- Acid-catalyzed oxidation of furan derivatives by t-butyl hydroperoxide
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The unusual reactivity of t-butyl hydroperoxide under acid-catalysis allows the easy conversion of furan derivatives into 3(6H)-pyranones.
- Antonioletti, Roberto,Arista, Luca,Bonadies, Francesco,Locati, Ludovica,Scettri, Arrigo
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Read Online
- Rhodium-Catalyzed Remote Isomerization of Alkenyl Alcohols to Ketones
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We develop herein an efficient rhodium-catalyzed remote isomerization of aromatic and aliphatic alkenyl alcohols into ketones. This catalytic process, with a commercially available catalyst and ligand ([RhCl(cod)]2 and Xantphos), features high efficiency, low catalyst loading, good functional group tolerance, a broad substrate scope, and no (sub)stoichiometric additive. Preliminary mechanistic studies suggest that this transformation involves an iterative dissociative β-hydride elimination-migration insertion process.
- Dong, Wenke,Yang, Hongxuan,Yang, Wen,Zhao, Wanxiang
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supporting information
(2020/02/28)
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- A simple synthesis of ketone from carboxylic acid using tosyl chloride as an activator
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An effective process for the conversion of carboxylic acid to ketone has been discovered. In this process, carboxylic acid has been activated using p-toluene sulphonyl group. Under the optimized condition, aromatic, aliphatic heteroaromatic carboxylic acids have been proved to be good substrates for this methodology. The byproduct of this reaction can be removed very easily during work up process. Also, one equivalent of organometallic reagent is sufficient to complete this transformation.
- Jana, Samaresh,Sahoo, Debasis,Sarkar, Sohini
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supporting information
(2019/09/06)
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- Mild and direct conversion of esters to morpholine amides using diisobutyl(morpholino)aluminum: Application to efficient one-pot synthesis of ketones and aldehydes from esters
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Morpholine amide intermediates, which are easily prepared by aminolysis of various esters with diisobutyl(morpholino)aluminum, react with organolithium and reducing agents (DIBALH or LDBMA) without isolation of the aminolysis intermediates to give ketones in 83-95% yields and aldehydes quantitatively.
- Jeon, Ah Ram,Kim, Min Eai,Park, Jae Kyo,Shin, Won Kyu,An, Duk Keun
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p. 4420 - 4424
(2014/06/10)
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- An effective one-pot conversion of acid chlorides to aldehydes and ketones
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Aldehydes and ketones were synthesized from their respective acid chlorides via a one-pot protocol. Morpholine amide intermediates that were readily prepared by the aminolysis of various acid chlorides with diisobutyl(morpholino) aluminum smoothly reacted with the reducing agent LDBMA and the organolithium reagents under mild reaction conditions (0 C), giving almost excellent product yields of up to 95%.
- Park, Jae Kyo,Shin, Won Kyu,An, Duk Keun
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p. 3199 - 3203
(2013/06/27)
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- A Palladium Bipyridyl Complex Grafted onto Nanosized MCM-41 as a Heterogeneous Catalyst for Negishi Coupling
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The Negishi coupling of aryl bromides or acyl chlorides with organozinc chlorides catalyzed by a palladium bipyridyl complex anchored on nanosized mobile crystalline material 41 (MCM-41) were investigated. The reactions proceeded smoothly with a very low catalyst loading in THF at 70°C for electron-deficient aryl bromides, which gave good to high yields of the Negishi coupling products. However, reactions in toluene at 110°C were required if electron-rich aryl bromides were employed. For acyl chlorides, the reactions could be performed in THF at 50°C and the corresponding ketones and ynones were obtained in high yields. After centrifugation, it was possible to easily recover the supported catalyst from the reaction mixture, and this could be reused several times without any retreatment or regeneration with only a slight decrease in activity.
- Wu, Wei-Yi,Lin, Tze-Chiao,Takahashi, Tamotsu,Tsai, Fu-Yu,Mou, Chung-Yuan
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p. 1011 - 1019
(2013/05/09)
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- Discovery of a series of phosphonic acid-containing thiazoles and orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase
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Oral delivery of previously disclosed purine and benzimidazole fructose-1,6-bisphosphatase (FBPase) inhibitors via prodrugs failed, which was likely due to their high molecular weight (>600). Therefore, a smaller scaffold was desired, and a series of phosphonic acid-containing thiazoles, which exhibited high potency against human liver FBPase (IC50 of 10-30 nM) and high selectivity relative to other 5′-adenosinemonophosphate (AMP)-binding enzymes, were discovered using a structure-guided drug design approach. The initial lead compound (30j) produced profound glucose lowering in rodent models of type 2 diabetes mellitus (T2DM) after parenteral administration. Various phosphonate prodrugs were explored without success, until a novel phosphonic diamide prodrug approach was implemented, which delivered compound 30j with good oral bioavailability (OBAV) (22-47%). Extensive lead optimization of both the thiazole FBPase inhibitors and their prodrugs culminated in the discovery of compound 35n (MB06322) as the first oral FBPase inhibitor advancing to human clinical trials as a potential treatment for T2DM.
- Dang, Qun,Liu, Yan,Cashion, Daniel K.,Kasibhatla, Srinivas Rao,Jiang, Tao,Taplin, Frank,Jacintho, Jason D.,Li, Haiqing,Sun, Zhili,Fan, Yi,Dare, Jay,Tian, Feng,Li, Wenyu,Gibson, Tony,Lemus, Robert,Van Poelje, Paul D.,Potter, Scott C.,Erion, Mark D.
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scheme or table
p. 153 - 165
(2011/03/19)
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- Direct and efficient one-pot preparation of ketones from aldehydes using N-tert-butylphenylsulfinimidoyl chloride
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(Chemical Equation Presented) A general, one-pot process has been established to prepare ketones from aldehydes using N-tert- butylphenylsulfinimidoyl chloride. By employing the developed protocol, a range of unsymmetrical ketones has been prepared in good yields from aldehydes in one simple synthetic operation.
- Crawford, James J.,Henderson, Kenneth W.,Kerr, William J.
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p. 5073 - 5076
(2007/10/03)
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- Tetraorganogallate complexes in organic chemistry: A novel, efficient and versatile preparation of ketones from acyl chlorides
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Tetraorganogallium ate complexes, prepared in situ by addition of an organolithium reagent to a triorganogallium, reacted smoothly with acyl chlorides to yield ketones in high yields and mixed ate complexes display high chemoselectivity in the transfer of one of their ligands.
- Han, Ying,Fang, Lei,Tao, Wen-Tian,Huang, Yao-Zeng
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p. 1287 - 1290
(2007/10/02)
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- Benzotriazole-Mediated Conversions of Aromatic and Heteroaromatic Aldehydes to Functionalized Ketones
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Aromatic and heteroaromatic aldehydes reacted with benzotriazole and triethyl orthoformate in THF to give the corresponding α-(benzotriazol-1-yl)aryl ethyl ethers 7 in good yield.The novel acyl anion precursors 7 underwent smooth lithiation at the methine group followed by trapping with alkyl halides, aldehydes, ketones, and imines to yield the expected substituted intermediates of type 9, which were hydrolyzed under mild conditions without isolation.Benzaldehyde, methyl-, chloro-, and methoxy-substituted benzaldehydes, 1-naphthalenecarboxaldehyde, 2- and 3-furaldehydes, 2- and 3-thiophenecarboxaldehydes, and 2-pyridinecarboxaldehyde were all transformed in this manner into a variety of aryl and heteroaryl ketones with alkyl (10), α-hydroxyalkyl (12 and 13), α-aminoalkyl (14) and acyl (15) substituents.
- Katritzky, Alan R.,Lang, Hengyuan,Wang, Zuoquan,Zhang, Zhongxing,Song, Huimin
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p. 7619 - 7624
(2007/10/03)
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- Renin inhibitors
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A renin inhibiting compound of the formula: STR1 wherein X is O, NH or S and G is a mimic of the Leu-Val cleavage site of angiotensinogen; or a pharmaceutically acceptable salt, ester or prodrug thereof; with the proviso that the compound is not N-(3-(4-M
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- Synthesis of 3-Alkylcatechols via Intramolecular Cyclization
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The intramolecular cyclization of 2-alkanoyl-2,5-dimethoxytetrahydrofurans 4 with aqueous acid is described. 3-Alkylcatechols 7 were prepared in generally good yields by boiling the dioxane solution of compounds 4 in the presence of 1 M hydrochloric acid.In addition, 4,5-dioxoalkanals 6 were obtained in good to high yields when the dioxane solution of compounds 4 was treated with 0.1 M hydrochloric acid.
- Miyakoshi, Tetsuo,Togashi, Hiroyasu
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p. 407 - 410
(2007/10/02)
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- FUNCIONALIZED KETONES BY IRON MEDIETED REACTION OF GRIGNARD REAGENTS WITH ACYL CHLORIDES
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The iron(III)-catalyzed cross-coupling reaction between Grignard reagents and acyl chlorides was found to be widely applicable to the synthesis of various functionalized ketones in good yields under mild conditions; the series of examples includes the synthesis of chiral methyl ketones and symmetric diketones.
- Cardellicchio, C.,Fiandanese, V.,Marchese, G.,Ronzini, L.
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p. 2053 - 2056
(2007/10/02)
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- Reaction of Aldehyde O-Alkyl Oxime with Organometallic Compounds
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Aldehyde O-alkyl oximes were converted into ketones with high yields when they were treated with alkyllithium compounds or Grignard reagents followed by hydrolysis.Amines as reductive alkylation products of aldehyde O-alkyl oximes were also obtained by BH3 reduction before hydrolysis.
- Itsuno, Shinichi,Miyazaki, Koji,Ito, Koichi
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p. 3033 - 3036
(2007/10/02)
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