.0 Hz, 1 H), 2.69 (m, 1 H), 2.55 (m, 1 H), 2.50 (m, 1 H), 2.21 (m, 1 H); 13C NMR (100 MHz, CDCl3): δ = 180.7, 142.0, 123.4, 123.1, 119.8, 119.7, 112.7, 112.4, 84.7, 31.5, 31.0; HRMS (ESI): m/z [M + Na]+ calcd for C12H9FO2Na: 227.0484; found: 227.0489.
  • 18 Hashmi AS. K. Angew. Chem. Int. Ed. 2010; 49: 5232 ; Angew. Chem. 2010, 122, 5360
    Crossref