Abstract
Solid-phase dendrimer chemistry using a symmetrical 1→3C-branched isocyanate monomer was used to prepareradiation-grafted polymers with enhanced loading. Afterevaluation of the physical and chemical properties of thesenew high-loading supports, they were tested in the multipleparallel synthesis of hydantoins.
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Hydantoin C: 1 H NMR (400 MHz, CDCl3) ? 0.84 (t, J= 7.5 Hz, 3H), ? 3.02 (dd, J= 4.5, 14.6 Hz, 1H), ? 3.09 (dd, J= 4.5, 14.6 Hz, 1H), ? 3.36 (m, 2H), ? 3.90 (t, J= 4.5 Hz, 1H), ? 3.91 (d, J= 15.1 Hz, 1H), ? 5.08 (d, J= 15.1 Hz, 1H), ? 7.03–7.07 (m, 4H), ? 7.18–7.27 (m, 6H); MS (ES+) m/e 363.2 (5%) (M+H)+, 747.4 (100%) (2M+Na)+. Hydantoin M: 1 H NMR (400 MHz, CDCl3) ? 1.42 (d, J= 7.0, 3H), ? 3.81 (s, 6H), ? 4.23 (q, J= 7.0, 1H), ? 4.45 (d, J= 15.6 Hz, 1H), ? 4.71 (d, J= 15.6 Hz, 1H), ? 6.50 (t, J= 2.0 Hz, 1H), ? 6.59 (d, J= 2.0 Hz, 2H), ? 7.45–7.58 (m, 5H), ? 6.97–7.06 (m, 6H); MS (ES+) m/e 341.2 (80%) (M+H)+, 703.3 (80%) (2M+Na)+.
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Lebreton, S., Newcombe, N. & Bradley, M. Loading amplification of radiation grafted polymers (crowns and lanterns) and their application in the solid-phase synthesis of hydantoin libraries. Mol Divers 6, 19–26 (2003). https://doi.org/10.1023/A:1024867013184
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DOI: https://doi.org/10.1023/A:1024867013184