1061709-83-8Relevant articles and documents
Ugi reactions with ammonia offer rapid access to a wide range of 5-aminothiazole and oxazole derivatives
Thompson, Mark J.,Chen, Beining
experimental part, p. 7084 - 7093 (2010/01/06)
(Chemical Equation Presented) A series of Ugi reactions has been successfully performed using ammonia as the amine component, employing 2,2,2-trifluoroethanol as a non-nucleophilic solvent in order to suppress known side reactions. Utilizing concentrated aqueous ammonia as a convenient source, this approach offered a simple, one-step assembly of Ugi adducts suitable for elaboration into a variety of 5-aminoazole compounds through postcondensation modifications. Free or N-substituted 5-aminothiazoles and 5-(trifluoroacetamido) oxazoles were all prepared by this improved methodology. The scope of the synthetic route developed and application of the different products are discussed.
Versatile assembly of 5-aminothiazoles based on the Ugi four-component coupling
Thompson, Mark J.,Chen, Beining
, p. 5324 - 5327 (2008/12/22)
A flexible route to novel 5-aminothiazoles has been developed based on cyclisation of diamide adducts, prepared using the Ugi reaction, in the presence of Lawesson's reagent. The Walborsky reagent (1,1,3,3-tetramethylbutyl isocyanide) was used as the isonitrile component, facilitating subsequent deprotection of the N-alkyl group to yield free 5-aminothiazoles, which were prepared with a variety of substituents at the 2- and 4-positions.