103441-80-1Relevant academic research and scientific papers
Novel and efficient transformation of enamides into α-acyloxy ketones via an acyl intramolecular migration process
Zhou, Xiaoqiang,Ma, Haojie,Cao, Jinhui,Liu, Xingxing,Huang, Guosheng
supporting information, p. 10070 - 10073 (2016/11/06)
Hydrogen peroxide and anhydride mediated transformation of enamides to afford substituted α-acyloxy ketones is described. This transition-metal-free cascade reaction has a broad substrate scope and high efficiency. The acyl intramolecular migration procedure successfully achieved this acyloxylation process under mild conditions and increased the atom efficiency.
Structure-activity relationships of 2-aminothiazoles effective against Mycobacterium tuberculosis
Meissner, Anja,Boshoff, Helena I.,Vasan, Mahalakshmi,Duckworth, Benjamin P.,Barry III, Clifton E.,Aldrich, Courtney C.
, p. 6385 - 6397 (2013/10/22)
A series of 2-aminothiazoles was synthesized based on a HTS scaffold from a whole-cell screen against Mycobacterium tuberculosis (Mtb). The SAR shows the central thiazole moiety and the 2-pyridyl moiety at C-4 of the thiazole are intolerant to modification. However, the N-2 position of the aminothiazole exhibits high flexibility and we successfully improved the antitubercular activity of the initial hit by more than 128-fold through introduction of substituted benzoyl groups at this position. N-(3-Chlorobenzoyl)-4-(2-pyridinyl) -1,3-thiazol-2-amine (55) emerged as one of the most promising analogues with a MIC of 0.024 μM or 0.008 μg/mL in 7H9 media and therapeutic index of nearly ～300. However, 55 is rapidly metabolized by human liver microsomes (t1/2 = 28 min) with metabolism occurring at the invariant aminothiazole moiety and Mtb develops spontaneous low-level resistance with a frequency of ～10-5.
REACTIONS OF 2-ACYLPYRIDINE 1-OXIDES WITH ACID ANHYDRIDES
Nagano, Hiroyuki,Hamana, Masatomo
, p. 3249 - 3257 (2007/10/02)
Treatment of 2-acetyl- and 2-propionyl-pyridine 1-oxides (1a and 1b) with hot acetic, propionic and benzoic anhydrides initially gives the respective enol acylates (A), which further undergo deoxygenative β-acyloxylation to give enediol diacylates (E) and
Hypervalent Iodine Oxidation of Silyl Enol Ethers. A Direct Route to α-Hydroxy Ketones
Moriarty, Robert M.,Duncan, Michael P.,Prakash, Om
, p. 1781 - 1784 (2007/10/02)
Hypervalent iodine oxidation of various silyl enol ethers (aromatic, heteroaromatic, and aliphatic) using iodosobenzene-boron trifluoride diethyl ether-water provides a general and direct route for the α-hydroxylation of ketones.The structures of 2-hydroxy- (8) and 3-hydroxy-acetylpyridine (9) are discussed as well as the scope and mechanism of the reaction.
