RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2017; 49(09): 1983-1992
DOI: 10.1055/s-0036-1588376
DOI: 10.1055/s-0036-1588376
paper
Synthesis of 6,7-Dibromoflavone and Its Regioselective Diversification via Suzuki–Miyaura Reactions
Weitere Informationen
Publikationsverlauf
Received: 23. Oktober 2016
Accepted after revision: 20. November 2016
Publikationsdatum:
10. Januar 2017 (online)
Dedicated to the memory of Prof. Tamás Patonay
Abstract
The first synthesis pathway to 6,7-dibromoflavone and its transformations to 7-aryl-6-bromo- and 6,7-diarylflavones by Suzuki–Miyaura reactions are presented. Due to the different electronic effects of bromo substituents, the first attack proceeded with good site selectivity at position 7.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588376.
- Supporting Information
-
References
- 1a Römpp Lexikon Naturstoffe . Steglich W, Fugmann B, Lang-Fugmann S. Thieme; Stuttgart: 1997
- 1b Harborne JB, Baxter H. The Handbook of Natural Flavonoids . Vol. 1. John Wiley and Sons; Chichester: 1999
- 1c Middleton EJr, Kandaswami C, Theoharides TC. Pharmacol. Rev. 2000; 52: 672
- 1d Beecker GR. J. Nutr. 2003; 133: 3248S
- 1e Havsteen BH. Pharmacol. Ther. 2002; 96: 67
- 1f Harborne JB, Williams CA. Phytochemistry 2000; 55: 481
- 2a Gao H, Kawabata J. Bioorg. Med. Chem. 2005; 13: 1661
- 2b Gao GY, Li DJ, Keung WM. J. Med. Chem. 2001; 44: 3320
- 2c Daskiewies J, Depeint F, Viornery L, Bayet C, Geraldine C, Comte G, Gee J, Johnson I, Ndjoko K, Hostettmann K, Barron D. J. Med. Chem. 2005; 48: 2790
- 2d Rao YK, Fang SH, Tzeng YM. Bioorg. Med. Chem. 2005; 13: 6850
- 2e Wang SF, Jiang Q, Ye YH, Li Y, Tan RX. Bioorg. Med. Chem. 2005; 13: 4880
- 2f Kónya K, Pajtás D, Kiss-Szikszai A, Patonay T. Eur. J. Org. Chem. 2015; 828
- 3a Pajtás D, Patonay T, Kónya K. Synthesis 2016; 48: 97
- 3b Kim YW, Hackett JC, Brueggemeier RW. J. Med. Chem. 2004; 47: 4032
- 3c Traxler P, Green J, Mett H, Sequin U, Furet P. J. Med. Chem. 1999; 42: 1018
- 3d Su B, Hackett JC, Diaz-Cruz ES, Kim YW, Brueggemeier RW. Bioorg. Med. Chem. 2005; 13: 6571
- 4a Ahn YM, Vogeti L, Liu C.-J, Santhapuram HK. R, White JM, Vasandani V, Mitscher LA, Lushington GH, Hanson PR, Powell DR, Himes RH, Roby KF, Ye Q, Georg GI. Bioorg. Med. Chem. 2007; 15: 702
- 4b Akama T, Shida Y, Sugaya T, Ishida H, Gomi K, Kasai M. J. Med. Chem. 1996; 39: 3461
- 4c Cushman M, Zhu H, Geahlen RL, Kraker AJ. J. Med. Chem. 1994; 37: 3353
- 4d Larget R, Lockhart B, Renard P, Largeron M. Bioorg. Med. Chem. Lett. 2000; 10: 835
- 5a Konana NA, Lincopana N, Díazb IE. C, Jacysync J.deF, Tibad MM. T, Mendese JG. P. A, Bacchid EM, Spira B. Exp. Toxicol. Pathol. 2012; 64: 435
- 5b Bedir E, Talti II, Khan RA, Zhao J, Takamatsu S, Walker LA, Goldman P, Khan AA. J. Agric. Food Chem. 2002; 50: 3150
- 5c Beara IN, Lesjak MM, Cetojevic-Simin DD, Marjanovic ZS, Ristic JD, Mrkonjic ZO, Mimica-Dukic NM. Food Chem 2014; 165: 460
- 5d Cherry JJ, Rietz A, Malinkevich A, Liu Y, Xie M, Bartolowits M, Davisson VJ, Baleja JD, Androphy EJ. Plos One 2013; 8: e84506
- 5e Park H, Dao TT, Kim HP. Eur. J. Med. Chem. 2005; 40: 943
- 5f Dao TT, Kim SB, Sin K.-S, Kim S, Kim HP, Park H. Arch. Pharmacal Res. 2004; 27: 278
- 5g Lu S, Sun S.-L, Liu H.-C, Chen Y.-D, Yuan H.-L, Gao Y.-P, Lu PY. T. Chem. Biol. Drug Des. 2012; 80: 328
- 5h Finlay MR. V, Griffin RJ. Bioorg. Med. Chem. Lett. 2012; 22: 5352
- 6a Miyaura N, Suzuki A. J. Chem. Soc., Chem. Commun. 1979; 866
- 6b Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 20: 3437
- 7a Beller M, Bolm C. Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals. 2nd ed., Vols. 1-2. Wiley-VCH; Weinheim: 2004
- 7b de Meijere A, Diederich F. Metal-Catalyzed Cross-Coupling Reactions . 2nd ed., Vols. 1-2. Wiley-VCH; Weinheim: 2004
- 7c King AO, Yasuda N. Organometallics in Process Chemistry . Larsen RD. Springer; Berlin: 2004
- 7d Ackermann L. Modern Arylation Methods . Wiley-VCH; Weinheim: 2009
- 7e Tsuji J. Palladium Reagents and Catalysts . 2nd ed. Wiley; Chichester: 2004
- 7f Negishi E.-i. Handbook of Organopalladium for Organic Synthesis . Vols. 1–2. Wiley-Interscience; New York: 2002
- 7g Suzuki A. Modern Arene Chemistry . Astruc D. Wiley-VCH; Weinheim: 2002
- 7h Suzuki A. Pure Appl. Chem. 1985; 57: 1749
- 7i Miyaura N. Top. Curr. Chem. 2002; 219: 11
- 7j Suzuki A. J. Organomet. Chem. 2002; 653: 54
- 7k Corbet J.-P, Mignani G. Chem. Rev. 2006; 106: 2651
- 7l Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev. 2002; 102: 1359
- 7m Yin L, Liebscher J. Chem. Rev. 2007; 107: 133
- 7n Wu XF, Anberasan P, Neumann H, Beller M. Angew. Chem. Int. Ed. 2010; 49: 9047
- 7o Roglans A, Pla-Quintana A, Moreno-Manas M. Chem. Rev. 2006; 106: 4622
- 8a Roy AH, Hartwig JF. Organometallics 2004; 23: 194
- 8b Littke AF, Dai CY, Fu GC. J. Am. Chem. Soc. 2000; 122: 4020
- 8c Hassan Z, Hussain M, Villinger A, Langer P. Tetrahedron 2012; 68: 6305
- 8d Kamikawa T, Hayashi T. Tetrahedron Lett. 1997; 38: 7087
- 8e Hassan Z, Hussain M, Langer P. Synlett 2011; 1827
- 8f Espino G, Kurbangalieva A, Brown JM. Chem. Commun. 2007; 1742
- 9a Wolfe JP, Tomori H, Sadighi JP, Yin J, Buchwald SL. J. Org. Chem. 2000; 65: 1158
- 9b Zapf A, Jackstell R, Rataboul F, Riermeier T, Monsees A, Fuhrmann C, Shaikh N, Dingerdissen U, Beller M. Chem. Commun. 2004; 38
- 9c Rataboul F, Zapf A, Jackstell R, Harkal S, Riermeier T, Monsees A, Dingerdissen U, Beller M. Chem. Eur. J. 2004; 10: 2983
- 9d Nishiyama M, Yamamoto T, Koie Y. Tetrahedron Lett. 1998; 39: 617
- 10a Pajtás D, Dihen K, Kónya K, Langer P. Synlett 2016; 27: 1073
- 10b Wang R, Manabe K. Synthesis 2009; 1405
- 10c Schnürch M, Flasik R, Khan AF, Spina M, Mihovilovic MD, Stanetty P. Eur. J. Org. Chem. 2006; 3283
- 10d Handy ST, Zhang Y. Chem. Commun. 2006; 299
- 11a Pajtás D, Dihen K, Patonay T, Kónya K, Villinger A, Langer P. Synlett 2015; 26: 2601
- 11b Zahid H, Patonay T, Langer P. Synlett 2013; 24: 412
- 11c Eleya N, Malik I, Reimann S, Wittler K, Hein M, Patonay T, Villinger A, Ludwig R, Langer P. Eur. J. Org. Chem. 2012; 1639
- 11d Malik I, Hussain M, Hung NT, Villinger A, Langer P. Synlett 2010; 2244
- 12 Li N, Zhang P, Wu H, Wang J, Liu F, Wang W. J. Funct. Foods 2015; 19: 563
- 13 Benavides A, Bassarello C, Montoro P, Vilegas W, Piacente S, Pizza C. Phytochemistry 2007; 68: 1277
- 14 Sritularak B, Likhitwitayawuid K, Conrad J, Vogler B, Reeb S, Klaiber I, Kraus W. J. Nat. Prod. 2002; 65: 589
- 16a Fekete Sz, Patonay T, Silva AM. S, Cavaleiro JA. S. ARKIVOC 2012; (v): 210
- 16b Chimenti F, Fioravanti R, Bolasco A, Chimenti P, Secci D, Rossi F, Yáñez M, Orallo F, Ortuso F, Alcaro S, Cirilli R, Ferretti R, Sanna ML. Bioorg. Med. Chem. 2010; 18: 1273
- 16c Cabrera M, Simoens M, Falchi G, Lavaggi ML, Piro OE, Castellano EE, Vidal A, Azqueta A, Monge A, Ceráin AL, Sagrera G, Seoane G, Cerecettoa H, González M. Bioorg. Med. Chem. 2007; 15: 3356
- 16d Dao TT, Chi YS, Kim J, Kim HP, Kim S, Park H. Bioorg. Med. Chem. Lett. 2004; 14: 1165
- 17 Lee CK, Yu JS, Lee H.-J. J. Heterocycl. Chem. 2002; 39: 1207
- 18 de Meijere A, Diederich F. Metal-Catalyzed Cross-Coupling Reactions . 2nd ed., Vols. 1-2. Wiley-VCH; Weinheim: 2004
- 19a Donnelly JA, Murphy JJ. J. Chem. Soc. C 1970; 2596
- 19b Chen FC, Chang CT. J. Chem. Soc. 1958; 146
- 20 Tanako D, Fukunaga Y, Doe M, Yoshihara K, Kinoshita T. J. Heterocycl. Chem. 1997; 34: 1111
For reviews of site-selective palladium(0)-catalyzed cross coupling reactions, see:
For a simple guide for predicting the site selectivity of palladium-catalyzed cross-coupling reactions based on 1H NMR spectroscopic data of the nonhalogenated derivatives, see: