cas 122334-36-5, 4,N-DIMETHYL-N-METHOXYBENZAMIDE

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Efficient palladium-catalyzed aminocarbonylation of aryl iodides using palladium nanoparticles dispersed on siliceous mesocellular foam
A highly dispersed nanopalladium catalyst supported on mesocellular foam (MCF), was successfully used in the heterogeneous catalysis of aminocarbonylation reactions. During the preliminary evaluation of this catalyst it was discovered that the supported palladium nanoparticles exhibited a "release and catch" effect, meaning that a minor amount of the heterogeneous palladium became soluble and catalyzed the reaction, after which it re-deposited onto the support. It's catchy! An efficient palladium-catalyzed protocol for the aminocarbonylation of aryl iodides is reported in which the palladium immobilized on the amino-functionalized mesocellular foam (MCF) was found to operate through a "release and catch" mechanism (see scheme). A very low content of palladium was found in solution upon completion of the reaction and a variety of different aryl iodides were converted to the corresponding amides under mild conditions.
Tinnis, Fredrik,Verho, Oscar,Gustafson, Karl P. J.,Tai, Cheuk-Wai,Baeckvall, Jan-E.,Adolfsson, Hans
p. 5885 - 5889
(2014)
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Amide Bond Formation via the Rearrangement of Nitrile Imines Derived from N-2-Nitrophenyl Hydrazonyl Bromides
We report how the rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance of this approach was exemplified by the N-acylation of unprotected amino acids.
Boyle, Mhairi,Livingstone, Keith,Henry, Martyn C.,Elwood, Jessica M. L.,Lopez-Fernandez, J. Daniel,Jamieson, Craig
supporting information
p. 334 - 338
(2022/01/20)

Deoxygenative hydroboration of primary, secondary, and tertiary amides: Catalyst-free synthesis of various substituted amines
Transformation of relatively less reactive functional groups under catalyst-free conditions is an interesting aspect and requires a typical protocol. Herein, we report the synthesis of various primary, secondary, and tertiary amines through hydroboration of amides using pinacolborane under catalyst-free and solvent-free conditions. The deoxygenative hydroboration of primary and secondary amides proceeded with excellent conversions. The comparatively less reactive tertiary amides were also converted to the corresponding N,N-diamines in moderate yields under catalyst-free conditions, although alcohols were obtained as a minor product.
Yi, Jaeeun,Kim, Hyun Tae,Jaladi, Ashok Kumar,An, Duk Keun
supporting information
p. 129 - 132
(2021/11/17)

Phase-Transfer Catalyzed Asymmetric [4 + 1] Annulations for the Synthesis of Chiral 2,2-Disubstituted Tetrahydrothiophenes
An efficient catalytic asymmetric [4 + 1] reaction, which features the use of simple β-keto esters as one-carbon nucleophiles and 5-succinimidothio-pent-2-enoates as four-atom bielectrophiles, has been developed in the presence of a bifunctional chiral ph
Yin, Qi,Wen, Xiaolu,Chen, Yiwei,Gong, Xiangnan,Hu, Lin
supporting information
p. 7529 - 7534
(2021/10/02)

A CO2-Catalyzed Transamidation Reaction
Transamidation reactions are often mediated by reactive substrates in the presence of overstoichiometric activating reagents and/or transition metal catalysts. Here we report the use of CO2as a traceless catalyst: in the presence of catalytic amounts of CO2, transamidation reactions were accelerated with primary, secondary, and tertiary amide donors. Various amine nucleophiles including amino acid derivatives were tolerated, showcasing the utility of transamidation in peptide modification and polymer degradation (e.g., Nylon-6,6). In particular,N,O-dimethylhydroxyl amides (Weinreb amides) displayed a distinct reactivity in the CO2-catalyzed transamidation versus a N2atmosphere. Comparative Hammett studies and kinetic analysis were conducted to elucidate the catalytic activation mechanism of molecular CO2, which was supported by DFT calculations. We attributed the positive effect of CO2in the transamidation reaction to the stabilization of tetrahedral intermediates by covalent binding to the electrophilic CO2
Yang, Yang,Liu, Jian,Kamounah, Fadhil S.,Ciancaleoni, Gianluca,Lee, Ji-Woong
p. 16867 - 16881
(2021/11/18)

Rhoda-Electrocatalyzed Bimetallic C?H Oxygenation by Weak O-Coordination
Rhodium-electrocatalyzed arene C?H oxygenation by weakly O-coordinating amides and ketones have been established by bimetallic electrocatalysis. Likewise, diverse dihydrooxazinones were selectively accessed by the judicious choice of current, enabling twofold C?H functionalization. Detailed mechanistic studies by experiment, mass spectroscopy and cyclovoltammetric analysis provided support for an unprecedented electrooxidation-induced C?H activation by a bimetallic rhodium catalysis manifold.
Tan, Xuefeng,Massignan, Leonardo,Hou, Xiaoyan,Frey, Johanna,Oliveira, Jo?o C. A.,Hussain, Masoom Nasiha,Ackermann, Lutz
supporting information
p. 13264 - 13270
(2021/05/06)

Synthesis of various acylating agents directly from carboxylic acids
A straightforward synthesis of acylating reagents such as Weinreb and MAP amides from aromatic, aliphatic carboxylic acids, and amino acids using PPh3/NBS combination is described. A chemo-selective modification of the carboxylic acid group into Weinreb amide in the presence of more reactive aldehydes and ketones is presented. All reactions were performed at ambient temperature under air using undried commercial grade solvent. Furthermore, the present methodology could be performed at a gram scale under inert-free reaction conditions. In addition, 7-azaindoline amide auxiliary (used for catalytic asymmetric aldol- and Mannich-type reactions), which behaves like Weinreb amide is also synthesized under similar reaction conditions.
Pilathottathil, Fathima,Vineet Kumar, Doppalapudi,Kaliyamoorthy, Alagiri
supporting information
p. 1622 - 1632
(2020/04/27)

Potent Analogues of Abscisic Acid – Identifying Cyano-Cyclopropyl Moieties as Promising Replacements for the Cyclohexenone Headgroup
Synthetic analogues of plant hormone abscisic acid (ABA) bearing a yet unexplored head group motif were prepared based on a combination of agrochemical experience, in vivo hits and structure-based design. It could thus be explored how modifying key parts of ABA's cyclohexenone unit influenced receptor affinity and in vivo efficacy against drought stress in selected crops. Cyano-cyclopropyl groups proved to be suitable replacements of the cyclohexanone moiety leading to ABA analogues with strong activity in vitro and in vivo. Their efficient and versatile synthesis proceeded via Stille or Sonogashira couplings as the key steps. Combining novel cyano-cyclopropyl headgroups with previously identified substituents in the terpenoid side chain afforded the most promising effects against drought stress in crops, particularly canola and wheat.
Frackenpohl, Jens,Bojack, Guido,Baltz, Rachel,Bickers, Udo,Busch, Marco,Dittgen, Jan,Franke, Jana,Freigang, J?rg,Grill, Erwin,Gonzalez, Susana,Helmke, Hendrik,Hills, Martin J.,Hohmann, Sabine,von Koskull-D?ring, Pascal,Kleemann, Jochen,Lange, Gudrun,Lehr, Stefan,Schmutzler, Dirk,Schulz, Arno,Walther, Kerstin,Willms, Lothar,Wunschel, Christian
p. 1416 - 1425
(2018/04/06)

Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides
A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.
Das, Riki,Kapur, Manmohan
p. 1114 - 1126
(2018/06/18)

Mo(CO)6 as a Solid CO Source in the Synthesis of Aryl/Heteroaryl Weinreb Amides under Microwave-Enhanced Condition
The facile transformation of aryl/heteroaryl nonaflates into corresponding amides via Pd-catalyzed aminocarbonylation using Mo(CO)6 as a solid CO source under microwave-enhanced condition is reported. The method was found to be tolerant with respect to a
Ningegowda, Raghu,Bhaskaran, Savitha,Sajith, Ayyiliath M.,Aswathanarayanappa, Chandrashekar,Padusha, M. Syed Ali,Priya, Babu Shubha
p. 44 - 51
(2017/01/21)

DIHYDROPYRAZOLOPYRIMIDINONE COMPOUNDS AS PDE2 INHIBITORS
The present invention is directed to dihydropyrazolopyrimidinonecompounds of formula (I) which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 2 (PDE2). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis, Parkinson's disease, Parkinson's disease dementia (PDD), or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.
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(2016/12/22)

Copper-catalyzed synthesis of weinreb amides by oxidative amidation of alcohols
A simple and efficient protocol has been developed for the oxidative amidation of alcohols to Weinreb amides using tert-butyl hydroperoxide as an oxidant and an inexpensive and air stable copper catalyst. The present protocol is advantageous as it uses commercially affordable alcohols as starting materials. The developed protocol also tolerates various substituted alcohols as starting materials to provide good to excellent yields of the desired products.
Yedage, Subhash L.,Bhanage, Bhalchandra M.
p. 526 - 532
(2015/02/19)

An Efficient synthesis of Weinreb amides and ketones via palladium nanoparticles on ZIF-8 catalysed carbonylative coupling
Heterogeneously catalysed carbonylative coupling reactions such as aminocarbonylation and Suzuki-carbonylation are reported using Pd nanoparticles supported on ZIF-8 for efficient and environmentally attractive synthesis of Weinreb amides and ketones from aryl bromides or iodides. The catalyst is air stable, offers high activity with very low palladium leaching and is recyclable. The presence of a phosphine ligand was required when aryl bromides were used as substrates, while no ligand was necessary when aryl iodides were used. the Partner Organisations 2014.
Thanh Dang, Tuan,Chen, Anqi,Majeed Seayad, Abdul
p. 30019 - 30027
(2014/08/05)

One-pot transition-metal-free synthesis of weinreb amides directly from carboxylic acids
Weinreb amides were prepared directly from carboxylic acids, N,O-dimethylhydroxylamine, and phosphorus trichloride in one pot at 60 °C in toluene in high yields, thus avoiding the separation of the moisture and air sensitive intermediate P[NMe(OMe)]3 in advance. Sterically hindered carboxylic acids also give the corresponding Weinreb amides in excellent yields. Various functional groups are tolerated on the carboxylic acid. The method, which is a simple process and gives high yields, is suitable for large-scale production. Georg Thieme Verlag KG Stuttgart · New York.
Niu, Teng,Wang, Ke-Hu,Huang, Danfeng,Xu, Changming,Su, Yingpeng,Hu, Yulai,Fu, Ying
p. 320 - 330
(2014/02/14)

Design, synthesis, and biological evaluation of potent thiosemicarbazone based cathepsin L inhibitors
A small library of 36 functionalized benzophenone thiosemicarbazone analogs has been prepared by chemical synthesis and evaluated for their ability to inhibit the cysteine proteases cathepsin L and cathepsin B. Inhibitors of cathepsins L and B have the potential to limit or arrest cancer metastasis. The six most active inhibitors of cathepsin L (IC50 50 > 10,000 nM). The most active analog in the series, 3-bromophenyl-2′-fluorophenyl thiosemicarbazone 1, also efficiently inhibits cell invasion of the DU-145 human prostate cancer cell line.
Kishore Kumar,Chavarria, Gustavo E.,Charlton-Sevcik, Amanda K.,Arispe, Wara M.,MacDonough, Matthew T.,Strecker, Tracy E.,Chen, Shen-En,Siim, Bronwyn G.,Chaplin, David J.,Trawick, Mary Lynn,Pinney, Kevin G.
supporting information; experimental part
p. 1415 - 1419
(2010/07/06)

Phthalides by rhodium-catalyzed ketone hydroacylation
(Chemical Equation Presented) Phthalides are biologically relevant five-membered lactones found in herbs, fruits, and vegetables. Herein we communicate the first atom-economical approach to phthalides by using enantioselective ketone hydroacylation. In the presence of Rh[(Duanphos)]X (X = NO3, OTf, OMs), various 2-ketobenzaldehydes undergo intramolecular hydroacylation to produce phthalide products in good yields and 92-98% ee's. Our study highlights the key role counterions play in controlling both reactivity and enantioselectivity. A concise asymmetric total synthesis of the celery extract (S)-(-)-3-n-butylphthalide is also presented.
Phan, Diem H. T.,Kim, Byoungmoo,Dong, Vy M.
supporting information; experimental part
p. 15608 - 15609
(2010/01/30)

A powerful reagent for synthesis of weinreb amides directly from carboxylic acids
A powerful reagent, P[NCH3(OCH3)]3 (3), for conversion of carboxylic acids directly to Weinreb amides was developed. In most cases the yields of the corresponding Weinreb amides were above 90% when P[NCH3(OCHsu
Niu, Teng,Zhang, Weiming,Huang, Danfeng,Xu, Changming,Wang, Haifeng,Hu, Yulai
scheme or table
p. 4474 - 4477
(2009/12/24)

Weinreb amide based new synthetic equivalents for convenient access to immunosuppressive agent FTY720 and analogues
Three new synthetic equivalents containing Weinreb amide functionality for the central core of FTY720, an immunosuppressive agent, have been developed. These synthetic equivalents enabled incorporation of the polar head group of FTY720, through Julia, Wit
Balasubramaniam, Sivaraman,Annamalai, Senthilmurugan,Aidhen, Indrapal Singh
p. 2841 - 2846
(2008/02/13)

HETEROCYCLIC COMPOUND DERIVATIVES AND MEDICINES
The present invention provides a compound which is useful as a PGI2 receptor agonist, and a pharmaceutical composition. The present invention is directed to a pharmaceutical composition comprising a compound represented by the following formula [1]: (R1 and R2 are the same or different and each represents optionally substituted aryl, Y represents N or CH, Z represents N or CH, A represents NH, NR5, O, S, or ethylene, R5 represents alkyl, D represents alkylene or alkenylene, E represents phenylene or single bond, G represents O, S, or CH2, R3 and R4 are the same or different and each represents hydrogen or alkyl, Q represents carboxy, alkoxycarbonyl, tetrazolyl, carbamoyl, or N-(alkylsulfonyl)carbamoyl), or a pharmaceutically acceptable salt thereof as an active ingredient.
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Page 29

(2010/02/05)

The α-effect in methyl transfers from S-methyldibenzothiophenium fluoroborate to substituted N-methylbenzohydroxamates
Studies of the α-effect show increased reactivity of nucleophiles having lone pairs of electrons on atoms neighboring the lone pair involved in reactivity when compared to the basicity of the nucleophiles. Hammett-type plots and Broensted-type plots of substituted methylphenyl sulfates vs hydrogen peroxide anions and substituted N-methylbenzohydroxanates (NMBH) with substituted methylarenesulfonates or substituted arenedimethylsulfonium ions have large ρ or βnuc values, indicating a putative tightening of the usual SN2 transition states (anti-Hammond effect). Electrochemical studies of SN2-SET or reactivity indicate that SET character occurs in looser transition states, whereas SN2 transition states are associated with greater tightness. The α-effects for the series of sulfonium salts in completion reactions for 3-ClNMBH anions and 3-nitrophenolate anions are (log kα/knormal) 1.124 for dimethylphenyl sulfonium, 1.512 for dimethyl-1-naphthyl sulfonium, 1.835 for dimethyl-9-anthracenyl sulfonium, and 1.137 for S-methyldibenzylthiophenium. Correlations of the sizes of α-effects with typical SET (or ET) experimental parameters and the inverse dependence of the size of the α-effect on electron demand indicate inclusion of SET character in these SN2 transition states, vs no (or at least diminished) SET character in normal transition states. This dichotomy of tighter SN2 transition states, but looser SET transition states indicated in the α-effect, is examined in the present work.
Fountain,Felkerson, Cassie J.,Driskell, Jeremy D.,Lamp, Brian D.
p. 1810 - 1814
(2007/10/03)

An Efficient One-Pot Synthesis of N-Methoxy-N-methylamides from Carboxylic Acids
Several N-methoxy-N-methylamides were prepared by the reaction of the corresponding carboxylic acids with N,O-dimethylhydroxylamine hydrochloride at room temperature using trichloromethyl chloroformate in the presence of triethylamine in excellent yields.
Kim, Misoo,Lee, Hagyoung,Han, Ki-Jong,Kay, Kwang-Yol
p. 4013 - 4018
(2007/10/03)

A one-flask synthesis of weinreb amides from chiral and achiral carboxylic acids using the deoxo-fluor fluorinating reagent
(Matrix presented) The reagent [bis(2-methoxyethyl)amino]sulfur trifluoride (Deoxo-Fluor reagent) converts carboxylic acids to the corresponding acid fluorides, which then react with N,N-dimethylhydroxylamine to give the corresponding Weinreb amides in high yields. The reaction proceeds without racemization when optically active acids are used as the starting material. This method is operationally simple and provides the products in high purity.
Tunoori, Ashok Rao,White, Jonathan M.,Georg, Gunda I.
p. 4091 - 4093
(2007/10/03)

One-pot synthesis of ketones using N-methoxy-N-methyl-2-pyridyl urethane
The one-pot reaction of N-methoxy-N-methyl-2-pyridyl urethane with Grignard and organolithium reagents provided an efficient method for the preparation of unsymmetrical ketones.
Lee, Na Ra,Lee, Jae In
p. 1249 - 1255
(2007/10/03)

The sydnone ring as an ortho-director of lithiation. 2. Dilithiation of 3-phenylsydnone and regiospecific @?o-aryl acylation using N-methoxy-N-methylamides
Readily available 3-phenylsydnone (1) reacts with n-butyllithium/TMEDA to form the dilithio species 2 which can be regiospecifically acylated at the ortho-aryl position using N-methoxy-N-methylamides (Weinreb's amides).
Turnbull, Kenneth,Sun, Congcong,Krein, Douglas M.
p. 1509 - 1512
(2007/10/03)

Palladium-catalyzed coupling reactions of N-methoxy-N-methylcarbamoyl chloride for the synthesis of N-methoxy-N-methylamides
A new synthetic method of N-methoxy-N-methylamides is developed. The palladium-catalyzed coupling reaction of N-methoxy-N-methylcarbamoyl chloride furnished N-methoxy-N-methylamide in moderate to good yield, wherein a carbonyl equivalent was appended to s
Murakami, Masahiro,Hoshino, Yujiro,Ito, Hajime,Ito, Yoshihiko
p. 163 - 164
(2007/10/03)

Design and Synthesis of Novel and Potent Monoamine Oxidase Inhibitors
Reversible and selective monoamine oxidase-A inhibitors (RIMA's) like moclobemide (Aurorix) have rehabilitated the use of MAO inhibitors as drugs of choice in depression.Starting from the structure of moclobemide, we tried to identify novel
Branca, Quirico,Jakob-Roetne, Roland,Kettler, Rolf,Roever, Stephan,Scalone, Michelangelo
p. 381 - 385
(2007/10/03)

Reactivity patterns of N-methylbenzhydroxamates. I. Studies of methyl transfer between N-methylbenzhydroxamates and arenesulfonates
The rates of methyl transfer between benzohydroxamates and sulfonates show large βnuc values (ca. 0.8) indicating much charge transfer to the C atom, similar to the results of N,N-dialkylaminofluorene anions.A small α effect shows that even in
Fountain, Kenneth R.,Fountain, Daniel P.,Michaels, Bernice,Myers, D. Brenton,Salmon, Jon K.,et al.
p. 798 - 810
(2007/10/02)