PDF herunterladen
Synthesis 2009(16): 2802-2808  
DOI: 10.1055/s-0029-1216874
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

The First Mineral-Catalyzed One-Pot [3+1+2] Coupling Protocol for Multifunctionalized Fused-Ring Pyrimidines

Lal Dhar S. Yadav*, Ankita Rai
Green Synthesis Lab, Department of Chemistry, University of Allahabad, Allahabad 211002, India
Fax: +91(532)2460533; e-Mail: ldsyadav@hotmail.com;
Weitere Informationen

Publikationsverlauf

Received 14 April 2009
Publikationsdatum:
26. Juni 2009 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

This is the first report on montmorillonite K-10 clay (nanoclay)-catalyzed, domino reactions of unprotected d-glucose/d-xylose with amidines/guanidine and an activated natural amino acid 2-phenyl-1,3-oxazol-5-one. The procedure results in an efficient annulation of the iminosugar moiety with functionalized pyrimidines­ in excellent yields (79-92%) with high trans-diaste­reoselectivity (>94%). The reaction is effected under solvent-free microwave irradiation conditions via amidine/guanidine-driven coupling and ring-transformation reactions in a one-pot procedure.

Key words

carbohydrates - mineral-catalyzed - amidines/guanidine - microwaves - ring transformation - pyrimidines

    References

  • 1a Fleet GWJ. Karpas A. Dwek RA. Fellows LE. Tyms AS. Petursson S. Namgoong SK. Ramsden NG. Smith PW. Son JC. Wilson F. Witty DR. Jacob GS. Rademacher TW. FEBS Lett.  1998,  237:  128 
    Google Scholar
  • 1b Taylor DL. Sunkara P. Liu PS. Kang MS. Bowlin TL. Tyms AS. AIDS  1991,  5:  693 
    Google Scholar
  • 2a Nishimura Y. In Studies in Natural Products Chemistry   Vol. 16:  . Elsevier Science; B. V. Amsterdam: 1995.  p.75-121  
    Google Scholar
  • 2b Gross PE. Baker MA. Carver JP. Dennis JW. Clin. Cancer Res.  1995,  1:  935 
    Google Scholar
  • 3a Horii S. Fukase H. Matsuo T. Kameda Y. Asano N. Matsui K. J. Med. Chem.  1986,  29:  1038 
    Google Scholar
  • 3b Robinson KM. Begovic ME. Reinhart BL. Heineke EW. Ducep J.-B. Kastner PR. Marshall FN. Danzin C. Diabetes  1991,  40:  825 
    Google Scholar
  • 4 For a review, see: Asano N. Glycobiology  2003,  13:  93R 
    CrossrefPubMedGoogle Scholar
  • 5 Cipolla L. La Ferla B. Nicotra F. Curr. Top. Med. Chem.  2003,  3:  485 
    CrossrefGoogle Scholar
  • 6a Nash RJ. Watson AA. Asano N. In Alkaloids: Chemical and Biological Perspectives   Vol. 11:  Pelletier SW. Elsevier; Oxford: 1996.  p.345-376  
    Google Scholar
  • 6b Elbein AD. Molyneux RJ. In Comprehensive Natural Products   Vol. 3:  Barton D. Nakanishi K. Elsevier; New York: 1999.  p.129-160  
    Google Scholar
  • 7a Horii S. Fukase H. Mastsuo T. Kameda Y. Asano N. Mastusi K. Drugs Future  1986,  11:  1039 
    Google Scholar
  • 7b Horii S. Fukase H. Mastsuo T. Kameda Y. Asano N. Mastusi K. Drugs Future  1987,  12:  1157 
    Google Scholar
  • 8 Cesar J. J. Comb. Chem.  2005,  7:  517 
    CrossrefGoogle Scholar
  • 9a Hassan NA. Molecules  2000,  5:  827 ; and references cited therein
    Google Scholar
  • 9b Pemmsin M. Lnu-Due C. Hoguet F. Gaultier C. Narcisse J. Eur. J. Med. Chem.  1988,  23:  453 
    Google Scholar
  • 9c Cannito A. Pemmsin M. Lnu-Due C. Hoguet F. Gaultier C. Narcisse J. Eur. J. Med. Chem.  1990,  25:  635 
    Google Scholar
  • 9d Smith PAS. Kan RO. J. Org. Chem.  1964,  29:  2261 
    Google Scholar
  • 9e Nega S. Aionso J. Diazj A. Junquere F. J. Heterocycl. Chem.  1990,  27:  269 
    Google Scholar
  • 9f Tetsuo S. Mikio T. Hidetoshi H. Daijiro H. Akira I. Jpn. Kokai Tokyo Koho JP 62,132,884, 1987  Chem. Abstr. 1987,  107, 198350h 
    Google Scholar
  • 9g Chakaravorty PK, Grelnlee WJ, Dooseap K, Mantlo NB, and Patchett AA. inventors; A.P.C.T. Int. Appl.  WO9220687156.  ; Chem. Abstr. 1993, 118, 213104d
  • 9h Shishoo CJ. Jain KS. J. Heterocycl. Chem.  1992,  29:  883 
    Google Scholar
  • 9i Jauk B. Belaj F. Kappe CO. J. Chem. Soc., Perkin Trans. 1  1999,  307 
    Google Scholar
  • 10a Adlington RM. Baldwin JA. Catterick D. Pritchard GJ. J. Chem. Soc., Perkin Trans. 1  1999,  855 ; references cited therein
    Google Scholar
  • 10b Rosenthal GA. Plant Nonprotein Amino and Imino Acids Biological, Biochemical and Toxicological Properties   Academic Press; New York: NY, 1982.  p.117 
    Google Scholar
  • 10c Bell EA. Biochim. Biophys. Acta  1961,  47:  602 
    Google Scholar
  • 11a Brown DJ. In The Chemistry of Heterocyclic Compounds: The Pyrimidines   Vol. 16:  Weissberger A. Wiley-Interscience; New York: 1970. 
    Google Scholar
  • 11b Brown DJ. In Comprehensive Heterocyclic Chemistry   Vol. 3:  Katritzky AR. Rees CW. Pergamon Press; Oxford: 1984.  Chap. 2.13.
    Google Scholar
  • 11c Eicher T. Hauptmann S. Chemie der Heterocyclen   Georg Thieme Verlag; Stuttgart, New York: 1994.  p.398 
    Google Scholar
  • 11d Gilchrist TL. Heterocyclenchemie   Neunhoeffer H. Wiley-VCH; New York: 1995.  p.270 
    Google Scholar
  • 12a Lehn J.-M. Supramolecular Chemistry-Concepts and Perspectives   VCH; Weinheim: 1995.  Chap. 9.
    Google Scholar
  • 12b Hanan GS. Volkmer D. Schubert US. Lehn J.-M. Baum G. Fenske D. Angew. Chem. Int. Ed.  1997,  36:  1842 
    Google Scholar
  • 12c Semenov A. Spatz JP. Möller M. Lehn J.-M. Sell B. Schubert D. Weidl CH. Schubert US. Angew. Chem. Int. Ed.  1999,  38:  2547 
    Google Scholar
  • 13a Harriman A. Ziessel R. Coord. Chem. Rev.  1998,  171:  331 
    Google Scholar
  • 13b Harriman A. Ziessel R. Chem. Commun.  1996,  1707 
    Google Scholar
  • 14a Taylor EC. Knoff RJ. Meyer RF. Holmes A. Hoefle ML. J. Am. Chem. Soc.  1960,  82:  5711 
    Google Scholar
  • 14b Inoue S. Saggiomo AJ. Nodiff EA. J. Org. Chem.  1961,  26:  4504 
    Google Scholar
  • 14c Bredereck H. Effenberger F. Botsch H. Rehn H. Chem. Ber.  1965,  98:  1081 
    Google Scholar
  • 14d Chauhan SMS. Junjappa H. Synthesis  1974,  880 
    Google Scholar
  • 14e Kreutzberger A. Tesch U.-H. Chem. Ber.  1976,  109:  3255 
    Google Scholar
  • 14f Potts KT. Cipullo MJ. Ralli P. Theodoridis G. J. Org. Chem.  1983,  48:  4841 
    Google Scholar
  • 14g Kvita V. Synthesis  1986,  786 
    Google Scholar
  • 14h Schenone P. Sansebastiano L. Mosti L. J. Heterocycl. Chem.  1990,  27:  295 
    Google Scholar
  • 14i Papet A.-L. Marsura A. Synthesis  1993,  478 
    Google Scholar
  • 14j Yamanaka H. Takekawa T. Morita K. Ishihara T. Gupton JT. Tetrahedron Lett.  1996,  37:  1829 
    Google Scholar
  • 14k Wang T. Cloudsdale IS. Synth. Commun.  1997,  27:  2521 
    Google Scholar
  • 14l Ghosh U. Katzenellenbogen JA. J. Heterocycl. Chem.  2002,  39:  1101 
    Google Scholar
  • 15a Schmaker JM. Delia TJ. J. Org. Chem.  2001,  66:  7125 
    Google Scholar
  • 15b Turck A. Pré N. Lepretre-Gaquere A. Queguiner G. Heterocycles  1998,  49:  205 
    Google Scholar
  • 16 Eilingfeld H. Patsch M. Scheuermann H. Chem. Ber.  1968,  101:  2426 
    CrossrefGoogle Scholar
  • 17a Sing YL. Lee LF. J. Heterocycl. Chem.  1989,  26:  7 
    Google Scholar
  • 17b Alberola A. Andrês C. Ortega AG. Pedrosa R. Vicente M. Synth. Commun.  1987,  17:  1309 
    Google Scholar
  • 18a Guzmân A. Romero M. Talamâs FX. Villena R. Greenhouse R. Muchowski JM. J. Org. Chem.  1996,  61:  2470 
    Google Scholar
  • 18b Guzmân A. Romero M. Talamâs FX. Muchowski JM. Tetrahedron Lett.  1992,  24:  3449 
    Google Scholar
  • 19a Pourzal A.-A. Synthesis  1983,  717 
    Google Scholar
  • 19b Martínez AG. Fernandez AH. Alvarez RM. Losada MCS. Vilchez DM. Subramanian LR. Hanack M. Synthesis  1990,  881 
    Google Scholar
  • 19c Martînez AG. Fernândez AH. Fraile AG. Subramanian LR. Hanack M. J. Org. Chem.  1992,  57:  1627 
    Google Scholar
  • 19d Martînez AG. Fernândez AH. Âlvarez RM. Vilchez MDM. Gutiêrrez MLL. Subramanian LR. Tetrahedron  1999,  55:  4825 
    Google Scholar
  • 19e Ghosez L. Jnoff E. Bayard P. Sainte F. Beaudegnies R. Tetrahedron  1999,  55:  3387 
    Google Scholar
  • 20 Sakai N. Aoki Y. Sasada T. Konakahara T. Org. Lett.  2005,  7:  4705 
    CrossrefGoogle Scholar
  • 21 Yadav LDS. Awasthi C. Rai VK. Rai A. Tetrahedron Lett.  2008,  49:  2377 
    CrossrefGoogle Scholar
  • 22a Yadav LDS. Rai A. Rai VK. Awasthi C. Tetrahedron Lett.  2008,  49:  687 
    Google Scholar
  • 22b Yadav LDS. Awasthi C. Rai VK. Rai A. Tetrahedron Lett.  2007,  48:  8033 
    Google Scholar
  • 22c Yadav LDS. Rai VK. Tetrahedron  2007,  63:  6924 
    Google Scholar
  • 22d Yadav LDS. Rai VK. Tetrahedron Lett.  2006,  47:  395 
    Google Scholar
  • 22e Yadav LDS. Yadav S. Rai VK. Green Chem.  2006,  8:  455 
    Google Scholar
  • 22f Yadav LDS. Yadav S. Rai VK. Tetrahedron  2005,  61:  10013 
    Google Scholar
  • 23a Yadav LDS. Rai A. Rai VK. Awasthi C. Synlett  2007,  1905 
    Google Scholar
  • 23b Yadav LDS. Awasthi C. Rai VK. Rai A. Tetrahedron Lett.  2007,  48:  4899 
    Google Scholar
  • 24 Renewable Bioresources: Scope and Modification for Non-Food Applications   Stevens CV. Verhé RG. John Wiley and Sons; Chichester: 2004. 
    Google Scholar
  • 25 Yadav LDS. Yadav S. Rai VK. Tetrahedron  2005,  61:  10013 
    CrossrefGoogle Scholar
  • 26 Nishio T. Konno Y. Ori M. Sakamoto M. Eur. J. Org. Chem.  2001,  3553 
    CrossrefGoogle Scholar
  • 27 Chiba T. Nakai T. Chem. Lett.  1987,  2187 
    CrossrefGoogle Scholar
  • 28 Liao M. Yao W. Wang J. Synthesis  2004,  2633 
    Artikel in Thieme ConnectGoogle Scholar
  • 29 Evans DA. Nelson JV. Vogel E. Taber TR. J. Am. Chem. Soc.  1981,  103:  3099 
    CrossrefGoogle Scholar
  • 30 Mukaiyama T. Iwasawa N. Chem. Lett.  1984,  753 
    CrossrefGoogle Scholar
  • 31 Yadav LDS. Rai VK. Yadav S. Tetrahedron  2006,  62:  5464 
    CrossrefGoogle Scholar