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Synthesis 2009(10): 1615-1622  
DOI: 10.1055/s-0028-1088051
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Synthesis of 5H-Thiazolo[3,2-a]pyrimidin-5-ones from Morita-Baylis-Hillman Adduct Acetates under Solvent-Free and Base-Free Conditions

Weihui Zhong, Baoming Guo, Fuliang Lin, Yongliang Liu, Weike Su*
Key Laboratory of Pharmaceutical Engineering of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
Fax: +86(571)88320752; e-Mail: suweike@zjut.edu.cn;
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Publikationsverlauf

Received 2 December 2008
Publikationsdatum:
20. April 2009 (online)

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Abstract

5H-Thiazolo[3,2-a]pyrimidin-5-ones were easily prepared in good to excellent yields with high regioselectivity by nucleophilic addition of thiazol-2-amines to Morita-Baylis-Hillman adduct acetates, followed by cyclization and a thermo-sigmatropic shift procedure under solvent-free and base-free conditions.

Key words

fused-ring systems - heterocycles - α,β-unsaturated esters - thiazol-2-amines - solvent-free - base-free

    References

  • 1a Sharma VP. Indian J. Heterocycl. Chem.  2004,  14:  35 
    Google Scholar
  • 1b Meinhardt G. Eppinger E. Schmidmaier R. Anti-Cancer Drugs  2002,  13:  725 
    Google Scholar
  • 1c Jones DE, Coates JAV, Rhodes DI, Deadman JJ, Vandegrafe NA, Winfield LJ, Thienthong N, Issa W, Choi N, and Macfarlane K. inventors; WO Patent  77188.  ; Chem. Abstr. 2008, 149, 128851
  • 1d Brough PA, Cheetham SC, Kerrigan F, and Watts JP. inventors; WO Patent  71549.  ; Chem. Abstr. 2000, 134, 29416
  • 1e Yadav RK. Mishra AR. Wahab A. Mishra RM. Indian J. Heterocycl. Chem.  2007,  16:  305 
    Google Scholar
  • 1f Mohan J. Kumar A. Indian J. Heterocycl. Chem.  2002,  11:  325 
    Google Scholar
  • 2 Kennis LEJ, Vandenberk J, and Mertens JC. inventors; EP  110435.  ; Chem. Abstr. 1984, 102, 6522
  • 3a Novellino E. Cosimelli B. Ehlardo M. Greco G. Iadanza M. Lavecchia A. Rimoli MG. Sala A. Settimo AD. Primofiore G. Settimo FD. Taliani S. Motta CL. Klotz K. Tuscano D. Trincavelli ML. Martini C. J. Med. Chem.  2005,  48:  8253 
    Google Scholar
  • 3b Huang X. Liu Z. J. Org. Chem.  2002,  67:  6731 
    Google Scholar
  • 3c Landreau C. Deniaud D. Meslin JC. J. Org. Chem.  2003,  68:  4912 
    Google Scholar
  • 3d Bibas H. Moloney DWJ. Neumann R. Shtaiwi M. Bernhardt PV. Wentrup C. J. Org. Chem.  2002,  67:  2619 
    Google Scholar
  • 3e Erian AW. Sherifa SM. Mohamed NR. ARKIVOC  2001,  (x):  85 
    Google Scholar
  • 3f Abdel-Hafez SH. Phosphorus, Sulfur Silicon Relat. Elem.  2003,  178:  2563 
    Google Scholar
  • 3g Toche RB. Ghotekar BK. Kazi MA. Kendre DB. Jachak MN. Tetrahedron  2007,  63:  8157 
    Google Scholar
  • 3h Jakše R. Svete J. Stanovnik B. Golobič A. Tetrahedron  2004,  60:  4601 
    Google Scholar
  • 4a Basavaiah D. Rao KV. Reddy RJ. Chem. Soc. Rev.  2007,  36:  1581 
    Google Scholar
  • 4b Basavaiah D. Rao AJ. Satyanarayana T. Chem. Rev.  2003,  103:  811 
    Google Scholar
  • 4c Basavaiah D. Rao PD. Hyma RS. Tetrahedron  1996,  52:  8001 
    Google Scholar
  • 4d Drewes SE. Roos GHP. Tetrahedron  1988,  44:  4653 
    Google Scholar
  • 5a Lee HS. Kim JM. Kim JN. Tetrahedron Lett.  2007,  48:  4119 
    Google Scholar
  • 5b Kim SJ. Lee HS. Kim JN. Tetrahedron Lett.  2007,  48:  1069 
    Google Scholar
  • 5c Kabalka GW. Venkataiah B. Dong G. J. Org. Chem.  2004,  69:  5807 
    Google Scholar
  • 5d Gong JH. Kim HR. Ryu HR. Kim YN. Bull. Korean Chem. Soc.  2002,  23:  789 
    Google Scholar
  • 5e Im YJ. Na JE. Kim JN. Bull. Korean Chem. Soc.  2003,  24:  511 
    Google Scholar
  • 5f Basavaiah D. Reddy RJ. Org. Biomol. Chem.  2008,  6:  1034 
    Google Scholar
  • 5g Singh V. Batra S. Tetrahedron  2008,  64:  4511 
    Google Scholar
  • 6a Zhong W. Zhao Y. Su W. Tetrahedron  2008,  64:  5491 
    Google Scholar
  • 6b Zhong W. Lin F. Chen R. Su W. Synthesis  2008,  2561 
    Google Scholar
  • 6c Zhong W. Zhao Y. Guo B. Su W. Synth. Commun.  2008,  38:  3291 
    Google Scholar
  • 7a Clark JH. Green Chem.  2006,  8:  17 
    Google Scholar
  • 7b Sheldon RA. Green Chem.  2008,  10:  359 
    Google Scholar
  • 7c Maddessa ML. Kilbinger AFM. Chem. Commun.  2007,  31:  3231 
    Google Scholar
  • 7d Mosrin M. Boudet N. Knochel P. Org. Biomol. Chem.  2008,  6:  3237 
    Google Scholar
  • For the preparation of thiazol-2-amines, see:
  • 10a Furruiss BS. Hannaford AJ. Smith PWG. Tatchell AR. Vogel’s Textbook of Practical Organic Chemistry   5th ed., Vol. 2:  Elsevier; Amsterdam: 1989.  p.1152 
    Google Scholar
  • 10b Allen CFH. VanAllan J. Org. Synth.  1955,  3:  76 
    Google Scholar