3755-83-7Relevant academic research and scientific papers
Exploration and Optimization of an Efficient One-pot Sequential Synthesis of Di/tri-substituted Thiazoles from α-Bromoketones, Thioacids Salt, and Ammonium Acetate
Venkateswararao, Eeda,Jalani, Hitesh B.,Manoj,, Manickam,Jung, Sang-Hun
, p. 1449 - 1456 (2016/09/24)
Exploration of scope of an optimized one-pot sequential procedure for preparing of 2,4-di- and 2,4,5-tri-substituted thiazoles has been accomplished. The synthesis was performed by the initial formation of a β-keto-thioester intermediate from nucleophilic substitution of α-bromoketones with thioacid potassium salts, followed by treatment with ammonium acetate and one equivalent of acetic acid in toluene to form imine intermediate eventually leading to cyclization yielding thiazoles. This procedure should be highlighted with a flexible way to control the substitution pattern around thiazole ring by choosing appropriately substituted α-bromoketones even containing acid labile functionality and thioacid potassium salts, and thus its applicability is very wide.
Catalytic transformation of esters of 1,2-azido alcohols into α-amido ketones
Kim, Yongjin,Pak, Han Kyu,Rhee, Young Ho,Park, Jaiwook
supporting information, p. 6549 - 6552 (2016/06/01)
The esters of 1,2-azido alcohols were transformed into α-amido ketones without external oxidants through the Ru-catalyzed formation of N-H imines with the liberation of N2 followed by intramolecular migration of the acyl moiety. A wide range of α-amido ketones were obtained, and one-pot transformation into the corresponding oxazoles (or a thiazole) was demonstrated.
Direct arylation of imidazo[2,1-b]thiazoles and thiazoles with aryl iodides via CuCl2/PPh3-catalyzed C-H bond functionalization
Ma, Yuchang,Na, Min,Gu, Yanfang,Huang, Guoli,Li, Xia,Chen, Yegao
, p. 165 - 169 (2015/03/30)
With PPh3 acting as a ligand, a convenient method for CuCl2-catalyzed arylation of imidazo[1,2-b]thiazoles and thiazoles with aryl iodides under mild reaction conditions is described. Preliminary mechanistic studies of this arylation involving a formal Cu(I) to Cu(0) and Cu(II) route by convergent disproportionation of the copper mediator are also reported.
A simple route to new phenanthro- and phenanthroid-fused thiazoles by a PIFA-mediated (hetero)biaryl coupling reaction
Moreno, Isabel,Tellitu, Imanol,Dominguez, Esther,SanMartin, Raul
, p. 2126 - 2135 (2007/10/03)
An application of the PIFA-mediated [PIFA: phenyliodine(III) bis(trifluoroacetate) biaryl coupling reaction is presented and extended to the formation of heterobiaryl connections. A preliminary study of the scope and limitations of this procedure was carried out in the synthesis of phenanthroids 11 from a series of phenethyl-substituted heterocycles 10, It was observed that in some cases a competitive dimerization process took place. It was also found that the coupling step could be efficiently extended to a larger number of examples if an aromatic ring were situated fused to the 1,2-diarylethane skeleton, as in 23 and 30. The synthesis of a series of 4,5-diarylthiazoles 23a-g was therefore carried out to explore the electronic requirements and the regioselectivity of the PIFA-mediated non-phenolic coupling reaction. When the same procedure was applied to aryl-heteroarylthiazoles 30, a series of phenanthroid-fused thiazoles 31 was obtained in good overall yields. To the best of our knowledge, no oxidative aryl-heteroaryl coupling reaction of this type had previously been reported. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
An efficient synthesis of phenanthro-fused thiazoles by a non-phenolic oxidative coupling procedure of 4,5-diarylthiazoles
Moreno,Tellitu,SanMartin,Badia,Carrillo,Dominguez
, p. 5067 - 5070 (2007/10/03)
A concise synthesis of the title compounds 6 is accomplished in high overall yield in a two step process starting from bromoketone 4. A thiazole ring formation and a non-phenolic oxidative coupling reaction using PIFA are features of the described synthesis. An exploration of the electronic requirements and the regioselectivity of the cyclization is also presented.
