Synthesis 2016; 48(17): 2863-2872
DOI: 10.1055/s-0035-1562100
paper
© Georg Thieme Verlag Stuttgart · New York

An Efficient One-Pot Two-Step Three-Component Process for the Synthesis of Trifluoromethylated Hydrochromenes

Xufeng Yan
a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
,
Yeqing Yang
a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
,
Jing Han
a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
,
Guimei Jiang
a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
,
Jie Chen
a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
,
Hongmei Deng
b   Laboratory for Microstructures, Instrumental Analysis and Research Center of Shanghai University, Shanghai 200444, P. R. of China
,
Min Shao
b   Laboratory for Microstructures, Instrumental Analysis and Research Center of Shanghai University, Shanghai 200444, P. R. of China
,
Hui Zhang*
a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
b   Laboratory for Microstructures, Instrumental Analysis and Research Center of Shanghai University, Shanghai 200444, P. R. of China
,
Weiguo Cao*
a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
c   Key Laboratory of Synthetic Organic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
d   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 24 January 2016

Accepted after revision: 29 March 2016

Publication Date:
10 May 2016 (online)


Abstract

A one-pot two-step three-component process for the synthesis of trifluoromethylated 2-hydroxy-5-oxo-3,4,5,6,7,8-hexahydro-2H-chromenes has been developed. The three-component reaction of dimedone, substituted benzaldehydes, and methyl 4,4,4-trifluorobut-2-ynoate gave the desired products in moderate to good yields. Excellent regioselectivity and diastereoselectivity were observed. Furthermore, refluxing the product chromenes with p-toluenesulfonic acid in toluene gave the corresponding dehydrated products – trifluoromethylated 5-oxo-5,6,7,8-tetrahydro-4H-chromenes.

Supporting Information

 
  • References

    • 1a Faulkner D. J. Nat. Prod. Rep. 2002; 19: 1
    • 1b Norcross RD, Paterson I. Chem. Rev. 1995; 95: 2041
    • 1c Brioche JC. R, Goodenough KM, Whatrup DJ, Harrity JB. J. Org. Chem. 2008; 73: 1946
    • 1d Kumar S, Malachowski WP, DuHadaway JB, LaLonde JM, Carroll PJ, Jaller D, Metz R, Prendergast GC, Muller AJ. J. Med. Chem. 2008; 51: 1706
    • 1e Yoo NH, Jang DS, Yoo JL, Lee YM, Kim YS, Cho JH, Kim JS. J. Nat. Prod. 2008; 71: 713
    • 2a KamaI-Eldin A, Appelqvist LA. Lipids 1996; 31: 671
    • 2b Tapas AR, Sakarkar DM, Kakde RB. Trop. J. Pharm. Res. 2008; 7: 1089
    • 3a Grisar JM, Petty MA, Bolkenius FN, Dow J, Wagner J, Wagner ER, Haegele KD, Jong WD. J. Med. Chem. 1991; 34: 257
    • 3b Lal J. Contraception 2010; 81: 275
    • 3c Kashiwada Y, Yamazaki K, Ikeshiro Y, Yamagishi T, Fujioka T, Mihashi K, Mizuki K, Cosentino LM, Fowke K, Morris-Natschke SL, Lee K.-H. Tetrahedron 2001; 57: 1559
    • 3d Cassidy F, Evans JM, Hadley MS, Haladij AH, Leach PE, Stemp G. J. Med. Chem. 1992; 35: 1623
    • 3e Comprehensive Heterocyclic Chemistry II . 1st ed., Vol. 5; Katritzky AR, Rees CW, Scriven EF. V. Pergamon Press; Oxford: 1996: 300-500
    • 3f Ellis GP, Lockart IM. The Chemistry of Heterocyclic Compounds, Chromenes, Chromanones and Chromonones. Vol. 31. Wiley-VCH; Weinheim: 2007: 1-1996
    • 4a Zhao J, Sun S, He S, Wu Q, Shi F. Angew. Chem. Int. Ed. 2015; 54: 5460
    • 4b Zhao J, Zhang Y, Xu M, Tang M, Shi F. J. Org. Chem. 2015; 80: 10016
    • 4c Lee A, Scheidt K. Chem. Commun. 2015; 51: 3407
    • 4d Zhang Y, Zhu Q, Yang X, Zhou L, Shi F. J. Org. Chem. 2016; 81: 1681
  • 5 Taylor RR. R, Batey RA. J. Org. Chem. 2013; 78: 1404
  • 6 Dubrovskiy AV, Larock RC. Tetrahedron 2013; 69: 2789
  • 7 Rueping M, Merino E, Bolte M. Org. Biomol. Chem. 2012; 10: 6201
  • 8 Bonacorso HG, Navarini JC, Wiethan W, Bortolotto GP, Paim GR, Cavinatto S, Martins MA. P, Zanatta N, Caro MS. B. J. Fluorine Chem. 2011; 132: 160
  • 9 Song S, Song L, Dai B, Yi H, Jin G, Zhu S, Shao M. Tetrahedron 2008; 64: 5728
  • 10 Duan Y, Wang X, Xu X, Kang Z, Zhang M, Song L, Deng H. Synthesis 2013; 45: 2193
    • 11a Cao L, Shen D, Wei J, Chen J, Deng H, Shao M, Shi J, Zhang H, Cao W. Eur. J. Org. Chem. 2014; 2460
    • 11b Xu Y, Han J, Lu Y, Pan R, Chen J, Deng H, Shao M, Zhang H, Cao W. Tetrahedron 2015; 71: 820
    • 11c Han J, Cao L, Bian L, Chen J, Deng H, Shao M, Jin Z, Zhang H, Cao W. Adv. Synth. Catal. 2013; 355: 1345
  • 12 Lu L, Wei J, Chen J, Zhang J, Deng H, Shao M, Zhang H, Cao W. Tetrahedron 2009; 65: 9152
  • 13 Bian L, Lu X, Xu J, Chen J, Deng H, Shao M, Jin Y, Zhang H, Cao W. Tetrahedron 2013; 69: 6121
    • 14a CCDC 1421261 contains the supplementary crystallographic data of compound 4a for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
    • 14b Unit cell parameters (4a): a: 13.22(3) Å; b: 12.02(2) Å; c: 7.543(6) Å; α: 90°; β: 95.82(3)°; γ: 90°; space group: monoclinic, P2(1)/n.
  • 15 Kaupp G, Naimi-Jamal MR, Schmeyers J. Tetrahedron 2003; 59: 3753
  • 16 Halimehjani AZ, Saidi MR. Tetrahedron Lett. 2008; 49: 1244
    • 17a Gao Y, Yang W, Du DM. Tetrahedron: Asymmetry 2012; 23: 339
    • 17b Tanabe A, Nakashima H, Yoshida O, Yamamoto N, Tenmyo O, Oki T. J. Antibiot. 1988; 41: 1708
    • 17c Bolognese A, Correale G, Manfra M, Lavecchia A, Mazzoni O, Novellino E, La Colla P, Sanna G, Loddo R. J. Med. Chem. 2004; 47: 849
    • 17d Skommer J, Wlodkowic D, Schäfer M, Eray M, Pelkonen J. Leuk. Res. 2006; 30: 322
    • 17e Bayer TA, Schäfer S, Breyhan H, Wirths O, Treiber C, Multhaup G. Clin. Neuropathol. 2006; 25: 163
    • 17f Yu N, Aramini JM, Germann MW, Huang Z. Tetrahedron Lett. 2000; 41: 6993
    • 17g Kumar D, Reddy VB, Sharad S, Dube U, Kapur S. Eur. J. Med. Chem. 2009; 44: 3805
  • 18 Martins MA. P, Cunico W, Brondani S, Peres RL, Zimmermann N, Rose F, Fiss GF, Zanatta N, Bonacorso HG. Synthesis 2006; 1485
  • 19 Pryadeina MV, Kuzueva OG, Burgart YV, Saloutin VI, Lyssenko KV, Antipin MY. J. Fluorine Chem. 2002; 117: 1
    • 20a Hamper BC. J. Org. Chem. 1988; 53: 5558
    • 20b Hamper BC. Org. Synth. 1992; 70: 246