Download PDF
Synthesis 2020; 52(06): 861-872
DOI: 10.1055/s-0039-1690760
paper
© Georg Thieme Verlag Stuttgart · New York

One-Pot Access to 2-Aryl-3-(arylmethyl)chromones

Meng-Yang Chang  ∗
a   Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan
b   Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan   Email: mychang@kmu.edu.tw
,
Kuan-Ting Chen
a   Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan
,
Yu-Lin Tsai
a   Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan
,
Han-Yu Chen
a   Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan
› Author AffiliationsThe authors would like to thank the Ministry of Science and Technology, Taiwan for its financial support (MOST 106-2628-M-037-001-MY3).
Further Information

Publication History

Received: 22 October 2019

Accepted after revision: 14 November 2019

Publication Date:
28 November 2019 (online)

   Permissions and Reprints All articles of this category


Abstract

Sodium hydroxide controlled intermolecular double aldol condensation of o-hydroxyacetophenones with 2 equivalents of aryl­aldehydes provides 2-aryl-3-(arylmethyl)chromones (a chimera of flavone and homoisoflavanone) in MeOH at 50 °C under mild conditions. The uses of various bases and solvents are investigated for one-pot facile and efficient transformation. A plausible mechanism is proposed.

Key words

aldol condensation - o-hydroxyacetophenones - aryl­aldehydes - chromones - homoisoflavanone - benzopyran-4-one

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690760. Included are scanned photocopies of NMR spectral data for all compounds and X-ray analysis data of 4a-4d, 4g, 4t, 4z and 4ag.
  • Supporting Information
 

  • References


      • For reviews, see:
    • 1a Kosmider B, Osiecka R. Drug Dev. Res. 2004; 63: 200
      Crossref
    • 1b Teillet F, Boumendjel A, Boutonnat J, Ronot X. Med. Res. Rev. 2008; 28: 715
      CrossrefPubMed
    • 1c Talhi O, Silva AM. S. Curr. Org. Chem. 2012; 16: 859
      Crossref
    • 1d Kumazawa Y, Takimoto H, Matsumoto T, Kawaguchi K. Curr. Pharm. Res. 2014; 20: 857
      CrossrefPubMed
    • 1e Ibrahim MA, Ali TE, Alnamer YA, Gabr YA. ARKIVOC 2010; (i): 98
    • 1f Gaspar A, Matos MJ, Garrido J, Uriarte E, Borges F. Chem. Rev. 2014; 114: 4960
      CrossrefPubMed
    • 1g Plaskon AS, Grygorenko OO, Ryabukhin SV. Tetrahedron 2012; 68: 2743
      Crossref
    • 1h Li N.-G, Shi Z.-H, Tang Y.-P, Ma H.-Y, Yang J.-P, Li B.-Q, Wang Z.-J, Song S.-L, Duan JA. J. Heterocycl. Chem. 2010; 47: 785
      Crossref
    • 1i Snatos CM. M, Silva AM. S. Eur. J. Org. Chem. 2017; 2017: 3115

      Selected recent examples on biological activities of flavones, see:
    • 2a Badavath VN, Nath C, Ganta NM, Ucar G, Sinha BN, Jayaprakash V. Chin. Chem. Lett. 2017; 28: 1528
      Crossref
    • 2b Charvin D, Pomel V, Ortiz M, Frauli M, Scheffler S, Steinberg E, Baron L, Deshons L, Rudigier R, Thiarc D, Morice C, Manteau B, Mayer S, Graham D, Giethlen B, Brugger N, Hédou G, Conquet F, Schann S. J. Med. Chem. 2017; 60: 8515
      CrossrefPubMed

      • For a recent review, see:
    • 2c Reis J, Gaspar A, Milhazes N, Borges F. J. Med. Chem. 2017; 60: 7941
      CrossrefPubMed

      Selected examples on biological activities of homoisoflavanones, see:
    • 3a Basavarajappa HD, Lee B, Lee H, Sulaiman RS, An H, Magaña C, Shadmand M, Vayl A, Rajashekhar G, Kim EY, Suh Y.-G, Lee K, Seo S.-Y, Corson TW. J. Med. Chem. 2015; 58: 5015
      CrossrefPubMed
    • 3b Zhang H, Yang F, Qi J, Song X.-C, Hu Z.-F, Zhu D.-N, Yu B.-Y. J. Nat. Prod. 2010; 73: 548
      CrossrefPubMed
  • 4 Shen C, Li W, Yin H, Spannenberg A, Skrydstrup T, Wu X.-F. Adv. Synth. Catal. 2016; A leading example on synthesis of flavones, see: 358: 46 ; and references cited therein

      • Selected examples on synthesis of homoisoflavanones and their derivatives, see:
    • 5a Hu H, Chen X, Sun K, Wang J, Liu Y, Liu H, Fan L, Yu B, Sun Y, Qu L, Zhao Y. Org. Lett. 2018; 20: 6157
      CrossrefPubMed
    • 5b Lee B, Basavarajappa HD, Sulaiman RS, Fei X, Seo S.-Y, Corson TW. Org. Biomol. Chem. 2014; 12: 7673
      CrossrefPubMed
    • 5c Poisson T, Gembus V, Dalla V, Oudeyer S, Levacher V. J. Org. Chem. 2010; 75: 7704
      CrossrefPubMed
    • 5d Mrug GP, Myshko NV, Bondarenko SP, Sviripa VM, Frasinyuk MS. J. Org. Chem. 2019; 84: 7138
      CrossrefPubMed

      For biological activities of 2-aryl-3-(imidazolylmethyl)chromones, see:
    • 6a Recanatini M, Bisi A, Cavalli A, Belluti F, Gobbi S, Rampa A, Valenti P, Palzer M, Palusczak A, Hartmann RW. J. Med. Chem. 2001; 44: 672
      CrossrefPubMed
    • 6b Gobbi S, Cavalli A, Rampa A, Belluti F, Piazzi L, Paluszcak A, Hartmann RW, Recanatini M, Bisi A. J. Med. Chem. 2006; 49: 4777
      CrossrefPubMed
    • 6c Gobbi S, Hu Q, Zimmer C, Engel M, Belluti F, Rampa A, Harmann RW, Bisi A. J. Med. Chem. 2016; 59: 2468
      CrossrefPubMed

      For synthesis of 2-aryl-3-(arylmethyl)chromones, see:
    • 7a Raja GC. E, Ryu JY, Lee J, Lee S. Org. Lett. 2017; 19: 6606
      CrossrefPubMed
    • 7b Zhao X, Zhou J, Lin S, Jin X, Liu RC-H. Org. Lett. 2017; 19: 976
      CrossrefPubMed
    • 8a Chang M.-Y, Wu M.-H. Tetrahedron Lett. 2012; 53: 3173
      Crossref
    • 8b Chang M.-Y, Wu M.-H, Tai H.-Y. Org. Lett. 2012; 14: 3936
      CrossrefPubMed
    • 8c Chang M.-Y, Wu M.-H. Tetrahedron 2012; 68: 9616
      Crossref
    • 9a Hofmann E, Webster J, Do T, Kline R, Snider L, Hauser Q, Higginbottom G, Campbell A, Ma L, Paula S. Bioorg. Med. Chem. 2016; 24: 578
      CrossrefPubMed
    • 9b Stoyanov EV, Champavier Y, Simon A, Basly J.-P. Bioorg. Med. Chem. Lett. 2002; 12: 2685
      CrossrefPubMed
    • 9c Guo G, Wan S, Si X, Jiang Q, Jia Y, Yang L, Zhou W. Org. Lett. 2017; 19: 5026
      CrossrefPubMed
    • 10a Colombe JR, Bernhardt S, Stathakis C, Buchwald SL, Knochel P. Org. Lett. 2013; 15: 5754
      CrossrefPubMed
    • 10b Štefko M, Slavětínská L, Klepetářová B, Hocek M. J. Org. Chem. 2010; 75: 442
      CrossrefPubMed
    • 10c Wu GG, Wong YS, Poirier M. Org. Lett. 1999; 1: 745
      CrossrefPubMed
  • 11 CCDC 1896972 (4a), 1896973 (4b), 1896974 (4c), 1896975 (4d), 1896977 (4g), 1896976 (4t), 1896978 (4z), and 1896979 (4ag) contain 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.
  • 12 Wachter-Jurcsak N, Radu C, Redin K. Tetrahedron Lett. 1998; 39: 3903
    Crossref