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Synthesis 2011(4): 635-641  
DOI: 10.1055/s-0030-1258405
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Thermal and Microwave-Assisted Rapid Syntheses of Substituted Imidazo[1,2-a]pyridines Under Solvent- and Catalyst-Free Conditions

Kaushik C. Chunavala, Girdhar Joshi, Eringathodi Suresh, Subbarayappa Adimurthy*
Central Salt and Marine Chemicals Research Institute (CSIR), G. B. Marg, Bhavnagar 364 002, Gujarat, India
Fax: +91(278)2567562; e-Mail: sadimurthy@yahoo.com;
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Publikationsverlauf

Received 15 November 2010
Publikationsdatum:
12. Januar 2011 (online)

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Erratum zu diesem Artikel:

Thermal and Microwave-Assisted Rapid Syntheses of Substituted Imidazo[1,2-a]pyridines Under Solvent- and Catalyst-Free ConditionsSynthesis 2011; 2011(08): 1319-1319
DOI: 10.1055/s-0030-1259984

Abstract

Thermal and microwave-assisted rapid syntheses of highly substituted imidazo[1,2-a]pyridine derivatives by reaction of aminopyridines and α-bromo-β-keto esters under solvent-free conditions are described. Reactions carried out under microwave irradiation give the highest yields of products in reaction times of less than two minutes.

Key words

aminopyridines - α-bromo-β-keto esters - imidazo[1,2-a]pyridines - microwave irradiation - solvent-free - thermal

    References

  • 1 For a general review on the chemistry of imidazopyridine derivatives, see: Couty F. Evano G. In Comprehensive Heterocyclic Chemistry III   Vol. 2:  Katritzky AR. Ramsden CA. Scriven EFV. Taylor RJK. Elsevier; Oxford: 2008.  p.409-499  
    Suche in Google Scholar
  • 2a Guillaumet G, Berteina-Raboin S, El Kazzouli S, Delagrange P, and Caignard DH. inventors;  WO2006027474.  ; Chem. Abstr. 2006, 144, 254132
  • 2b Song G. Zhang Y. Li X. Organometallics  2008,  27:  1936 
    Suche in Google Scholar
  • 2c Enguehard C. Fauvelle F. Debouzy J. Peinnequin A. Thery I. Dabouis V. Gueiffier A. Eur. J. Pharm. Sci.  2005,  24:  219 
    Suche in Google Scholar
  • 2d Gudmundsson KS. John BA. Org. Lett.  2003,  5:  1369 
    Suche in Google Scholar
  • 2e Hamdouchi C. Zhong B. Mendoza J. Collins E. Jaramillo C. Diego J. Robertson D. Spencer CD. Anderson BD. Watkins SA. Zhang F. Brooks HB. Bioorg. Med. Chem. Lett.  2005,  15:  1943 
    Suche in Google Scholar
  • 3a Elhakmoui A. Gueiffier A. Milhavet JC. Blache Y. Chapat PJ. Bioorg. Med. Chem. Lett.  1994,  4:  1937 
    Suche in Google Scholar
  • 3b Gueiffier A. Lhassani M. Elhakmoui A. Snoeck R. Andrei G. Chavignion O. Teulade JC. Kerbal A. Essassi M. Debouzy JC. Witurowo JP. Blache Y. Balzarini J. De Clercq E. Chapat JP. J. Med. Chem.  1996,  39:  2856 
    Suche in Google Scholar
  • 3c Lhassani M. Chavignion O. Chezal JM. Teulade JC. Chapat JP. Snoeck R. Andrei G. Balzarini J. De Clercq E. Gueiffier A. J. Med. Chem.  1999,  34:  271 
    Suche in Google Scholar
  • 3d Gudmundsson KS. Drach JC. Townsend LB. J. Org. Chem.  1997,  62:  3453 
    Suche in Google Scholar
  • 3e Pan S. Wang G. Shinazi RF. Zhao K. Tetrahedron Lett.  1998,  39:  2695 
    Suche in Google Scholar
  • 3f Hamdouchi C. de Blas J. del Prado M. Gruber J. Heinz BA. Vance L. J. Med. Chem.  1999,  42:  50 
    Suche in Google Scholar
  • 3g Gudmundsson KS. Williams JD. Drach JC. Townsend LB. J. Med. Chem.  2003,  46:  1449 
    Suche in Google Scholar
  • 4a Kaminski JJ. Doweyko AM. J. Med. Chem.  1999,  40:  427 
    Suche in Google Scholar
  • 4b Kaminski JJ. Puchalski C. Solomon DM. Rizvi RK. Conn DJ. Elliot AJ. Lovey RG. Guzik H. Chui PJS. Long JF. McPhail AT. J. Med. Chem.  1989,  32:  1686 
    Suche in Google Scholar
  • 5a Rival Y. Grassy G. Michael G. J. Med. Chem.  1992,  40:  1170 
    Suche in Google Scholar
  • 5b Rewankar GR. Matthews JR. Robins RK. J. Med. Chem.  1975,  18:  1253 
    Suche in Google Scholar
  • 5c Ismail MA. Arafa RK. Wenzler T. Brun R. Tanious FA. Wilson WD. Boykin DW. Bioorg. Med. Chem.  2008,  16:  683 
    Suche in Google Scholar
  • 5d Odell LR. Nilsson MT. Gising J. Lagerlund O. Muthas D. Nordqvist A. Karlen A. Larhed M. Bioorg. Med. Chem. Lett.  2009,  19:  4790 
    Suche in Google Scholar
  • 6a Beswick PJ, Campbell IB, and Naylor A. inventors;  WO9631509.  ; Chem. Abstr. 1997, 126, 8117j
  • 6b Abignente E. Acta Chim. Therap.  1991,  18:  1253 
    Suche in Google Scholar
  • 6c Gudmundsson KS. Johns BA. Bioorg. Med. Chem. Lett.  2007,  17:  2735 
    Suche in Google Scholar
  • 7a Tully WR. Gardner CR. Gillespie RJ. Westwood R. J. Med. Chem.  1991,  34:  2060 
    Suche in Google Scholar
  • 7b Trapani G. Franco M. Latrofa A. Ricciardi L. Carotti A. Serra M. Sanna E. Biggio G. Liso G. J. Med. Chem.  1999,  42:  3934 
    Suche in Google Scholar
  • 7c Trapani G. Franco M. Ricciardi L. Latrofa A. Genchi G. Sanna E. Tuveri F. Gagetti E. Biggio G. Liso G. J. Med. Chem.  1997,  40:  3109 
    Suche in Google Scholar
  • 8 Sanfilippo PJ. Urbanski M. Press JB. Dubinsky B. Moore JB. J. Med. Chem.  1991,  34:  2060 
    CrossrefSuche in Google Scholar
  • 9 Fuchs K, Romig M, Mendla K, Briem H, and Fechteler K. inventors;  WO0214313.  ; Chem. Abstr. 2002, 136, 183824r
  • 10 Zhuang Z.-P. Kung M.-P. Wilson A. Lee W.-C. Plössl K. Hou C. Holtzman DM. Kung HF. J. Med. Chem.  2003,  46:  237 
    CrossrefPubMedSuche in Google Scholar
  • 11a Abe Y. Kayakiri H. Satoh S. Inoue T. Sawada Y. Imai KH. J. Med. Chem.  1998,  41:  564 
    Suche in Google Scholar
  • 11b Holm KJ. Goa KL. Drugs  2000,  59:  865 
    Suche in Google Scholar
  • 12a El Kazzouli S. Berteina-Raboin S. Mouaddib A. Guillaumet G. Tetrahedron Lett.  2003,  44:  6265 
    Suche in Google Scholar
  • 12b El Kazzouli S. Berthaut A. Berteina-Raboin S. Mouaddib A. Guillaumet G. Lett. Org. Chem.  2005,  2:  184 
    Suche in Google Scholar
  • 12c Koubachi J. El Kazzouli S. Berteina-Raboin S. Mouaddib A. Guillaumet G. J. Org. Chem.  2007,  72:  7650 
    Suche in Google Scholar
  • 12d Kamal A. Devaiah V. Reddy KL. Rajendar R. Shetti V. Shankaraiah N. J. Comb. Chem.  2007,  9:  267 
    Suche in Google Scholar
  • 12e Herath A. Dahl R. Cosford NDP. Org. Lett.  2010,  12:  412 
    Suche in Google Scholar
  • 12f Patel HS. Linn JA. Drewry DH. Hillesheim DA. Zuercher WJ. Hokstra WJ. Tetrahedron Lett.  2003,  44:  4077 
    Suche in Google Scholar
  • 12g Montgomery JA. Secrist JA. In Comprehensive Heterocyclic Chemistry   Vol. 5:  Katritzky AR. Rees CW. Potts KT. Pergamon; Oxford: 1984.  p.607 
    Suche in Google Scholar
  • 13a Chernyak N. Gevorgyan V. Angew. Chem. Int. Ed.  2010,  49:  2743 
    Suche in Google Scholar
  • 13b Bakherad M. Nasr-Isfahani H. Keivanloo A. Doostmohammadi N. Tetrahedron Lett.  2008,  49:  3819 
    Suche in Google Scholar
  • 13c Bakherad M. Nasr-Isfahani H. Keivanloo A. Sang G. Tetrahedron Lett.  2008,  49:  6188 
    Suche in Google Scholar
  • 14a Davey DD. J. Org. Chem.  1987,  52:  1863 
    Suche in Google Scholar
  • 14b Galons H. Bergerat I. Farnoux CC. Miocque M. Synthesis  1982,  1103 
  • 14c Knolker HJ. Boese R. Hitzemann R. Chem. Ber.  1990,  123:  327 
    Suche in Google Scholar
  • 14d Liu P. Fang L. Lei X. Lin G. Tetrahedron Lett.  2010,  51:  4605 
    Suche in Google Scholar
  • 14e Andaloussi M. Moreau E. Chavignon O. Teulade JC. Tetrahedron Lett.  2007,  48:  8392 
    Suche in Google Scholar
  • 14f Yadav JS. Subba Reddy BV. Rao YG. Srinivas M. Narsaiah AV. Tetrahedron Lett.  2007,  48:  7717 
    Suche in Google Scholar
  • 14g Adib M. Sheibani E. Zhu L.-G. Mirzaei P. Tetrahedron Lett.  2008,  49:  5108 
    Suche in Google Scholar
  • 14h Kercher T. Rao C. Bencsik JR. Josey JA. J. Comb. Chem.  2007,  9:  1177 
    Suche in Google Scholar
  • 14i Varma RS. Kumar D. Tetrahedron Lett.  1999,  40:  7665 
    Suche in Google Scholar
  • 14j Katagiri N. Kato T. J. Heterocycl. Chem.  1984,  21:  407 
    Suche in Google Scholar
  • 14k Kondo T. Kotachi S. Ogino S. Watanabe Y. Chem. Lett.  1993,  1317 
  • 15a Varma RS. Pure Appl. Chem.  2001,  73:  193 
    Suche in Google Scholar
  • 15b Bora U. Saikia A. Boruah RC. Org. Lett.  2003,  5:  435 
    Suche in Google Scholar
  • 15c Vega JA. Vaquero JJ. Builla JA. Ezquerra J. Hamdouchi C. Tetrahedron  1999,  55:  2317 
    Suche in Google Scholar
  • 15d Dimauro EF. Kennedy JM. J. Org. Chem.  2007,  72:  1013 
    Suche in Google Scholar
  • 16 Adimurthy S. Malakar CC. Beifuss U. J. Org. Chem.  2009,  74:  5648 
    CrossrefSuche in Google Scholar
  • 18a Byth FK. Culshaw JD. Green S. Oakes SE. Thomas AP. Bioorg. Med. Chem.  2004,  14:  2245 
    Suche in Google Scholar
  • 18b Katritzky AR. Xu YJ. Tu H. J. Org. Chem.  2002,  68:  4935 
    Suche in Google Scholar
  • 18c Kiselyov AS. Tetrahedron Lett.  2006,  47:  2941 
    Suche in Google Scholar
17

X-ray crystal data for 5g: empirical formula: C17H16N2O2, formula weight: 280.32, T = 293(2) K, λ = 0.71073, crystal system: monoclinic, space group: P21/c, unit cell dimensions: a = 11.419(3) Å, b = 14.292(4) Å, c = 9.001(2) Å, β = 99.912(4)˚, V = 1447.1(6) ų, Z = 4, density (calcd) = 1.287 mg/m³, absorption coefficient: 0.086 mm-¹, F(000) = 592, crystal size: 0.32 × 0.21 × 12 mm, reflections collected: 7540, independent reflections: 2813, R ( int) = 0.0225, data/restraints/parameters: 2813/0/193, goodness-of-fit on F ² = 1.151, final R indices [I ≥ 2σ(I)], R1 = 0.0623, wR2 = 0.1392, R indices (all data): R1 = 0.0742, wR2 = 0.1456, largest diff. peak and hole: 0.204 and -0.219 eÅ-³. CCDC 793451 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.