New methods for the synthesis of 2-aminothiazolones.
Two new methods for the synthesis of 2-aminothiazolones from 2-(4-methoxybenzylthio)acetic acids are described. A single reagent and simple experimental conditions are used in the key tandem deprotection-cyclization process. In the first approach 2-aminothiazolones are directly accessed via cyclization of the corresponding N-acylisothioureas. The second complementary approach provides access to a variety of 2-thiomethylthiazolones via cyclization of N-acyldithioimidates. The product 2-thiomethylthiazolones are then efficiently converted to 2-aminothiazolones via amine displacement.
Caille
Seb
S
Chemical Process R&D, Amgen Inc., One Amgen Center Drive, Thousand Oaks, California 91320, USA. scaille@amgen.com
Bercot
Eric A
EA
Cui
Sheng
S
Faul
Margaret M
MM
D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D013844:Thiazoles / Q000138:chemical synthesis*
D013844:Thiazoles; C004483:2-aminothiazole