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Synthesis 2009(16): 2697-2708  
DOI: 10.1055/s-0029-1216873
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile and Efficient Synthesis of a New Class of Indole-Substituted Pyridine Derivatives via One-Pot Multicomponent Reactions

Kai Zhao, Xiao-Ping Xu, Song-Lei Zhu, Da-Qing Shi, Yong Zhang, Shun-Jun Ji*
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China
Fax: +86(512)65880307; e-Mail: chemjsj@suda.edu.cn;
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Publication History

Received 18 March 2009
Publication Date:
26 June 2009 (online)

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Abstract

A new series of indole-containing pyridine derivatives, 4-aryl-6-(1H-indol-3-yl)-2,2′-bipyridine-5-carbonitriles, were synthesized via one-pot multicomponent reactions of 3-(cyano­acetyl)indoles, aldehydes, heterocyclic ketones, and ammonium acetate. Particularly valuable features of this method include high yields of products, broad substrate scope, and straightforward procedures.

Key words

pyridine derivatives - indole - one-pot synthesis - multicomponent reactions - heterocycles

    References

  • 1 Yates F. Courts RT. Casy AF. Pyridine and Its Derivatives: Supplement IV   Abramovitch RA. Wiley; New York: 1975.  p.445 
    Google Scholar
  • 2 Yates FS. Comprehensive Heterocyclic Chemistry   Vol. 2:  Katritzky AR. Rees CW. Pergamon; Oxford: 1984.  p.511 
    Google Scholar
  • 3a Dowell RI. Hales NJ. Tucker H. Eur. J. Med. Chem.  1993,  28:  513 
    Google Scholar
  • 3b Zhou X.-W. Zhuang Z.-L. Chen Q.-X. J. Protein Chem.  1999,  18:  735 
    Google Scholar
  • 3c Zhang B. Breslow R. J. Am. Chem. Soc.  1998,  120:  5854 
    Google Scholar
  • 4a Constable EC. Tetrahedron  1992,  48:  10013 
    Google Scholar
  • 4b Sauvage JP. Collin JP. Chambron JC. Guillerez S. Coudret C. Balzani V. Barigelletti F. De Cola L. Flamigni L. Chem. Rev.  1994,  94:  993 
    Google Scholar
  • 4c Bernhard S. Barron JA. Houston PL. Abruna HD. Ruglovksy JL. Gao X. Malliaras GG. J. Am. Chem. Soc.  2002,  124:  13624 
    Google Scholar
  • 4d Newkome GR. Patri AK. Holder E. Schubert US. Eur. J. Org. Chem.  2004,  235 
    Google Scholar
  • 5a Namba K. Cui S. Wang J. Kishi Y. Org. Lett.  2005,  7:  5417 
    Google Scholar
  • 5b Namba K. Wang J. Cui S. Kishi Y. Org. Lett.  2005,  7:  5421 
    Google Scholar
  • 6a Juris A. Balzani V. Barigelletti F. Campagna S. Belser A. von Zelewsky A. Coord. Chem. Rev.  1988,  84:  85 
    Google Scholar
  • 6b Balzani V. Juris A. Venturi M. Campagna S. Serroni S. Chem. Rev.  1996,  96:  759 
    Google Scholar
  • 7 Meyer TJ. Acc. Chem. Res.  1989,  22:  163 
    CrossrefGoogle Scholar
  • 8a Dupray LM. Devenney M. Striplin DR. Meyer TJ. J. Am. Chem. Soc.  1997,  119:  10243 
    Google Scholar
  • 8b Newkome GR. Patri AK. Godinez LA. Chem. Eur. J.  1999,  5:  1445 
    Google Scholar
  • 8c Constable EC. Harverson P. Oberholzer M. Chem. Commun.  1996,  1821 
    Google Scholar
  • 9a Schubert US. Eschbaumer C. Heller M. Org. Lett.  2000,  2:  3373 
    Google Scholar
  • 9b Tu S.-J. Jiang B. Yao C.-S. Jiang H. Zhang J.-Y. Jia R.-H. Zhang Y. Synthesis  2007,  1366 
    Google Scholar
  • 9c Tu S.-J. Jiang B. Zhang Y. Zhang J.-Y. Jia R.-H. Yao C.-S. Chem. Lett.  2006,  35:  1338 
    Google Scholar
  • 10 Houlihan WJ. Remers WA. Brown RK. Indoles: Part I   Wiley; New York: 1992. 
    Google Scholar
  • 11a Creed D. Photochem. Photobiol.  1984,  39:  537 
    Google Scholar
  • 11b Gupta L. Talwar A. Palne NS. Gupta S. Chauhan PMS. Bioorg. Med. Chem. Lett.  2007,  17:  4075 
    Google Scholar
  • 11c Jiang B. Xiong X. Yang C. Bioorg. Med. Chem. Lett.  2001,  11:  475 
    Google Scholar
  • 11d Sakemi S. Sun HH. J. Org. Chem.  1991,  56:  4304 
    Google Scholar
  • 12a Yan C.-G. Wang Q.-F. Song X.-K. Sun J. J. Org. Chem.  2009,  74:  710 
    Google Scholar
  • 12b Wang S.-Y. Ji S.-J. Synlett  2007,  2222 
    Google Scholar
  • 12c Zhu S.-L. Ji S.-J. Zhang Y. Tetrahedron  2007,  63:  9365 
    Google Scholar
  • 12d Wang S.-Y. Ji S.-J. Tetrahedron  2006,  62:  1527 
    Google Scholar
  • 13a Lo KK.-W. Tsang KH.-K. Hui W.-K. Zhu N. Chem. Commun.  2003,  44:  2704 
    Google Scholar
  • 13b Lo KK.-W. Tsang KH.-K. Hui W.-K. Zhu N. Inorg. Chem.  2005,  44:  6100 
    Google Scholar
  • 13c Bowyer PK. Black DStC. Craig DC. Rae AD. Willis AC. J. Chem. Soc., Dalton Trans.  2001,  1948 
    Google Scholar
  • 14a Kröehnke F. Angew. Chem., Int. Ed. Engl.  1963,  2:  380;  Angew. Chem. 1963, 75, 317
    Google Scholar
  • 14b Kröehnke F. Synthesis  1976,  1 
    Google Scholar
  • 15a Rode T. Breitmaier E. Synthesis  1987,  574 
    Google Scholar
  • 15b Baxter PNW. Connor JA. J. Organomet. Chem.  1988,  355:  193 
    Google Scholar
  • 15c Vögtle F. Hochberg R. Kochendoerfer F. Windscheif PM. Volkmann M. Jansen M. Chem. Ber.  1990,  123:  2181 
    Google Scholar
  • 15d Percec V. Barboiu B. Kim H.-J. J. Am. Chem. Soc.  1998,  120, 305 
    Google Scholar
  • 16a Uchida Y. Kajita R. Kawasaki Y. Oae S. Tetrahedron Lett.  1995,  36:  4077 
    Google Scholar
  • 16b Uchida Y. Kozawa H. Tetrahedron Lett.  1989,  30:  6365 
    Google Scholar
  • 16c Uchida Y. Onoue K. Tada N. Nagao F. Tetrahedron Lett.  1989,  30:  567 
    Google Scholar
  • 16d Newkome GR. Hager DC. J. Am. Chem. Soc.  1978,  100:  5567 
    Google Scholar
  • 17a Furukawa N. Shibutani T. Fujihara H. Tetrahedron Lett.  1989,  30:  7091 
    Google Scholar
  • 17b Oae S. Takeda T. Wakabayashi S. Tetrahedron Lett.  1988,  29:  4445 
    Google Scholar
  • 17c Kawai T. Furukawa N. Tetrahedron Lett.  1984,  25:  2549 
    Google Scholar
  • 18a Ishikura M. Kamada M. Terashima M. Synthesis  1984,  936 
    Google Scholar
  • 18b Lehmann U. Henze O. Schlüter D. Chem. Eur. J.  1999,  5:  854 
    Google Scholar
  • 19 Savage SA. Smith AP. Fraser CL. J. Org. Chem.  1998,  63:  10048 
    CrossrefGoogle Scholar
  • 20 Zhu S.-L. Ji S.-J. Su X.-M. Sun C. Liu Y. Tetrahedron Lett.  2008,  49:  1777 
    CrossrefGoogle Scholar
  • 21 Kreher R. Wagner PH. Chem. Ber.  1980,  113:  3675 
    CrossrefGoogle Scholar
  • 22 Slatt J. Romero I. Bergman J. Synthesis  2004,  2760 
    Article in Thieme ConnectGoogle Scholar
  • 23a Devi I. Kumarb BSD. Bhuyan PJ. Tetrahedron Lett.  2003,  44:  8307 
    Google Scholar
  • 23b Evdokimov NM. Magedov IV. Kireev AS. Kornienko A. Org. Lett.  2006,  8:  899 
    Google Scholar
24

Structural parameters for 4f: data collection: Rigaku Mercury CCD area detector; C25H16N4, yellow solid, crystal dimension 0.55 × 0.35 × 0.30 mm, triclinic, space group P 1, a = 9.7744 (16) Å, b = 9.7927 (11) Å, c = 11.233 (2) Å, α = 73.121 (13)˚, β = 86.008 (16)˚, γ = 63.853 (10)˚, V = 921.5 (2) ų, Mr = 372.42, Z = 2, Dc = 1.171 Mg/m³, λ (Mo-Kα) = 0.71070 Å, µ = 0.082 mm- ¹, F(000) = 388, 3.10˚ < θ < 25.34˚, R I >2 σ ( I ) = 0.0544, wR I >2 σ ( I ) = 0.1159, largest diff. peak and hole: 0.158 and -0.205 e Å-³. CCDC reference number 684602.

25

Structural parameters for 5b: data collection: Rigaku Mercury CCD area detector; C25H17BrN4, colorless solid, crystal dimension 0.27 × 0.20 × 0.16 mm, triclinic, space group P 1, a = 11.286 (2) Å, b = 13.516 (2) Å, c = 14.423 (3) Å, α = 90.685 (2)˚, β = 108.077 (3)˚, γ = 102.674 (3)˚, V = 2032.9 (6) ų, Mr = 452.33, Z = 4, Dc = 1.478 Mg/m³, λ (Mo-Kα) = 0.71075 Å, µ = 2.042 mm- ¹, F(000) = 916, 3.10˚ < θ < 25.50˚, R I >2 σ ( I ) = 0.0586, wR I >2 σ ( I ) = 0.1540, largest diff. peak and hole: 2.424 and -0.662 e Å-³. CCDC reference number 713488.