- Synthesis of Aryl Methyl Ketones mediated by Cobalt Tetracarbonyl Anion
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The reaction of aryl halides with excess of methyl iodide in the presence of cobalt tetracarbonyl anion (generated under phase-transfer conditions), gave aryl ketones along with aromatic carboxylic acids.
- Miura, Masahiro,Akase, Fumiaki,Nomura, Masakatsu
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- Oxidation of secondary benzylic alcohols to ketones and benzylic oxygenation of alkylarenes with hydrogen peroxide in the presence of activated carbon
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A variety of benzylic alcohols were oxidized to the corresponding carbonyl compounds selectively with 30% hydrogen peroxide (H in the presence of activated carbon. Alkylarenes such as fluorenes, xanthenes, and anthrone were also effectively oxygenated to the corresponding carbonyl compounds with 30% Has oxidant in the presence of activated carbon. Georg Thieme Verlag Stuttgart · New York.
- Nishida, Shunsuke,Hayashi, Masahiko
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- Chiral ferrocenyl ligands with bidentate pyridine donors. Synthesis and application in Pd-catalyzed asymmetric allylic alkylation of 1,3-diphenylpropenyl-1-esters
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A synthetic procedure relying on the Friedlaender condensation of enantiopure α-amino ferrocenecarboxaldeyde has been devised for the regio-designed elaboration of a pyridine nucleus fused onto the ferrocene scaffold. Three novel bidentate ligands with different pyridine nitrogen donors featuring the [3,2-b]ferrocenopyridine fragment a as the sole chirogenic element have been prepared in enantiopure form through a multi step route involving the diastereoselective deprotonation of a chiral acetal of ferrocenecarboxaldehyde in the stereodetermining step. The ligands were assessed in the Pd-catalyzed allylic alkylation of 1,3-diphenyl-2-propenyl esters with good stereoselectivity.
- Mroczek, Agnieszka,Erre, Giulia,Taras, Rossana,Gladiali, Serafino
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- Chloroacetate-promoted selective oxidation of heterobenzylic methylenes under copper catalysis
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The efficient selective oxidation and functionalization of C-H bonds with molecular oxygen and a copper catalyst to prepare the corresponding ketones was achieved with ethyl chloroacetate as a promoter. In this transformation, various substituted N-heterocyclic compounds were well tolerated. Preliminary mechanistic investigations indicated that organic radical species were involved in the overall process. The N-heterocyclic compounds and ethyl chloroacetate work synergistically to activate C-H bonds in the methylene group, which results in the easy generation of free radical intermediates, thus leading to the corresponding ketones in good yields.
- Liu, Jianming,Zhang, Xin,Yi, Hong,Liu, Chao,Liu, Ren,Zhang, Heng,Zhuo, Kelei,Lei, Aiwen
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- 2-Quinolinecarboxaldehyde: an unusual partner in the Henry reaction and subsequent elimination
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2-Quinolinecarboxaldehyde participates in a standard Henry reaction when combined with a nitroalkane and catalytic amounts of base. However, water is not readily eliminated from the resulting β-nitro alcohol intermediate to form the expected nitroalkene. Instead, the elimination of nitrous acid is observed furnishing an unexpected ketone product.
- Nomland, Ashley,Hills, Ivory D.
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- Cu-catalyzed selective cascade sp3 C-H bond oxidative functionalization towards isoxazoline derivatives
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The first Cu-catalyzed cascade sp3 C-H bond oxidative functionalization of the 2-ethylazaarenes has been developed. The two different sp3 C-H bonds in 2-ethylazaarenes are selectively oxidized and four new types of bonds (CO, CN, C-C, C-O) are constructed in one operation. Starting from the simple substrates and cheap nitro source, this reaction provides an efficient approach to produce new kinds of isoxazolines.
- Wang, Gang-Wei,Cheng, Ming-Xing,Ma, Ran-Song,Yang, Shang-Dong
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- Simple and mild method for preparation of α-pyridinecarboxylates and α-pyridyl ketones via trimethylstannyl derivatives
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Alkoxycarbonylation and acylation at the α-position of pyridine, quinoline, and isoquinoline via the respective trimethylstannyl derivatives were satisfactorily performed by employing ethyl chloroglyoxylate and acylformyl chloride under mild conditions.
- Yamamoto,Ouchi,Tanaka
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Read Online
- Just Add the Gold: Aggregation-Induced-Emission Properties of Alkynylphosphinegold(I) Complexes Functionalized with Phenylene-Terpyridine Subunits
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A series of organometallic complexes containing an alkynylphosphinegold(I) fragment and a phenylene-terpyridine moiety connected together by flexible linker have been prepared using the specially designed terpyridine ligands. The compounds were studied cr
- Abramova, Evgenia O.,Paderina, Aleksandra V.,Slavova, Sofia O.,Kostenko, Ekaterina A.,Eliseenkov, Eugene V.,Petrovskii, Stanislav K.,Gitlina, Anastasia Yu.,Boyarskiy, Vadim P.,Grachova, Elena V.
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supporting information
p. 18715 - 18725
(2021/12/09)
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- Metal-, Photocatalyst-, and Light-Free Minisci C-H Acetylation of N-Heteroarenes with Vinyl Ethers
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Herein, we report a mild, operationally simple method for Minisci C-H acetylation of N-heteroarenes using vinyl ethers as robust, inexpensive acetyl sources. The reactions do not require a conventional photocatalysis, electrocatalysis, metal catalysis, light activation, or high temperature. This method is thus significantly more sustainable than previously reported methods in terms of cost, reagent toxicity, and waste generation. This protocol can be expected to obtain medically relevant molecules from abundant feedstock materials.
- Dong, Jianyang,Liu, Jianhua,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
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supporting information
p. 4374 - 4378
(2021/06/21)
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- Design, synthesis, and antibacterial evaluation of PFK-158 derivatives as potent agents against drug-resistant bacteria
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Infections caused by antibiotic resistant bacteria are a major health concern throughout the world. It is well known that PFK-158 can enhance the antibacterial effect of polymyxin, but its own anti-bactericidal effect is rarely discussed. In order to inve
- Wang, Wei,Zhang, You-Wen,Hu, Shang-Jiu,Niu, Wei-Ping,Zhang, Guo-Ning,Zhu, Mei,Wang, Ming-Hua,Zhang, Fan,Li, Xue-Mei,Wang, Ju-Xian
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supporting information
(2021/04/12)
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- Metal-free C-H methylation and acetylation of heteroarenes with PEG-400
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The generation of a methyl carbon source from renewable and cheap sources is challenging. Herein, we describe a novel and an efficient route for methylation and acetylation of aza-heteroarenes using PEG-400 under O2and TsOH·H2O for the first time by tuning the reaction conditions using a different set of starting materials. The key features of the current protocol are oxidative C-O and C-C bond scission under metal-free conditions with good functional group tolerance, and a broad substrate scope. The potential applicability of the designed methodology was demonstrated for the synthesis of central nervous system (CNS) depressant and anticonvulsant drug molecules by a one-pot strategy.
- Kudale, Vishal Suresh,Wang, Jeh-Jeng
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supporting information
p. 3506 - 3511
(2020/06/25)
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- Iron-Catalyzed Minisci Type Acetylation of N-Heteroarenes Mediated by CH(OEt)3/TBHP
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Iron-catalyzed acetylation of electron deficient N-heteroarenes has been reported using triethylorthoformate as robust and inexpensive acetyl source. This new method is successfully applied for the acetylation of quinolines, isoquinoline, quinoxalines, arylpyridines, bipyridines, and benzothiazole.
- Srinivasulu,Shantharjun,Vani,Ashalu, K. Chinna,Mohd,Wencel-Delord,Colobert,Reddy, K. Rajender
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supporting information
p. 1815 - 1819
(2019/02/20)
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- SUBSTITUTED DIHYDROPYRAZOLO PYRAZINE CARBOXAMIDE DERIVATIVES
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The invention relates to substituted dihydropyrazolo pyrazine carboxamide derivatives and to processes for their preparation, and also to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular cardiovascular disorders, preferably thrombotic or thromboembolic disorders, and diabetes, and also urogenital and ophthalmic disorders.
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- Metal-free C(sp3)–H oxidation of 2-methylquinolines with PIDA under microwave irradiation
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An efficient metal-free protocol has been developed for the sp3C–H bond oxidation of 2-methylquinolines in the presence of PIDA under microwave irradiation, providing 2-quinolinecarboxaldehydes with moderate to high yields and excellent selectivities. A wide range of 2-quinolinecarboxaldehydes with different functional groups have been synthesized. A tentative mechanism has been presented to explain this highly selective oxidation process.
- Jiang, Long,Huang, Yingyi,Yan, Yiyan,Xie, Yuanyuan
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supporting information
p. 4149 - 4151
(2016/08/24)
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- N ortho acyl substituted nitrogen-containing heterocyclic compound and process for preparing aminal iron (II) complexes thereof
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Provided are a process for preparing an N ortho acyl substituted nitrogen-containing heterocyclic compound and an aminal iron (II) complex thereof, and the use of the complexes obtained by the process in an olefin oligomerization catalyst. The N ortho acyl substituted nitrogen-containing heterocyclic compound in the present invention is for example 2-acyl-1,10-phenanthroline or 2,6-diacetyl pyridine as shown in formula b, and the N ortho acyl substituted nitrogen-containing heterocyclic compound in the present invention is produced by a reaction of a precursor thereof in a substituted or unsubstituted nitrobenzene. Preferably the precursor shown in formula I in the present invention is produced by 1,10-phenanthroline reacting with trialkyl aluminum, or a halogenoalkyl aluminum RnAIXm, or a substituted or unsubstituted benzyl lithium Ph′CH2Li, followed by hydrolysis. The preparation method provided in the present invention has a few synthetic steps, an easy process, a low toxic effect, and reduces the preparation costs of the catalyst, and has a promising outlook in the industrial application.
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Page/Page column 35
(2016/04/20)
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- Highly chemoselective and versatile method for direct conversion of carboxylic acids to ketones utilizing zinc Ate complexes
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Various carboxylic acids were directly transformed into the corresponding ketones by utilizing organozinc ate complexes, which provide high chemoselectivity without any overreaction to the undesired tertiary carbinol, owing to formation of a stable tetrahedral zincioketal intermediate. This method offers good overall atom/step/pot economy and operational simplicity. No need to overreact: Various carboxylic acids were directly transformed to the corresponding ketones by utilizing organozinc ate complexes, which provide high chemoselectivity without any overreaction to undesired tertiary carbinol, owing to formation of a stable tetrahedral zincioketal intermediate. This method offers good overall atom/step/pot economy and operational simplicity.
- Murata, Ryo,Hirano, Keiichi,Uchiyama, Masanobu
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supporting information
p. 1286 - 1290
(2015/06/08)
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- SUBSTITUTED AMINOTHIAZOLES AS INHIBITORS OF CANCERS, INCLUDING HEPATOCELLULAR CARCINOMA, AND AS INHIBITORS OF HEPATITIS VIRUS REPLICATION
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Pharmaceutical compositions of the invention are presented which comprise substiuted aminothiazoles derivatives. The substiuted aminothiazoles derivatives have a disease-modifying action in the treatment of diseases associated with unregulated cell growth. Such diseases include cancers such as hepatocellular carcinoma, and viral infections from a hepatitis virus.
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Paragraph 0140; 0141; 0146; 0147
(2013/04/24)
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- SUBSTITUTED 8 - AMINO - IMIDAZO [1, 2-A] PYRAZ1NES AS ANTIBACTERIAL AGENTS
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The present invention relates to substituted imidazo[1,2-a]pyrazines of Formula (I) and their use as antibacterial agents.
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(2013/02/27)
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- Tridentate N-donor palladium(II) complexes as efficient coordinating quadruplex DNA binders
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Fifteen complexes of palladium, platinum, and copper, featuring five different N-donor tridentate (terpyridine-like) ligands, were prepared with the aim of testing their G-quadruplex-DNA binding properties. The fluorescence resonance energy transfer melti
- Largy, Eric,Hamon, Florian,Rosu, Frederic,Gabelica, Valerie,De Pauw, Edwin,Guedin, Aurore,Mergny, Jean-Louis,Teulade-Fichou, Marie-Paule
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experimental part
p. 13274 - 13283
(2012/02/03)
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- Novel N,N-bidentate ligands for enantioselective copper(I)-catalyzed allylic oxidation of cyclic olefins
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New N,N-bidentate Schiff base ligands containing the 2-quinolyl moiety proved to be effective in conferring high reactivity and moderate to high enantioselectivity (up to 84% ee) to the copper(I)-catalyzed asymmetric allylic oxidation of various cylic ole
- Tan, Qitao,Hayashi, Masahiko
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supporting information; experimental part
p. 2639 - 2644
(2009/09/07)
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- New pyridine N-oxides as chiral organocatalysts in the asymmetric allylation of aromatic aldehydes
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Asymmetric allylation of aromatic aldehydes 1 with allyltrichlorosilane (2) can be catalyzed by new terpene-derived bipyridine N,N′-dioxides 12-15 and an axially chiral biisoquinoline dioxide 17b with good enantioselectivities. Dioxides have been found to be more reactive catalysts than their monooxide counterparts. Crown Copyright
- Malkov, Andrei V.,Westwater, Mary-Margaret,Gutnov, Andrey,Ramírez-López, Pedro,Friscourt, Frédéric,Kadl?íková, Aneta,Hoda?ová, Jana,Rankovic, Zoran,Kotora, Martin,Ko?ovsky, Pavel
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experimental part
p. 11335 - 11348
(2009/04/11)
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- Total synthesis of streptonigrone
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(Chemical Equation Presented) A total synthesis of streptonigrone, 1, is described, which incorporates a one-step synthesis of substituted pyridones devised in our laboratory. Other aspects of the synthesis that differentiate the present approach from previous ones are the use of a Conrad-Limpach reaction, rather than the customary Friedlaender methodology, to assemble the quinoline segment of 1, and the implementation of an anionic sequence for the functionalization of a key pyridone intermediate.
- Chan, Bryan K.,Ciufolini, Marco A.
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p. 8489 - 8495
(2008/02/13)
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- Oxidation of secondary benzylic alcohols to ketones by activated carbon-molecular oxygen system
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A variety of benzylic alcohols were oxidized to the corresponding carbonyl compounds selectively in the presence of activated carbon under molecular oxygen atmosphere. This process does not require any metal oxides, thus this is environmentally friendly and economical. Copyright
- Sano, Yuki,Tanaka, Takanori,Hayashi, Masahiko
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p. 1414 - 1415
(2008/03/14)
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- DIHYDROIMIDAZOTHIAZOLE DERIVATIVES
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Compounds of formula (I): or pharmaceutically acceptable salts thereof, exhibit 5-HT1A agonism in addition to noradrenaline reuptake inhibition and optionally also 5-HT reuptake inhibition are useful for the treatment of obesity.
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Page/Page column 20-21
(2008/06/13)
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- Syntheses of acetylquinolines and acetylisoquinolines via palladium-catalyzed coupling reactions
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Acetylquinolines and acetylisoquinolines were obtained from the corresponding chloro-, bromo- or trifluoromethylsulfonyloxy-heteroaromatics via four different palladium-catalyzed coupling reactions: (i) Stille coupling with tri(n-butyl)-1-ethoxyvinylstannane; (ii) Negishi coupling with 1-ethoxyvinylzinc chloride; (iii) cross-coupling with tri(1-ethoxyvinyl)indium; (iv) Heck arylation of n-butyl vinyl ether.
- Legros, Jean-Yves,Primault, Ga?lle,Fiaud, Jean-Claude
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p. 2507 - 2514
(2007/10/03)
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- Tricyclic quinoxalinediones
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Tricyclic quinoxalinediones of the formula: STR1 wherein X is alkyl, halogen, cyano, trifluoromethyl, nitro, hydroxy, amino, etc.; R 1 is H, etc.; R 2 is H, alkyl, cycloalkyl, alkenyl, alkynyl, cycloalkylalkyl, arylalkyl, substituted arylalkyl, aryl, or substituted aryl; W is H, CO 2 R 3, CO 2 Y, CONR 3 R 4, CONR 3 Y, CON(OR 3)R 4, COR 3, CN, tetrazolyl, or substituted alkyl; R 3 and R 4 independently are H, alkyl, cycloalkyl, alkenyl, alkynyl, etc.; Y is mono-substituted alkyl or di-substituted alkyl; and n is an integer 0 or 1, or a pharmaceutically acceptable salt thereof, which are useful as a selective antagonist of glutamate receptor for the treatment or prevention of various diseases in animals including human being, for example, minimizing damage of central nervous system induced by ischaemic or hypoxylic conditions, treatment and/or prevention of neurodegenerative disorders, and further analgesics, antidepressants, anxiolitics, and anti-schizophrenics.
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- polar effects in free-radical reactions. new homolytic substitutions of heteroaromatic bases and quinones by ethyl vinyl ether and hydroperoxides
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Trapping of l-butoxy radical by ethyl vinyl ether represents a strong evidence of the freeradical mechanism of the Gil reaction, in contrast with Barton's interpretation. The reaction has been developed from a synthetic point of view for new selective substitutions of heteroaromatic bases and quinones. The fundamental role of the polar effects in determining the selectivity is discussed.
- Minisci, Francesco,Fontana, Francesca,Bravo, Anna,Yan, Yong Ming
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- Homolytic Acylation of Protonated Pyridines and Pyrazines with α-Keto Acids: The Problem of Monoacylation
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The silver-catalyzed decarboxylation of α-keto acids by persulfate leads to acyl radicals, which can effect the selective homolytic acylation of pyridine and pyrazine derivatives.Compared with the previously developed source of acyl radicals by hydrogen abstraction from aldehydes, this procedure is more effective in monoacylation when multiple positions of high nucleophilic reactivity are available in the heterocyclic ring.Although the introduction of an acyl group strongly activates the heterocyclic ring toward further substitution, monoacylation can be achieved by taking advantage of the difference in basicity and lipophilicity between the starting base and the monoacylation products in a two-phase system.
- Fontana, Francesca,Minisci, Francesco,Barbosa, Maria Claudia Nogueira,Vismara, Elena
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p. 2866 - 2869
(2007/10/02)
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- Carbonylation of Aryl Halides and Vinyl Bromides Mediated by Tetracarbonylcobalt Anion
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The reaction of aryl halides (1a-g) with octacarbonyldicobalt in the presence of methyl iodide and sodium hydroxide under phase-transfer conditions was found to give a mixture of aryl methyl ketones (2a-g) and aromatic carboxylic acids (3a-h).From vinyl halides (9a-c), however, the corresponding carboxylic acids (10a-c) were obtained exclusively.
- Miura, Masahiro,Akase, Fumiaki,Shinohara, Masato,Nomura, Masakatsu
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p. 1021 - 1026
(2007/10/02)
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- Studies on Organometallic Compounds. III. Reaction of Trimethylstannylazines with Acyl Chlorides. A Novel C-C Bond Formation of Pyridine Nuclei
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Introduction of an acyl group at the α-, β-, and γ-positions of pyridine nuclei was accomplished. 2-Trimethylstannyl-pyridine and -quinoline and 1-trimethylstannylisoquinoline directly reacted with various acyl chlorides to give the corresponding 2-pyridyl, 2-quinolyl, and 1-isoquinolyl ketones, respectively.Reaction of 3-trimethylstannylpyridine, -quinoline, and -isoquinoline with acyl chlorides proceeded smoothly under catalysis by PdCl2 or PdCl2(PPh3)2 to afford the corresponding ketones in good yields.Similary, 4-pyridyl, -quinolyl, and -isoquinolyl ketones were prepared from corresponding 4-trimethylstannyl derivatives and acyl chlorides.Keywords--trimethylstannylazine; palladium-catalyzed reaction; acylation; palladium dichloride; dichlorobis(triphenylphosphine)palladium(II)
- Yamamoto, Yutaka,Yanagi, Akihiko
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p. 2003 - 2010
(2007/10/02)
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- A SIMPLE METHOD FOR INTRODUCTION OF ACYL GROUPS INTO PYRIDINE NUCLEI VIA TRIMETHYLSTANNYL-PYRIDINES AND QUINOLINES.
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The 2-trimethylstannyl (TMSn) derivatives of pyridine and quinoline were directly treated with acyl chlorides to afford the corresponding 2-acyl-pyridines and -quinolines in good yields.On the other hand, replacement of the 3- and 4-TMSn groups by acyl groups was satisfactorily achieved by catalysis of palladium compound such as PdCl2 or PdCl2(PPh3)2.
- Yamamoto, Yutaka,Yanagi, Akihiko
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- 2-Alkoxy(and 2-alkoxyalkyl)-2-heterocyclic-thioacetamides for inhibiting gastric acid secretion
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The compounds are 2-alkoxy(and 2-alkoxyalkyl)-2-heterocyclic-thioacetamides which are inhibitors of gastric acid secretion.
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