Novel and efficient transformation of enamides into α-acyloxy ketones via an acyl intramolecular migration process
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
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.
Meissner, Anja,Boshoff, Helena I.,Vasan, Mahalakshmi,Duckworth, Benjamin P.,Barry III, Clifton E.,Aldrich, Courtney C.
p. 6385 - 6397
(2013/10/22)
REACTIONS OF 2-ACYLPYRIDINE 1-OXIDES WITH ACID ANHYDRIDES
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
Nagano, Hiroyuki,Hamana, Masatomo
p. 3249 - 3257
(2007/10/02)
Hypervalent Iodine Oxidation of Silyl Enol Ethers. A Direct Route to α-Hydroxy Ketones
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.
Moriarty, Robert M.,Duncan, Michael P.,Prakash, Om
p. 1781 - 1784
(2007/10/02)
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