117157-62-7Relevant articles and documents
C-H Functionalization of Benzothiazoles via Thiazol-2-yl-phosphonium Intermediates
Sch?mberg, Fritz,Vilotijevic, Ivan,Wagner, Konrad,Zi, You
supporting information, (2020/05/05)
Benzothiazoles undergo regioselective C2-H functionalization with triphenylphosphine to form thiazol-2-yl-triphenylphosphonium salts, and these phosphonium salts react with a wide range of O- A nd N-centered nucleophiles to give the corresponding ethers, amines, and C-N biaryls. The reactions proceed under mild conditions and allow for the recovery of triphenylphosphine at the end of the sequence. In the presence of hydroxide, phosphonium salts undergo disproportionation, resulting in the reduction of the benzothiazole, which is useful for specific C2 deuteration of benzothiazoles.
Convenient and reliable routes towards 2-aminothiazoles: Palladium-catalyzed versus copper-catalyzed aminations of halothiazoles
Toulot, Stephanie,Heinrich, Timo,Leroux, Frederic R.
supporting information, p. 3263 - 3272 (2013/12/04)
Two efficient methods for the amination of 2-halothiazoles are presented here. A first protocol requires a Pd/L system. Several 2-aminothiazoles were synthesized under optimized conditions and isolated in good yields. The first palladium-catalyzed C-N coupling reactions between 2-halothiazoles and primary alkylamines are presented. In a second part, ligand-free copper-catalyzed aminations of 2-halothiazoles by alkylamines and aniline in a green solvent have been developed. The protocol is very effective for primary and secondary amines and perfectly tolerates the presence of another halide moiety on the 2-halothiazole. The reaction occurs under the assistance of microwave irradiation, which drastically decreases the reaction time. The reaction leads to the formation of 2-aminothiazoles, key molecules in pharmaceutical research. Copyright
Direct, metal-free amination of heterocyclic amides/ureas with NH-heterocycles and N-substituted anilines in POCl3
Deng, Xiaohu,Roessler, Armin,Brdar, Ivana,Faessler, Roger,Wu, Jiejun,Sales, Zachary S.,Mani, Neelakandha S.
experimental part, p. 8262 - 8269 (2011/12/04)
A POCl3-mediated, direct amination reaction of heterocyclic amides/ureas with NH-heterocycles or N-substituted anilines is described. Compared to the existing methods, this operationally simple protocol provides unique reactivity and functional