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PubMed · 11148059

A novel solid-phase approach to 2,4-diaminothiazoles.

R Baer·T Masquelin
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Abstract

A novel solid-phase synthesis of a 2,4-diaminothiazole library starting from a polymer-bound thiouronium salt is described. The synthetic strategy involves formation of polymer-bound thioureido-thiourea intermediates [5] which by treatment with alpha-bromo-ketones [6] undergoes S-alkylation, followed by a base-catalyzed intramolecular-ring closure/cleavage to give 2,4-diaminothiazoles [8]. This strategy tolerates a wide range of functionality and protecting groups. The novel feature of our method is a polymer-supported auto-scavenging strategy (PSAS), which provides a clean, high-yielding, and traceless synthesis to 2,4-diaminothiazoles.

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AlkylationChromatography, High Pressure LiquidCombinatorial Chemistry TechniquesCyclizationSpectrophotometry, UltravioletThiazolesJournal Article

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R Baer, T Masquelin. A novel solid-phase approach to 2,4-diaminothiazoles.. https://doi.org/10.1021/cc000005s

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