Synthesis 2014; 46(08): 1100-1106
DOI: 10.1055/s-0033-1340839
paper
© Georg Thieme Verlag Stuttgart · New York

New 4-Pyridyl Nonaflates as Precursors for Push–Pull Solvatochromic Dyes

Moisés Domínguez
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany    Fax: +49(30)83855367   eMail: hans.reissig@chemie.fu-berlin.de
,
Hans-Ulrich Reissig*
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany    Fax: +49(30)83855367   eMail: hans.reissig@chemie.fu-berlin.de
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Publikationsverlauf

Received: 19. Dezember 2013

Accepted after revision: 28. Januar 2014

Publikationsdatum:
21. Februar 2014 (online)


Abstract

2,6-Disubstituted 4-pyridyl nonaflates including methyl, phenyl, 2-thienyl and 2-furyl groups were prepared by cyclocondensation reactions of the appropriate β-ketoenamides. Palladium-catalyzed cross-couplings (Suzuki–Miyaura, Mizoroki–Heck and Sonogashira reactions) led to buildings blocks that are direct precursors for the envisioned synthesis of push–pull solvatochromic dyes.

Supporting Information

 
  • References

    • 1a Reichardt C. Chem. Rev. 1994; 94: 2319
    • 1b Rezende MC. Encyclopedia of Supramolecular Chemistry . Taylor & Francis; Boca Ratón: 2007: 1330
    • 2a El Seoud OA. Pure Appl. Chem. 2009; 81: 697
    • 2b Martins CT, Lima MS, El Seoud OA. J. Org. Chem. 2006; 71: 9068
    • 2c Millán D, Domínguez M, Rezende MC. Dyes Pigments 2008; 77: 441
    • 2d Rezende MC, Oñate R, Núñez G, Domínguez M, Mascayano C. Dyes Pigments 2009; 83: 391
    • 3a Quintana SS, Falcone RD, Silber JJ, Correa NM. ChemPhysChem 2012; 13: 115
    • 3b Durantini AM, Falcone RD, Silber JJ, Correa NM. J. Phys. Chem. B 2011; 115: 5894
    • 3c Aliaga C, Briones L, Rezende MC, Tirapegui C. J. Colloid Interface Sci. 2010; 349: 565
  • 4 Morgan MT, Carnaban MA, Immoos CE, Ribeiro AA, Finkelstein S, Lee SJ, Ginstaff MW. J. Am. Chem. Soc. 2003; 125: 15485
    • 5a Zanotto SP, Scremin M, Machado C, Rezende MC. J. Phys. Org. Chem. 1993; 6: 637
    • 5b Rezende MC, Oñate R, Domínguez M, Millán D. Spectrosc. Lett. 2009; 42: 81
  • 6 Dimroth K, Reichardt C, Siepmann T, Bohlmann F. Liebigs Ann. Chem. 1963; 661: 1
  • 7 Brooker LG. S, Keyes H, Heseltine DW. J. Am. Chem. Soc. 1951; 73: 5350
  • 8 Diemer V, Chaumeil H, Defoin A, Jacques P, Carré C. Tetrahedron Lett. 2005; 46: 4737

    • For a general view about this phenomenon, see:
    • 9a Reichardt C, Welton T. Solvents and Solvent Effects in Organic Chemistry . 4th ed. Wiley-VCH; Weinheim: 2011: 359

    • For reviews on the behavior of compounds such as 1 see:
    • 9b Reichardt C. Pure Appl. Chem. 2004; 76: 1903
    • 9c Reichardt C. Pure Appl. Chem. 2008; 80: 1415
    • 9d Kharlanov V, Rettig W. J. Phys. Chem. A 2009; 113: 10693

    • For further details about the behavior of compounds like 3, see:
    • 9e Jacques P, Graff B, Diemer V, Ay E, Chaumeil H, Carré C, Malval J.-P. Chem. Phys. Lett. 2012; 531: 242
    • 10a Katritzky AR, Zakaria Z, Lunt E. J. Chem. Soc., Perkin Trans. 1 1980; 1879
    • 10b Kjaer AM, Ulstrup J. J. Am. Chem. Soc. 1988; 110: 3874
    • 10c Reichardt C, Eschner M, Schäfer G. J. Phys. Org. Chem. 2001; 14: 737
    • 10d Reichardt C, Che D, Hackenkemper G, Schäfer G. Eur. J. Org. Chem. 2001; 2343
    • 10e Tsubaki K, Morimoto T, Otsubo T, Fuji K. Org. Lett. 2002; 4: 2301
    • 10f Reichardt C, Röchling A, Schäfer G. J. Phys. Org. Chem. 2003; 16: 682
    • 10g Shekhovtsov SV, Omelchenko IV, Dyakomenko VV, Shishkin RA, Libor T, Reichardt C, Mchedlov-Petrossyan N. Dyes Pigments 2012; 92: 1394
    • 10h Gieling RG, Babur M, Mamnani L, Burrows N, Telfer BA, Carta F, Winum J.-Y, Scozzafava A, Supuran CT, Williams KJ. J. Med. Chem. 2012; 55: 5591
    • 11a Arai S, Ymazaki M, Nagakura K, Ishikawa M, Hida M. J. Chem. Soc., Chem. Commun. 1983; 1037
    • 11b van Gent J, Sudhölter EJ. R, Lambeck PV, Popma TJ. A, Gerritsma G, Reinhoudt DN. J. Chem. Soc., Chem. Commun. 1988; 893
    • 11c Wang L.-Y, Zhang X.-G, Shi Y.-P, Zhang Z.-X. Dyes Pigments 2004; 62: 21
    • 11d García-Acosta B, Martínez-Máez R, Ros-Lis JV, Sancenón F, Soto J. Tetrahedron Lett. 2008; 49: 1997
    • 11e Kolev T, Koleva BB, Stoyanov S, Spiteller M, Petkov I. Spectrochim. Acta A: Mol. Biomol. Spectrosc. 2008; 70: 1087
    • 11f Zimmermann-Dimer LM, Reis DC, Machado C, Machado VG. Tetrahedron 2009; 65: 4239
    • 11g Posada P, Braña MF, Villarino AL, Domínguez V, Ortuño I, Martínez C. J. Heterocycl. Chem. 2011; 48: 549
    • 11h Karton-Lifshin N, Albertazzi L, Bendikov M, Baran PS, Shabat D. J. Am. Chem. Soc. 2012; 134: 20412
    • 11i Iliopulos GK, Todorova M, Bakalska R, Penchev P, Sotirov S, Kolev T, Serbezov V, Arbaoui A, Bakasse M, Sahraoui B. J. Phys. Chem. C 2012; 116: 7144
    • 12a Flögel O, Dash J, Brüdgam I, Hartl H, Reissig H.-U. Chem. Eur. J. 2004; 10: 4283
    • 12b Dash J, Lechel T, Reissig H.-U. Org. Lett. 2007; 9: 5541
    • 12c Lechel T, Dash J, Brüdgam I, Reissig H.-U. Eur. J. Org. Chem. 2008; 3647
    • 12d Eidamshaus C, Reissig H.-U. Adv. Synth. Catal. 2009; 351: 1162
    • 12e Dash J, Reissig H.-U. Chem. Eur. J. 2009; 15: 6811
    • 12f Lechel T, Dash J, Hommes P, Lentz D, Reissig H.-U. J. Org. Chem. 2010; 75: 726
    • 12g Lechel T, Dash J, Eidamshaus C, Brüdgam I, Lentz D, Reissig H.-U. Org. Biomol. Chem. 2010; 8: 3007
    • 12h Bera MK, Reissig H.-U. Synthesis 2010; 2129
    • 12i Eidamshaus C, Kumar R, Bera MK, Reissig H.-U. Beilstein J. Org. Chem. 2011; 7: 962
    • 12j Hommes P, Jungk P, Reissig H.-U. Synlett 2011; 2311
    • 12k Hommes P, Berlin S, Reissig H.-U. Synthesis 2013; 45: 3288
    • 12l Bera MK, Domínguez M, Hommes P, Reissig H.-U. Beilstein J. Org. Chem. 2014; 10: 394

      For a review about the advantages of alkenyl and aryl nonaflates in transition-metal-catalyzed reactions, see:
    • 13a Högermeier J, Reissig H.-U. Adv. Synth. Catal. 2009; 351: 2747

    • For recent examples utilizing pyrid-4-yl nonaflates, see:
    • 13b Bera MK, Hommes P, Reissig H.-U. Chem. Eur. J. 2011; 17: 11838
    • 13c Eidamshaus C, Hommes P, Reissig H.-U. Synlett 2012; 23: 1670
    • 13d Gholap SL, Hommes P, Neuthe K, Reissig H.-U. Org. Lett. 2013; 15: 318
    • 13e Bera MK, Gholap SL, Hommes P, Neuthe K, Trawny D, Rabe JP, Lentz D, Zimmer R, Reissig H.-U. Adv. Synth. Catal. 2013; 355: 3463
  • 14 Gao Y, Zhang Q, Xu J. Synth. Commun. 2004; 34: 909
  • 15 Akiba K, Kashiwagi K, Ohyama Y, Yamamoto Y, Ohkata K. J. Am. Chem. Soc. 1985; 107: 2721
    • 16a Zeng F, Zimmerman SC, Kolotuchin S, Reichert DE. C, Ma Y. Tetrahedron 2002; 58: 825
    • 16b Prühs C, Kunick C. Bioorg. Med. Chem. Lett. 2007; 17: 1850
  • 17 Bernhardt S, Kastler M, Enkelmann V, Baumgarten M, Müllen K. Chem. Eur. J. 2006; 12: 6117