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. 2013 Jul 8;69(27-28):5744-5750.
doi: 10.1016/j.tet.2013.04.071.

Cationic dirhodium carboxylate-catalyzed synthesis of dihydropyrimidones from propargyl ureas

Affiliations

Cationic dirhodium carboxylate-catalyzed synthesis of dihydropyrimidones from propargyl ureas

Miao Yang et al. Tetrahedron. .

Abstract

Cationic Rh(II) complexes are able to catalyze the regioselective hydroamination of propargyl ureas in a 6-endo fashion. This transformation permits access to interesting substitution patterns of dihydropyrimidines which have found use as nucleotide exchange factor inhibitors.

Keywords: ARF 6; Rhodium catalysis; dihydropyrimidone; heterocycle; hydroamination.

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Figures

Figure 1
Figure 1
Dihydropyrimidone strategy.
Figure 2
Figure 2
Manipulation of the secin scaffold for increased solubility.

References

    1. Kappe CO. Eur J Med Chem. 2000;35:1043. - PubMed
    2. Singh K, Arora D, Singh K, Singh S. Mini-Rev Med Chem. 2009;9:95. - PubMed
    3. Kappe CO. Tetrahedron. 1993;49:6937.
    1. Mayer TU, Kapoor TM, Haggarty SJ, King RW, Schreiber SL, Mitchison TJ. Science. 1999;286:971. - PubMed
    2. Atwal KS, Swanson BN, Unger SE, Floyd DM, Moreland S, Hedberg A, O’Reilly BC. J Med Chem. 1991;34:806. - PubMed
    1. Biginelli P. Gazz Chim Ital. 1893;23:360.
    1. For excellent reviews see: Kappe CO. J Org Chem. 1997;62:7201.Kappe CO. Acc Chem Res. 2000;33:879.Wan JP, Liu Y. Synthesis. 2010;23:3943.

    1. For enantioselective variants see: Li N, Chen XH, Song J, Luo S-W, Fan W, Gong L-Z. J Am Chem Soc. 2009;131:15301.Gong LZ, Chen XH, Xu XY. Chem Eur J. 2007;13:8920.Huang Y, Yang F, Zhu C. J Am Chem Soc. 2005;127:16386.Lou S, Taoka BM, Ting A, Schaus SE. J Am Chem Soc. 2005;127:11256.Goss JM, Schaus SE. J Org Chem. 2008;73:7651.Chen XH, Xu XY, Liu H, Cun LF, Gong LZ. J Am Chem Soc. 2006;128:14802.

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