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Synthesis 2009(16): 2725-2728  
DOI: 10.1055/s-0029-1216878
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Microwave-Assisted Silver(I)-Mediated Selective O-Alkylation of Aromatic Imidate Systems

Brajendra K. Singha,b, Claudia Cavalluzzoa, Marc De Maeyerc, Zeger Debyserd, Virinder S. Parmarb, Erik Van der Eycken*a
a Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Katholieke Universiteit Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium
Fax: +3216327990; e-Mail: erik.vandereycken@chem.kuleuven.be;
b Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
c Laboratory for Biomolecular Modelling, Katholieke Universiteit Leuven, Celestijnenlaan 200G, 3001 Leuven, Belgium
d Molecular Medicine, Katholieke Universiteit Leuven, Kapucijnenvoer 33, 3000 Leuven, Belgium
Further Information

Publication History

Received 8 April 2009
Publication Date:
26 June 2009 (online)

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Abstract

A novel microwave-assisted protocol has been developed for the selective O-alkylation of aromatic imidate systems with various halides under microwave irradiation using silver carbonate as the base. Products were obtained in short reaction time and in excellent yields.

Key words

O-alkylation - silver carbonate - microwave - 2-pyridones - 2-(1H)-pyrazinones

    References

  • 1a Youngdale GA. Oglia TF. J. Med. Chem.  1985,  28:  1790 
    Google Scholar
  • 1b Evans DA. Dinsmore CJ. Watson PS. Wood MR. Richardson TI. Trotter BW. Katz JL. Angew. Chem. Int. Ed.  1998,  37:  2704 ; Angew. Chem. 1998, 110, 2868
    Google Scholar
  • 1c Nicolaou KC. Natarajan S. Li H. Jain NF. Hughes R. Solomon ME. Ramanjulu JM. Boddy CNC. Takayanagi M. Angew. Chem. Int. Ed.  1998,  37:  2708 ; Angew. Chem. 1998, 110, 2872
    Google Scholar
  • 1d Baldwin JE. Adlington RM. Conte A. Irlapati NR. Marquez R. Pritchard GJ. Org. Lett.  2002,  4:  2125 
    Google Scholar
  • 1e Deng H. Jung J.-K. Liu T. Kuntz KW. Snapper ML. Hoveyda AH. J. Am. Chem. Soc.  2003,  125:  9032 
    Google Scholar
  • 1f Wei ZL. Petukhov PA. Xiao Y. Tuckmantel W. George C. Kellar KJ. Kozikowski AP. J. Med. Chem.  2003,  46:  921 
    Google Scholar
  • 1g Freeman GA. Webster-Andrews C. Hopkins AL. Lowell GS. Schaller LT. Cowan JR. Gonzáles SS. Koszalka GW. Hazen RJ. Boone LR. Ferris RG. Creech KL. Roberts GB. Short SA. Weaver K. Reynolds DJ. Milton J. Ren J. Stuart DI. Stammers DK. Chan JH. J. Med. Chem.  2004,  47:  5923 
    Google Scholar
  • For reviews, see:
  • 2a Nicolaou KC. Boddy CNC. Brase S. Winssinger N. Angew. Chem. Int. Ed.  1999,  38:  2096 ; Angew. Chem. 1999, 111, 2230
    Google Scholar
  • 2b Blankenstein J. Zhu J. Eur. J. Org. Chem.  2005,  1949 
    Google Scholar
  • 2c Frlan R. Kikelj D. Synthesis  2006,  2271 
    Google Scholar
  • For examples of Ag2CO3 as base, see:
  • 3a Kornblum N. Smiley RA. Blackwood RK. Iffand DC. J. Am. Chem. Soc.  1955,  77:  6269 
    Google Scholar
  • 3b Kornblum N. Berrigan PJ. LeNoble WJ. J. Am. Chem. Soc.  1963,  85:  1141 
    Google Scholar
  • 3c Kornblum N. Seltzer R. Haberfield P. J. Am. Chem. Soc.  1963,  85:  1148 
    Google Scholar
  • 3d Hopkins GC. Jonak JP. Minnemeyer HJ. Tieckelmann H. J. Org. Chem.  1966,  31:  3969 
    Google Scholar
  • 3e Hopkins GC. Jonak JP. Minnemeyer HJ. Tieckelmann H. J. Org. Chem.  1967,  32:  4040 
    Google Scholar
  • 3f

    Ref. 1d-f.

    Google Scholar
  • 3g Morel AF. Larghi EL. Selvero MM. Synlett  2005,  2755 
    Google Scholar
  • 3h For AgOAc as base, see: Peukert F. Schwahn U. Güssregen S. Schreuder H. Hofmeister A. Synthesis  2005,  1550 
    Google Scholar
  • 3i Tomchin AB. Shirokii GA. Dmitrukha VS. Khim. Geterotsikl. Soedin.  1976,  83 ; Chem. Abstr. 1976, 84, 179383m
    Google Scholar
  • 3j For Ag2O as base, see: Da Silva JFM. Garden SJ. Pinto AC. J. Braz. Chem. Soc.  2001,  12:  273 
    Google Scholar
  • 3k

    Ref. 1a,g.

    Google Scholar
  • 4a Bernstein PR, Shaw A, Thomas RM, Veale CA, Warner P, and Wolanin EJ. inventors; PCT Int. Appl. 1993; WO  9321209.  Chem. Abstr. 1994, 121, 301319
  • 4b Warner P. Green RC. Gomes B. Strimpler AM. J. Med. Chem.  1994,  37:  3090 
    Google Scholar
  • 4c Damewood JR. Edwards PD. Feeney S. Gomes BC. Steelman GB. Tuthill PA. Williams JC. Warner P. Woolson SA. Wolanin DJ. Veale CA. J. Med. Chem.  1994,  37:  3303 
    Google Scholar
  • 4d Bernstein PR. Andisik DW. Bradley PK. Bryant CB. Ceccarelli C. Damewood JR. Earley RA. Edwards PD. Feeney S. Gomes BC. Kosmider BJ. Steelman GB. Thomas RM. Vacek EP. Veale CA. Williams JC. Wolanin DJ. Woolson SA. J. Med. Chem.  1994,  37:  3313 
    Google Scholar
  • 4e Brown FJ. Andisik DW. Bernstein PR. Bryant CB. Ceccarelli C. Damewood JR. Edwards PD. Earley RA. Feeney S. Green RC. Gomes B. Kosmider BJ. Krell RD. Shaw A. Steelman GB. Thomas RM. Vacek EP. Veale CA. Tuthill PA. Warner P. Williams JC. Wolanin DJ. Woolson SA. J. Med. Chem.  1994,  37:  1259 
    Google Scholar
  • 4f Veale CA. Bernstein PR. Bryant C. Ceccarelli C. Damewood JR. Earley R. Feeney SW. Gomes B. Kosmider BJ. Steelman GB. Thomas RM. Vacek EP. Williams JC. Wolanin DJ. Woolson S. J. Med. Chem.  1995,  38:  98 
    Google Scholar
  • 5a Semple G. Ashworth DM. Baker GR. Batt AR. Baxter AJ. M. Benzies DW. Elliot LH. Evans DM. Franklin RJ. Hudson P. Jenkins PD. Pitt GR. Rooker DP. Sheppard A. Szelke M. Yamamoto S. Isomura Y. Bioorg. Med. Chem. Lett.  1997,  7:  1337 
    Google Scholar
  • 5b Semple G. Ashworth DM. Batt AR. Baxter AJ. M. Benzies DW. Elliot LH. Evans DM. Franklin RJ. Hudson P. Jenkins PD. Pitt GR. Rooker DP. Yamamoto S. Isomura Y. Bioorg. Med. Chem. Lett.  1998,  8:  959 
    Google Scholar
  • 6a Sanderson PE. Dyer DL. Naylor-Olsen AN. Vacca JP. Gardell SJ. Lewis SD. Lucas BJ. Lyle EA. Lynch JJ. Mulichak AM. Bioorg. Med. Chem. Lett.  1997,  7:  1497 
    Google Scholar
  • 6b Verissimo E. Berry N. Gibbson P. Cristiano MLS. Rosenthal PJ. Gut J. Ward SA. O’Neill PM. Bioorg. Med. Chem. Lett.  2008,  18:  4210 
    Google Scholar
  • 7a Sanderson PE. Cutrona KJ. Dorsey BD. Dyer DL. McDonough CM. Naylor-Olsen AN. Chen I.-W. Chen Z. Cook JJ. Gardell SJ. Krueger JA. Lewis SD. Lin JH. Lucas BJ. Lyle EA. Lynch JJ. Stranieri MT. Vastag K. Shafer JA. Vacca JP. Bioorg. Med. Chem. Lett.  1998,  8:  817 
    Google Scholar
  • 7b Reiner JE. Lim-Wilby MS. Brunck TK. Ha-Uong T. Goldman EA. Abelman MA. Nutt RF. Semple JE. Tamura SY. Bioorg. Med. Chem. Lett.  1999,  9:  895 
    Google Scholar
  • 8 Saraogi I. Incarvito CD. Hamilton AD. Angew. Chem. Int. Ed.  2008,  47:  9691 ; Angew. Chem. 2008, 120, 9721
    CrossrefGoogle Scholar
  • 9 Reutov OA. Beletskaya IP. Kurts AL. Ambident Anions   Plenum; New York: 1983. 
    Google Scholar
  • 10a de la Hoz A. Tetrahedron  2008,  64:  8169 
    Google Scholar
  • 10b Almena I. Diaz-Ortiz A. Diez-Barra E. de la Hoz A. Loupy A. Chem. Lett.  1996,  333 
    Google Scholar
  • 11 Morel AF. Larghi EL. Selvero MM. Synlett  2005,  2755 
    Article in Thieme ConnectGoogle Scholar
  • 12 Appukkuttan P. Van der Eycken E. Eur. J. Org. Chem.  2008,  1133 
    CrossrefGoogle Scholar
  • 13 Ernst JT. Becerril J. Park HS. Yin H. Hamilton AD. Angew. Chem. Int. Ed.  2003,  42:  535 ; Angew. Chem. 2003, 115, 553
    CrossrefGoogle Scholar
  • 14 Kaval N. Appukkuttan P. Van der Eycken E. The Chemistry of 2(1H)-Pyrazinones in Solution and on Solid Support in Microwave-Assisted Synthesis of Heterocycles, In Topics in Heterocyclic Chemistry   Vol. 1:  Van der Eycken E. Kappe CO. Springer Verlag; Berlin: 2006.  p.267-304  
    Google Scholar
  • 15a Rombouts FJR. De Borggraeve WM. Delaere D. Froeyen M. Toppet SM. Compernolle F. Hoornaert GJ. Eur. J. Org. Chem.  2003,  1868 
    Google Scholar
  • 15b Pawar VG. De Borggraeve WM. Synthesis  2006,  2799 
    Google Scholar