A novel solid-phase approach to 2,4-diaminothiazoles.
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.
Baer
R
R
Department of Chemical Technologies, F. Hoffmann-La Roche AG, 4070 Basel, Switzerland.
Masquelin
T
T
D000478:Alkylation; D002851:Chromatography, High Pressure Liquid; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D013056:Spectrophotometry, Ultraviolet; D013844:Thiazoles / Q000138:chemical synthesis*
D013844:Thiazoles