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Synthesis 2020; 52(06): 861-872
DOI: 10.1055/s-0039-1690760
DOI: 10.1055/s-0039-1690760
paper
One-Pot Access to 2-Aryl-3-(arylmethyl)chromones
The 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)
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-oneSupporting 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
- 1a Kosmider B, Osiecka R. Drug Dev. Res. 2004; 63: 200
- 1b Teillet F, Boumendjel A, Boutonnat J, Ronot X. Med. Res. Rev. 2008; 28: 715
- 1c Talhi O, Silva AM. S. Curr. Org. Chem. 2012; 16: 859
- 1d Kumazawa Y, Takimoto H, Matsumoto T, Kawaguchi K. Curr. Pharm. Res. 2014; 20: 857
- 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
- 1g Plaskon AS, Grygorenko OO, Ryabukhin SV. Tetrahedron 2012; 68: 2743
- 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
- 1i Snatos CM. M, Silva AM. S. Eur. J. Org. Chem. 2017; 2017: 3115
- 2a Badavath VN, Nath C, Ganta NM, Ucar G, Sinha BN, Jayaprakash V. Chin. Chem. Lett. 2017; 28: 1528
- 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
- 2c Reis J, Gaspar A, Milhazes N, Borges F. J. Med. Chem. 2017; 60: 7941
- 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
- 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
- 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
- 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
- 5b Lee B, Basavarajappa HD, Sulaiman RS, Fei X, Seo S.-Y, Corson TW. Org. Biomol. Chem. 2014; 12: 7673
- 5c Poisson T, Gembus V, Dalla V, Oudeyer S, Levacher V. J. Org. Chem. 2010; 75: 7704
- 5d Mrug GP, Myshko NV, Bondarenko SP, Sviripa VM, Frasinyuk MS. J. Org. Chem. 2019; 84: 7138
- 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
- 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
- 6c Gobbi S, Hu Q, Zimmer C, Engel M, Belluti F, Rampa A, Harmann RW, Bisi A. J. Med. Chem. 2016; 59: 2468
- 7a Raja GC. E, Ryu JY, Lee J, Lee S. Org. Lett. 2017; 19: 6606
- 7b Zhao X, Zhou J, Lin S, Jin X, Liu RC-H. Org. Lett. 2017; 19: 976
- 8a Chang M.-Y, Wu M.-H. Tetrahedron Lett. 2012; 53: 3173
- 8b Chang M.-Y, Wu M.-H, Tai H.-Y. Org. Lett. 2012; 14: 3936
- 8c Chang M.-Y, Wu M.-H. Tetrahedron 2012; 68: 9616
- 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
- 9b Stoyanov EV, Champavier Y, Simon A, Basly J.-P. Bioorg. Med. Chem. Lett. 2002; 12: 2685
- 9c Guo G, Wan S, Si X, Jiang Q, Jia Y, Yang L, Zhou W. Org. Lett. 2017; 19: 5026
- 10a Colombe JR, Bernhardt S, Stathakis C, Buchwald SL, Knochel P. Org. Lett. 2013; 15: 5754
- 10b Štefko M, Slavětínská L, Klepetářová B, Hocek M. J. Org. Chem. 2010; 75: 442
- 10c Wu GG, Wong YS, Poirier M. Org. Lett. 1999; 1: 745
- 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
For reviews, see:
Selected recent examples on biological activities of flavones, see:
For a recent review, see:
Selected examples on biological activities of homoisoflavanones, see:
Selected examples on synthesis of homoisoflavanones and their derivatives, see:
For biological activities of 2-aryl-3-(imidazolylmethyl)chromones, see:
For synthesis of 2-aryl-3-(arylmethyl)chromones, see: