Elsevier

Tetrahedron Letters

Volume 42, Issue 27, 2 July 2001, Pages 4495-4497
Tetrahedron Letters

Towards the synthesis of C-glycosylated dihydropyrimidine libraries via the three-component Biginelli reaction. A novel approach to artificial nucleosides

https://doi.org/10.1016/S0040-4039(01)00769-9Get rights and content

Abstract

The Lewis acid catalyzed (BF3·Et2O, CuCl, AcOH) one-pot three-component cyclocondensation of urea with C-glycosylated aldehydes and β-keto esters (Biginelli reaction) in a combinatorial manner afforded three different series of 3,4-dihydropyrimidin-2(1H)-ones bearing C-glycosyl moieties at C4, C6, and at both C4 and C6.

Section snippets

Acknowledgments

We gratefully thank the University of Ferrara for financial support.

References (17)

  • C.O Kappe

    Bioorg. Med. Chem. Lett.

    (2000)
    C.O Kappe et al.

    Heterocycles

    (1999)
    A.I McDonald et al.

    J. Org. Chem.

    (1999)
  • For a recent review, see: Kappe, C. O. Acc. Chem. Res. 2000, 33,...
  • B.C Ranu et al.

    J. Org. Chem.

    (2000)
    Y Ma et al.

    J. Org. Chem.

    (2000)
    E.H Hu et al.

    J. Org. Chem.

    (1998)
  • A Stadler et al.

    J. Chem. Soc., Perkin Trans. 2

    (2000)
  • For an updated list of leading references on this topic, see: Jauk, B.; Belaj, F.; Kappe, C. O. J. Chem. Soc., Perkin...
  • (a)Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland, S.; Hedberg, A.; O'Reilly, B. C. J. Med. Chem....K.S Atwal et al.

    J. Med. Chem.

    (1990)
  • We are aware of a few reports dealing with the use of rather simple sugar aldehydes...
  • A Dondoni

    Pure Appl. Chem.

    (2000)
    A Dondoni et al.

    J. Org. Chem.

    (1994)
There are more references available in the full text version of this article.

Cited by (41)

View all citing articles on Scopus
View full text