title: New methods for the synthesis of 2-aminothiazolones.
abstract: 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.
authors.affiliation: Chemical Process R&D, Amgen Inc., One Amgen Center Drive, Thousand Oaks, California 91320, USA. scaille@amgen.com
authors.forename: Seb
authors.initials: S
authors.lastname: Caille
authors.forename: Eric A
authors.initials: EA
authors.lastname: Bercot
authors.forename: Sheng
authors.initials: S
authors.lastname: Cui
authors.forename: Margaret M
authors.initials: MM
authors.lastname: Faul
mesh_terms: D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D013844:Thiazoles / Q000138:chemical synthesis*
chemical_list: D013844:Thiazoles; C004483:2-aminothiazole