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Synthesis 2014; 46(23): 3239-3248
DOI: 10.1055/s-0034-1379020
DOI: 10.1055/s-0034-1379020
paper
Synthesis of Fluorescent Boron Difluoride Complexes of 3-Acyl-4-hydroxycoumarins
Autoren
Weitere Informationen
Publikationsverlauf
Received: 19. Juni 2014
Accepted after revision: 04. August 2014
Publikationsdatum:
03. September 2014 (online)
Abstract
A series of boron difluoride–3-acyl-4-hydroxycoumarin complexes were synthesized in good yields in three steps starting from 4-hydroxycoumarins. The boron complexes showed strong luminescence in the green–yellow region and are compatible with surface imaging applications.
Supporting Information
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10.1055/s-00000084.
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References
- 1a Ulrich G, Ziessel R, Harriman A. Angew. Chem. Int. Ed. 2008; 47: 1184
- 1b Boens N, Leen V, Dehaen W. Chem. Soc. Rev. 2012; 41: 1130
- 1c Umezawa K, Matsui A, Nakamura Y, Citterio D, Suzuki K. Chem. Eur. J. 2009; 15: 1096
- 1d Olivier J.-H, Widmaier J, Ziessel R. Chem. Eur. J. 2011; 17: 11709
- 2a Kobayayshi H, Ogawa M, Alford R, Choyke PL, Urano Y. Chem. Rev. 2010; 110: 2620
- 2b Louie A. Chem. Rev. 2010; 110: 3146
- 3a Stefane B, Polanc S. Tetrahedron 2007; 63: 10902
- 3b Wang DJ, Xu BP, Wei XH, Zhang J. J. Fluorine Chem. 2012; 140: 49
- 3c Wang DJ, Kang YF, Xu BP, Zheng J, Wei XH. Spectrochim. Acta, Part A 2013; 104: 419
- 4a Trenoe SR, Shultz AR, Love BJ, Long TE. Chem. Rev. 2004; 104: 3059
- 4b Wagner BD. Molecules 2009; 14: 210 ; http://www.mdpi.com/journal/molecules
- 4c Chen J, Liu W, Zhou B, Niu G, Zhang H, Wu J, Wang Y, Ju W, Wang P. J. Org. Chem. 2013; 78: 6121
- 4d Bochkov AY, Akchurin IO, Dyachenko OA, Traven VF. Chem. Commun. 2013; 49: 11653
- 5a Donnelly DM. X, Boland G In The Flavonoids: Advances in Research since 1986 . Horborne JB. Chapman and Hall; New York: 1994: 239
- 5b Venugopala KN, Rashmi V, Odhas B. BioMed Res. Int. 2013; article ID 963248; http://www.hindawi.com/journals/bmri/
- 5c Riveiro ME, De Kimpe N, Moglioni A, Vazquez R, Monczor F, Shayo C, Davio C. Curr. Med. Chem. 2010; 17: 1325
- 6a He J, Chan L, Heber D, Shi W, Lu Q.-Y. J. Nat. Prod. 2006; 69: 121
- 6b Ploypradith P, Mahidol C, Sahakitpichan P, Wongbundit S, Ruchirawat C. Angew. Chem. Int. Ed. 2004; 43: 866
- 6c Ganina OG, Daras E, Bourgarel-Rey V, Peyrot V, Andresyuk AN, Finet J.-P, Fedorov AYu, Beletskaya IP, Combes S. Bioorg. Med. Chem. 2008; 16: 8806
- 6d Combes S, Barbier P, Douillard S, McLeer-Florin A, Bourgarel-Rey V, Pierson J.-T, Fedorov AYu, Finet J.-P, Boutonnat J, Peyrot V. J. Med. Chem. 2011; 54: 3153
- 6e Zou Q, Fang Y, Zhao Y, Zhao H, Wang Y, Gu Y, Wu F. J. Med. Chem. 2013; 56: 5288
- 6f Pérez-Cruz F, Vazquez-Rodriguez S, Matos MJ, Herrera-Morales A, Villamena FA, Das A, Gopalakrishnan B, Olea-Azar C, Santana L, Uriarte E. J. Med. Chem. 2013; 56: 6136
- 7 Fedorov AYu, Nyuchev AV, Beletskaya IP. Chem. Heterocycl. Compd. (N. Y., NY, U. S.) 2012; 48: 166
- 8a Murakami H, Hohsaka T, Ashizuka Y, Hashimoto K, Sisido M. Biomacromolecules 2000; 1: 118
- 8b Coleman RS, Berg MA, Murphy CJ. Tetrahedron 2007; 63: 3450
- 8c Coleman RS, Madaras ML. J. Org. Chem. 1998; 63: 5700
- 9a Giguere D, Sato S, St-Pierre C, Sirois S, Roy R. Bioorg. Med. Chem. Lett. 2006; 16: 1668
- 9b Giguere D, Patnam R, Bellefleur M.-A, St-Pierre C, Sato S, Roy R. Chem. Commun. 2006; 2379
- 10a Manca F. J. Immunol. 1992; 148: 2278
- 10b Luciani A, Olivier J.-C, Clement O, Siauve N, Brillet P.-Y, Gazeau F, Uchegbu IF, Frija G, Cuenod CA. Radiology 2004; 231: 135
- 10c Forthal DN, Gach JS, Landucci G, Jez J, Strasser R, Kunert R, Steinkellner H. J. Immunol. 2010; 185: 6876
- 11a Barton DH. R, Donnelly DM. X, Finet J.-P, Guiry PG. J. Chem. Soc., Perkin Trans. 1 1992; 1365
- 11b Bailly C, Bal C, Barbier P, Combes S, Finet J.-P, Hildebrand M.-P, Peyrot V, Wattez N. J. Med. Chem. 2003; 46: 5437
- 11c Beletskaya IP, Ganina OG, Tsvetkov AV, Fedorov AYu, Finet J.-P. Synlett 2004; 2797
- 12 Tornøe CW, Christensen C, Mendal M. J. Org. Chem. 2002; 67: 3057
- 13a Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
- 13b Worrell BT, Malik JA, Fokin VV. Science (Washington, D. C.) 2013; 340: 457
- 14a Bock VD, Hiemstra H, van Maarseveen JH. Eur. J. Org. Chem. 2006; 51
- 14b Wu P, Fokin VV. Aldrichimica Acta 2007; 40: 7
- 14c Lutz J.-F. Angew. Chem. Int. Ed. 2007; 46: 1018
- 14d Meldal M, Tornøe CW. Chem. Rev. 2008; 108: 2952
- 14e Amblard F, Cho JH, Schinazi RF. Chem. Rev. 2009; 109: 4207
- 14f Hein JE, Fokin VV. Chem. Soc. Rev. 2010; 39: 1302
- 15a Stefanou V, Matiadis D, Melagraki G, Afantitis A, Athanasellis G, Igglessi-Markopoulou O, McKee V, Markopoulos J. Molecules 2011; 16: 384 ; http://www.mdpi.com/journal/molecules
- 15b Melagraki G, Afantitis A, Igglessi-Markopoulou O, Detsi A, Koufaki M, Kontogiorgis C, Hadjipavlou-Litina DJ. Eur. J. Med. Chem. 2009; 44: 3020
- 16a Cravotto G, Tagliapietra S, Cappello R, Palmisano G, Curini M, Boccalini M. Arch. Pharm. (Weinheim, Ger.) 2006; 339: 129
- 16b Ferroud D, Haesslein J.-L, Klich M, Laurin P, Musicki B, Periers A.-M, Bonnefoy A, Dupuis-Hamelin C, Lassaigne P, Mauvais P. Bioorg. Med. Chem. Lett. 2000; 10: 161
- 16c Ferroud D, Klich M, Laurin P, Musicki B, Bonnefoy A, Dupuis-Hamelin C, Lassaigne P, Mauvais P. Bioorg. Med. Chem. Lett. 1999; 9: 2079
- 16d Iaroshenko VO, Erben F, Mkrtchyan S, Hakobyan A, Vilches-Herrera M, Dudkin S, Bunescu A, Villinger A, Sosnovskikh VYa, Langer P. Tetrahedron 2011; 67: 7946
- 16e Hojas G, Stadlbauer W. J. Heterocycl. Chem. 2004; 41: 681
- 17a Kotali A, Nasiopoulou DA, Harris PA, Helliwell M, Joule JA. Tetrahedron 2012; 68: 761
- 17b Hamdi N, Fischmeister C, Puerta MC, Valerga P. Med. Chem. Res. 2011; 20: 522
- 17c Manaev AV, Chibisova TA, Lyssenko KA, Antipin MYu, Traven VF. Russ. Chem. Bull. 2006; 55: 2091
- 17d Trivedi JC, Bariwal JB, Upadhyay KD, Naliapara YT, Joshi SK, Pannecouque CC, De Clercq E, Shah AK. Tetrahedron Lett. 2007; 48: 8472
- 18 Chen Y.-S, Kuo P.-Y, Shie T.-L, Yang D.-Y. Tetrahedron 2006; 62: 9410
- 19 Parenty A, Moreau X, Niel G, Campagne J.-M. Chem. Rev. 2013; 113: PR1
- 20 Jones II G, Jackson WR, Choi CY, Bergmack WR. J. Phys. Chem. 1985; 89: 294
- 21 Nyuchev AV, Sharonova EA, Lenshina NA, Shavyrin AS, Lopatin MA, Balalaeva IV, Beletskaya IP, Fedorov AYu. Tetrahedron Lett. 2011; 52: 4196
- 22 Brotherton WS, Michaels HA, Simmons JT, Clark RJ, Dalal NS, Zhu L. Org. Lett. 2009; 11: 4954
- 23a Gerasov AO, Zyabrev KV, Shandura MP, Kovtun YP. Dyes Pigm. 2011; 89: 76
- 23b D’Aléo A, Gachet D, Heresanu V, Giorgi M, Fages F. Chem. Eur. J. 2012; 18: 12764
- 24 Celli JP, Spring BQ, Rizvi I, Evans CL, Samkoe KS, Verma S, Pogue BW, Hasan T. Chem. Rev. 2010; 110: 2795
- 25 Combes S, Finet J.-P, Siri D. J. Chem. Soc., Perkin Trans. 1 2002; 38