Reactive imidazole intermediates: simplified synthetic approach to functional aliphatic cyclic carbonates

Literature Information

Publication Date 2014-08-13
DOI 10.1039/C4PY00911H
Impact Factor 5.582
Authors

Johan V. Olsson, Daniel Hult, Yanling Cai, Sandra García-Gallego, Michael Malkoch


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Abstract

Reactive imidazole intermediates based on AB2 and A3 monomers, i.e. bis(methylol) propionic acid (bis-MPA) and trimethylolpropane (TMP) have successfully been synthesized and isolated on a 100 gram scale via a facile synthetic protocol using 1,1′-carbonyldiimidazole (CDI) as a key reagent. The robustness of the imidazole intermediates as bench stable precursors enabled the synthesis of a library of functional cyclic carbonates bearing relevant functionalities including hydrophilic PEGs, bioactive cholesterol and clickable groups. A number of functional polycarbonates were obtained by ring-opening polymerization, and their relevance in biomedical applications was highlighted by their low cytotoxicity on human dermal fibroblasts (hDF).

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Polymer Chemistry

Polymer Chemistry
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