Abstract
A new efficient synthesis of optically active bicyclic 2-pyridiones has been developed using microwave irradiation. The synthesis is a two-step procedure via Δ2-thiazolines, which only requires a 3 + 2 min reaction time compared to 2 days when using conventional heating. The optimized conditions proved to be suitable for the synthesis of a small library in excellent yields and with limited racemizations.
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Emtenas, H., Ahlin, K., Pinkner, J.S., Hultgren, S.J., and Almqvist, F., Design and parallel solid-phase synthesis of ringfused 2-pyridinones that target pilus biogenesis in pathogenic bacteria, J. Comb. Chem., 4 (2002) 630–639.
Emtenas, H., Alderin, L., and Almqvist, F., An enantioselective ketene-imine cycloaddition method for synthesis of substituted ring-fused 2-pyridinones, J. Org. Chem., 66 (2001) 6756–6761.
Svensson, A., Larsson, A., Emtenas, H., Hedenstrom, M., Fex, T., Hultgren, S.J., Pinkner, J.S., Almqvist, F., and Kihlberg, J., Design and evaluation of pilicides: Potential novel antibacterial agents directed against uropathogenic Escherichia coli, ChemBiochem, 2 (2001) 915–918.
Wipf, P., Synthetic Studies of Biologically Active Marine Cyclopeptides, Chem. Rev., 95 (1995) 2115–2134.
Wipf, P., Synthesis and structure-activity studies of lissoclinum peptide alkaloids, Alkaloids: Chemical and Biological Perspectives, 12 (1998) 187–228.
Einsiedel, J., Hubner, H., and Gmeiner, P., Benzamide bioisosteres incorporating dihydroheteroazole substructures: EPC synthesis and SAR leading to a selective dopamine D4 receptor partial agonist (FAUC 179), Bioorg. Med. Chem. Lett., 11 (2001) 2533–2536.
Zarantonello, P., Leslie, C.P., Ferritto, R., and Kazmierski, W.M., Total Synthesis and Semi-Synthetic Approaches to Analogues of Antibacterial Natural Product Althiomycin, Bioorg. Med. Chem. Lett., 12 (2002) 561–565.
Wipf, P., Reeves, J.T., Balachandran, R., and Day, B.W., Synthesis and Biological Evaluation of Structurally Highly Modi-fied Analogues of the Antimitotic Natural Product Curacin A, J. Med. Chem., 45 (2002) 1901–1917.
Lidstrom, P., Westman, J., and Lewis, A., Enhancement of combinatorial chemistry by microwave-assisted organic synthesis, Combinatorial Chemistry and High Throughput Screening, 5 (2002) 441–458.
Lidstrom, P., Tierney, J., Wathey, B., and Westman, J., Microwave assisted organic synthesis: a review, Tetrahedron, 57 (2001) 9225–9283.
Kappe, C.O., High-speed combinatorial synthesis utilizing microwave irradiation, Curr. Opin. Chem.Biol., 6 (2002) 314–320.
Ehrler, J. and Farooq, S., Total synthesis of thiangazole, Synlett, (1994) 702–704.
Meyers, A.I., Knaus, G., Kamata, K., and Ford, M.E., Asymmetric synthesis of R and S α-alkylalkanoic acids from metalation and alkylation of chiral 2-oxazolines, J. Am. Chem. Soc., 98 (1976) 567–576.
Meyers, A.I. and Whitten, C.E., Oxazolines. XXIV: Chiral oxazolines and thiazolines from L-serine and L-cysteine. Their potential use in asymmetric synthesis, Heterocycles, 4 (1976) 1687–1692.
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Emtenäs, H., Taflin, C. & Almqvist, F. Efficient microwave assisted synthesis of optically active bicyclic 2-pyridinones via Δ2-thiazolines. Mol Divers 7, 165–169 (2003). https://doi.org/10.1023/B:MODI.0000006800.46154.99
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DOI: https://doi.org/10.1023/B:MODI.0000006800.46154.99