cas 701-49-5, 4-Fluoro-n-methylbenzamide | Articles data

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The Pd-catalyzed synthesis of difluoroethyl and difluorovinyl compounds with a chlorodifluoroethyl iodonium salt (CDFI)
Herein, we report a simple and efficient method for the direct installation of chlorodifluoroethyl group onto aromatic molecules of various aromatic amides with a new 2-chloro,2,2-difluoroethyl(mesityl)iodonium salt (CDFI). Moreover, the chlorodifluoroeth
Cao, Chengyao Kimmy,Chen, Chao,Ge, Chenxin,Niu, Yaru,Qu, Hongmei
supporting information

(2021/10/01)

Assemblies of 1,4-Bis(diarylamino)naphthalenes and Aromatic Amphiphiles: Highly Reducing Photoredox Catalysis in Water
Host-guest assemblies of a designed 1,4-bis(diarylamino)naphthalene and V-shaped aromatic amphiphiles consisting of two pentamethylbenzene moieties bridged by an m -phenylene unit bearing two hydrophilic side chains emerged as highly reducing photoredox catalysis systems in water. An efficient demethoxylative hydrogen transfer of Weinreb amides has been developed. The present supramolecular strategy permits facile tuning of visible-light photoredox catalysis in water.
Abe, Manabu,Akita, Munetaka,Chitose, Youhei,Hyodo, Yuki,Koike, Takashi,Takahashi, Keigo,Yoshizawa, Michito
(2021/10/21)

Rhodium-Catalyzed Electrooxidative C?H Olefination of Benzamides
Metal-catalyzed chelation-assisted C?H olefinations have emerged as powerful tools for the construction of functionalized alkenes. Herein, we describe the rhoda-electrocatalyzed C?H activation/alkenylation of arenes. The olefinations of challenging electron-poor benzamides were thus accomplished in a fully dehydrogenative fashion under electrochemical conditions, avoiding stoichiometric chemical oxidants, and with H2 as the only byproduct. This versatile alkenylation reaction also features broad substrate scope and used electricity as a green oxidant.
Ackermann, Lutz,Struwe, Julia,Zhang, Yan
p. 15076 - 15080
(2020/06/20)

Dealkoxylation ofN-alkoxyamides without an external reductant driven by Pd/Al cooperative catalysis
Lewis acid-assisted palladium-catalysed dealkoxylation ofN-alkoxyamides has been developed. This reaction proceeded smoothly with a range ofN-alkoxyamides in the absence of an external reductant, thereby establishing a convenient and reductant-free protocol. In addition, a gram-scale reaction could be achieved. Preliminary mechanistic investigations indicated that β-hydrogen elimination from a palladium alkoxide intermediate generated an intramolecular hydride source.
Suzuki, Hirotsugu,Shiomi, Takahiro,Yoneoka, Kenji,Matsuda, Takanori
supporting information
p. 7545 - 7548
(2020/10/15)

Rhenium-Catalyzed Phthalide Synthesis from Benzamides and Aldehydes via C-H Bond Activation
The [4 + 1] annulation of benzamides and aldehydes for phthalide synthesis was achieved via rhenium-catalyzed C-H activation, which demonstrates an unprecedented reaction pattern distinct from those of other transition-metal catalyses. The reaction also features readily available starting materials, a wide scope for both electro-rich and electro-deficient substrates, and the elimination of homoannulation byproducts.
Jia, Bing,Yang, Yunhui,Jin, Xiqing,Mao, Guoliang,Wang, Congyang
supporting information
p. 6259 - 6263
(2019/09/06)

Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)-N Bond Cleavage under Catalyst-Free Conditions
Conversion of a wide range of N-Boc amides to aryl ketones was achieved with Grignard reagents via chemoselective C(O)-N bond cleavage. The reactions proceeded under catalyst-free conditions with different aryl, alkyl, and alkynyl Grignard reagents. α-Ketoamide was successfully converted to aryl diketones, while α,β-unsaturated amide underwent 1,4-addition followed by C(O)-N bond cleavage to provide diaryl propiophenones. N-Boc amides displayed higher reactivity than Weinreb amides with Grignard reagents. A broad substrate scope, excellent yields, and quick conversion are important features of this methodology.
Sureshbabu, Popuri,Azeez, Sadaf,Muniyappan, Nalluchamy,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
p. 11823 - 11838
(2019/10/02)

Visible-Light-Driven Oxidation of N -Alkylamides to Imides Using Oxone/H 2 O and Catalytic KBr
Imides are prepared conveniently by visible-light-driven oxidations of various N -alkylamides under mild conditions. The majority of the reactions proceed efficiently by using Oxone as the oxidant in the presence of a catalytic amount of KBr in H 2 O/CH 2 Cl 2 under irradiation by an 8 W white LED at room temperature. Experimental studies suggest that an imine, obtained from the substrate amide via a radical process, is the key intermediate.
Mei, Chong,Hu, Yixin,Lu, Wenjun
supporting information
p. 2999 - 3005
(2018/05/25)

Palladium-Catalyzed Direct C-H Trifluoroethylation of Aromatic Amides
A simple and direct C-H trifluoroethylation of aromatic amides has been developed. The protocol is applicable to a variety of aromatic amides, including ones derived from amino acids. The developed method can be used for further modifications of peptides. Preliminary mechanistic studies have been done by isolating the reaction intermediate.
Maraswami, Manikantha,Pankajakshan, Sreekumar,Chen, Gang,Loh, Teck-Peng
supporting information
p. 4223 - 4226
(2017/08/23)

I2-Catalyzed Oxidative Amidation of Benzylamines and Benzyl Cyanides under Mild Conditions
We report a novel and efficient method for the oxidation of benzylic carbons (amines and cyanides) into corresponding benzamides using a catalytic amount of I2 and TBHP as the green oxidant via the C-H bond cleavage of the benzylic carbon under mild reaction conditions. According to the literature survey, this is the first report for the oxidative amidation of benzylamines and decyanation of benzyl cyanides in one pot under metal-free conditions.
Nageswara Rao, Sadu,Reddy, N. Naresh Kumar,Samanta, Supravat,Adimurthy, Subbarayappa
p. 13632 - 13642
(2017/12/26)

Aerobic thiyl radical addition/cyclization of N-methacryloyl benzamides for the synthesis of isoquinoline-1,3(2H,4H)-dione derivatives
A highly effective oxidative thiyl radical addition/cyclization of N-methacryloylbenzamides was explored using dioxygen as the sole terminal oxidant without the use of precious and/or toxic transition-metal catalysts. This method provides convenient access to a variety of useful sulfide-containing 4,4-disubstituted isoquinoline-1,3-diones by constructing C-S and C-C bonds in one step.
Yuan, Yan-Qin,Kumar, Pailla Santhosh,Zhang, Chun-Niu,Yang, Ming-Hua,Guo, Sheng-Rong
supporting information
p. 7330 - 7338
(2017/09/25)

Radical-mediated divergent cyclization of benzamides toward perfluorinated or cyanated isoquinolinediones
A simple and efficient copper-controlled divergent cyclization of benzamides, which leads to perfluorinated or cyanated isoquinolinediones, is developed. In the presence of AIBN, methacryloyl benzamides with perfluoroalkyl iodides undergo cascade radical addition/cyclization to afford perfluoroinated isoquinolinediones as the major product under metal-free conditions, whereas the use of CuI (10 mol%) is able to redirect the cyclization to yield isoquinolinediones bearing an α-cyano quaternary carbon center. The cyclization features controllable divergent synthesis and a broad substrate scope as well as highly practical reaction conditions, thereby making this strategy a highly attractive means to fluorinate or cyanate isoquinolinediones.
Deng, You-Lin,Tang, Shi,Ding, Guo-Liang,Wang, Ming-Wei,Li, Jie,Li, Zeng-Zeng,Yuan, Li,Sheng, Rui-Long
supporting information
p. 9348 - 9353
(2016/10/13)

One-Pot Direct Synthesis of Weinreb Amides from Aryl and Hetero Aryl Halides Using Co 2(CO) 8 as an Effective CO Source under Conventional Thermal Heating
A successful protocol for the synthesis of Weinreb amides directly from aryl halides via aminocarbonylation with N,O-dimethyl hydroxylamine using Co2(CO)8 as an in situ CO source has been demonstrated. The effects of various reaction parameters such as temperature, base, and CO source have also been investigated and optimized. GRAPHICAL ABSTRACT.
Baburajan, Poongavanam,Elango, Kuppanagounder P.
p. 541 - 548
(2015/10/29)

Re/Mg bimetallic tandem catalysis for [4+2] annulation of benzamides and alkynes via C-H/N-H functionalization
A rhenium-magnesium cocatalyzed [4+2] annulation of benzamides and alkynes via C-H/N-H functionalization is described. The reaction features a divergent and high level of diastereoselectivities, which are readily switchable by subtle tuning of reaction conditions. Thus, a wide range of both cis- and trans-3,4-dihydroisoquinolinones is expediently synthesized in a highly atom-economical manner. Moreover, mechanistic studies unraveled a tandem mode of action between rhenium and magnesium in the catalytic cycles.
Tang, Qiuzheng,Xia, Dexin,Jin, Xiqing,Zhang, Qing,Sun, Xiao-Qiang,Wang, Congyang
supporting information
p. 4628 - 4631
(2013/05/21)

Quantitative insights into energy contributions of intermolecular interactions in fluorine and trifluoromethyl substituted isomeric N-phenylacetamides and N-methylbenzamides
The presence of the C-F bond in organic molecules, particularly in the context of generating different intermolecular interactions of the type C-F...F-C, C-H...F and C-F...π is of extreme significance in the realm of structural chemistry. These interactions generate different packing motifs in the formation of the crystal. It is of interest to evaluate the energetic contributions of such weak interactions to evaluate their important role in crystal packing. In this respect, a library of twelve compounds containing a strong donor and acceptor, along with the presence of a C-F bond in different electronic environments (fluorine atom connected to C(sp2) and C(sp3) carbon atom) have been synthesized and characterized using single crystal X-ray diffraction studies at low temperature. In addition, the non-fluorinated counterpart has also been synthesized. These crystal structures have been analyzed to understand the contribution of weak interactions involving organic fluorine in the crystal packing. Furthermore, the stabilizing-destabilizing roles of such interactions in terms of favourable energetics have been quantified with inputs from calculations performed using PIXEL. It is observed that most of the interactions involving fluorine are of a dispersive character, and in some cases the interaction is also coulombic in origin. These results have been compared with ab initio quantum-chemical calculations (DFT-D3/B-97D level) performed using TURBOMOLE. In addition, the lattice energies of all the compounds have been evaluated, and the total contribution partitioned into the corresponding coulombic, polarization, dispersion and exchange contributions using the CLP module. The results correlate well with thermochemical data experimentally determined for these compounds.
Panini, Piyush,Chopra, Deepak
p. 3711 - 3733
(2013/07/26)

Discovery of novel benzo[b][1,4]oxazin-3(4H)-ones as poly(ADP-ribose) polymerase inhibitors
Structure based drug design of a series of novel 1,4-benzoxazin-3-one derived PARP-1 inhibitors are described. The synthesis, enzymatic & cellular activities and pharmacodynamic effects are described. Optimized analogs demonstrated inhibition of poly-ADP-ribosylation in SW620 tumor bearing nude mice through 24 h following a single dose.
Gangloff, Anthony R.,Brown, Jason,De Jong, Ron,Dougan, Douglas R.,Grimshaw, Charles E.,Hixon, Mark,Jennings, Andy,Kamran, Ruhi,Kiryanov, Andre,O'Connell, Shawn,Taylor, Ewan,Vu, Phong
supporting information
p. 4501 - 4505
(2013/08/15)

Copper-catalyzed N-methylation of amides and O-methylation of carboxylic acids by using peroxides as the methylating reagents
The copper-catalyzed N-methylation of amides and O-methylation of carboxylic acids by using peroxides as the methylating reagent are described. Various amides and carboxylic acids were methylated affording N-substituted amides and esters. Tentative mechanistic studies suggest that this reaction is likely to involve a radical process.
Xia, Qinqin,Liu, Xiaolong,Zhang, Yuejiao,Chen, Chao,Chen, Wanzhi
supporting information
p. 3326 - 3329
(2013/07/26)

Peptide fragment coupling using a continuous-flow photochemical rearrangement of nitrones
Go with the flow: A general approach for amide bond formation by way of a continuous-flow photochemical rearrangement of nitrones was described (see scheme). Simple aryl-alkyl amide bonds as well as complex peptide bonds were constructed efficiently with a residence time less than 20minutes. A tetrapeptide was synthesized in this way and the method could be applied to peptide fragment coupling. Copyright
Zhang, Yuan,Blackman, Melissa L.,Leduc, Andrew B.,Jamison, Timothy F.
supporting information
p. 4251 - 4255
(2013/05/08)

Transition metal-free one-pot synthesis of 2-substituted 3-carboxy-4-quinolone and chromone derivatives
A novel one-pot synthesis of the 2-substituted 3-carboxy-4-quinolone/ chromone derivatives from readily available 3-oxo-3-arylpropanoates and amides/acyl chlorides is reported, without any transition metal aid. The Royal Society of Chemistry 2013.
Lin, Jian-Ping,Long, Ya-Qiu
supporting information
p. 5313 - 5315
(2013/06/27)

Ruthenium-catalyzed oxidative annulation by cleavage of C-H/N-H bonds
Bond activation in action: Unprecedented ruthenium-catalyzed oxidative annulations of alkynes through cleavage of C-H bonds set the stage for an efficient 1(2H)-isoquinolone synthesis with ample scope (see scheme; tAm=tert-amyl). Mechanistic studies provided strong evidence for a rate-limiting C-H bond metalation through carboxylate assistance. Copyright
Ackermann, Lutz,Lygin, Alexander V.,Hofmann, Nora
supporting information; experimental part
p. 6379 - 6382
(2011/09/12)

AZETIDINES AND CYCLOBUTANES AS HISTAMINE H3 RECEPTOR ANTAGONISTS
The invention relates to compounds of formula (I) wherein R, R0, R1, m, n and X1 to X4 have the meaning as cited in the description and the claims. Said compounds are useful as Histamine H3 receptor antagonists. The invention also relates to pharmaceutical compositions, the preparation of such compounds as well as the production and use as medicament.
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Page/Page column 67-68

(2010/01/29)

Metal-free reductive cleavage of N-O bonds in weinreb amides by an organic neutral super-electron donor
The scope of neutral organic super-electron donors as reducing agents has been extended to include the reductive cleavage of N-O bonds in Weinreb amides. This methodology proved to be applicable to a large array of substrates to afford their reduced counterparts in good to excellent yields. The variation in reactivity within the set of tested amides is rationalised. Georg Thieme Verlag Stuttgart.
Cutulic, Sylvain P. Y.,Murphy, John A.,Farwaha, Hardeep,Zhou, Sheng-Ze,Chrystal, Ewan
experimental part
p. 2132 - 2136
(2009/04/08)

Room-temperature debenzylation of N-benzylcarboxamides by N-bromosuccinimide
A simple and highly efficient method has been developed with which to cleave the N-benzyl group on N-mono- or disubstituted carboxamides using N-bromosuccinimide (NBS) at room temperature. All the 31 substrates examined showed moderate to excellent deprotection yields. Our study also indicated that the debenzylation may involve an oxygen/light initiated free radical mechanism. Georg Thieme Verlag Stuttgart.
Kuang, Liping,Zhou, Jing,Chen, Sheng,Ding, Ke
p. 3129 - 3134
(2008/03/28)

Efficient tandem process for the catalytic deprotection of N-allyl amides and lactams in aqueous media: A novel application of the bis(allyl)- ruthenium(IV) catalysts [Ru(η3:η2: η3-C12H18)Cl2] and [Ru(η3:η3-C10H16)-(μ-Cl) Cl}2]
An operationally simple and highly efficient methodology for the removal of the allyl protecting group in amides and lactams has been developed by using the commercially available bis(allyl)-ruthenium(IV) catalysts [Ru(η3:η2:η3-C12H 18)Cl2] (C12H18 = dodeca-2,6,10-triene-1,12-diyl) and [(Ru(η3:η3- C10H16)(μ-Cl)Cl}2] (C10H 16 = 2,7-dimethylocta-2,6-diene-1,8-diyl). The tandem process, which takes place in aqueous media and proceeds in a one-pot manner, involves the initial isomerization of the C=C bond of the allyl unit and subsequent oxidative cleavage of the resulting enamide.
Cadierno, Victorio,Gimeno, Jose,Nebra, Noel
p. 6590 - 6594
(2008/03/13)

SUBSTITUTED PIPERIDINES AS HISTAMINE H3 RECEPTOR LIGANDS
The present invention relates to novel piperidine ether derivatives having affinity for the histamine H3 receptor, processes for their preparation, to compositions containing them and to their use in the treatment of neurological and psychiatric disorders.
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Page/Page column 20-21

(2010/02/10)

N-methylation of substituted benzonitriles with methyl fluorosulfonate
Substituted benzonitriles ArCN treated at 20-70°C with methyl fluorosulfonate yield the corresponding N-methylbenzamides ArCONHMe. Compounds with two cyano groups afford N,N′-methylated diamides.
Salfetnikova,Vasil'ev,Rudenko
p. 838 - 844
(2007/10/03)

Cyclic amide derivatives for treating asthma
Compounds of formula I STR1 wherein Q1, Q2, Q3, and Q4 have any of the meanings given in the specification, their N-oxides, and their pharmaceutically acceptable salts are nonpeptide antagonists of neurokinin A and useful for the treatment of asthma, etc. Also disclosed are pharmaceutical compositions, processes for preparing the compounds of formula I and intermediates.
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(2008/06/13)

Cationic Carbon to Nitrogen Rearrangements in the Reactions of N-(Sulfonyloxy)amines with Aldehydes
A series of aromatic and aliphatic aldehydes was reacted with N-((p-nitrobenzenesulfonyl)oxy)methylamine in chloroform.Products resulting from both carbon migration and hydride migration to nitrogen were isolated.The ratios of carbon to hydride migration products were used to clarify the reaction mechanism.The results support a two-step process in which cationic carbon to nitrogen rearrangements is rate determining.
Hoffman, Robert V.,Salvador, James M.
p. 4487 - 4490
(2007/10/02)

p-Fluorobenzoyl Chloride for Characterization of Active Hydrogen Functional Groups by Fluorine-19 Nuclear Magnetic Resonance Spectrometry
The base-catalyzed reactions of p-fluorobenzoyl chloride provide a convenient method for (19)F NMR analysis of alcohols, phenols, carboxylic acids, amines, and thiols.The (19)F chemical shift and yield data for p-fluorobenzoyl derivatives for nearly 100 compounds are presented.The yield data for these p-fluorobenzoyl derivatives suggest a simple, and in many cases, quantitative method for introducing a fluorine tagging group.The (19)F chemical shifts indicate a wide chemical shift range (ca. 10 ppm) for a large number of compounds.Furthermore, most chemical classes (e.g., phenols, alcohols, etc.) have fairly well resolved chemical shift regions.
Spratt, M. P.,Dorn, H. C.
p. 2038 - 2043
(2007/10/02)