Synthesis, Inhaltsverzeichnis Synthesis 2020; 52(06): 861-872DOI: 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 › Institutsangaben Artikel empfehlen Abstract Alle Artikel dieser Rubrik 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 Key wordsaldol condensation - o-hydroxyacetophenones - arylaldehydes - chromones - homoisoflavanone - benzopyran-4-one Volltext Referenzen References For reviews, see: 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 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 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 For a recent review, see: 2c Reis J, Gaspar A, Milhazes N, Borges F. J. Med. Chem. 2017; 60: 7941 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 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 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 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 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 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 For synthesis of 2-aryl-3-(arylmethyl)chromones, see: 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 Zusatzmaterial Zusatzmaterial Supporting Information
