- Anodic oxidation of bisamides from diaminoalkanes by constant current electrolysis
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In general, bisamides derived from diamines and involving 3 and 4 methylene groups as spacers between the two amide functionalities behave similar to monoamides upon anodic oxidation in methanol/LiClO4 because both types undergo majorly mono- and dimethoxylations at the α-position to the N atom. However, in cases where the spacer contains two methylene groups only the anodic process leads mostly to CH2-CH2 bond cleavage to afford products of type RCONHCH2OCH3. Moreover, upon replacing LiClO4 with Et4NBF4 an additional fragmentation type of product was generated from the latter amides, namely RCONHCHO. Also, the anodic process was found to be more efficient with C felt as the anode, and in a mixture of 1:1 methanol/acetonitrile co-solvents.
- Golub, Tatiana,Becker, James Y.
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p. 861 - 868
(2018/04/30)
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- Palladium-Catalyzed Direct Synthesis of Phenanthridones from Benzamides through Tandem N–H/C–H Arylation
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We report a palladium-catalyzed method for the direct synthesis of phenanthridones from benzamides in a single step. Unlike previous reports, the current protocol does not need any directing groups or any harsh conditions. This methodology has a wide functional group tolerance therefore a series of phenanthridones were synthesized with a yield up to 87 %. The efficacy of this protocol was further explored by synthesizing some important naturally occurring amaryllidaceae alkaloids in a single step with very good yields.
- Banerji, Biswadip,Chatterjee, Satadru,Chandrasekhar,Nayan, Chinmay,Killi, Sunil Kumar
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supporting information
p. 5214 - 5218
(2017/09/29)
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- Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives
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The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.
- Yuan, Yu-Chao,Kamaraj, Raghu,Bruneau, Christian,Labasque, Thierry,Roisnel, Thierry,Gramage-Doria, Rafael
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supporting information
p. 6404 - 6407
(2017/12/08)
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- Structure-property relationships of aromatic polyamides and polythioamides: comparative consideration with those of analogous polyesters, polythioesters and polydithioesters
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Conformational characteristics and configurational properties of aromatic polyamides and polythioamides, analogues of common aromatic polyesters such as poly(ethylene terephthalate) and poly(trimethylene terephthalate), have been investigated via NMR experiments and molecular orbital calculations on model compounds, and the refined rotational isomeric state calculations for the polymers. The polyamides and polythioamides were actually synthesized and characterized in terms of solubility, molecular weight, crystallinity, thermal transition, and thermal stability. Herein, the experimental results are discussed mainly from the viewpoint of the conformational characteristics and compared with those obtained from analogous aromatic polyesters, polythioesters, and polydithioesters to reveal the effects of the heteroatoms O, S, and NH included in the backbone on the polymer structures and properties.
- Nagasawa, Masayuki,Ishii, Tatsuya,Abe, Daisuke,Sasanuma, Yuji
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p. 96611 - 96622
(2015/11/24)
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- One-step synthesis of dicarboxamides through Pd-catalysed aminocarbonylation with diamines as N-nucleophiles
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An efficient one-step synthetic strategy was used to prepare a set of dicarboxamides through palladium-catalysed aminocarbonylation of iodoalkenyl and iodoaryl compounds, with use of various alkyl- and aryldiamines as N-nucleophiles. The isolated yields of the dicarboxamides depended significantly on the iodo substrate and diamine structures, as well as on the reaction conditions, the best one (ca. 70%) being achieved with 1-iodocyclohexene as substrate and 1,4-diaminobutane as nucleophile, at 100°C and 30 bar of CO. When iodobenzene was used as model aryl halide, the highest yield of the target dibenzamides (ca. 65%) was obtained with 1,4-diaminobenzene as coupling amine, at 100°C and 10 bar of CO. Preliminary studies on their in vitro cytotoxicity against human lung carcinoma A549 cells showed N,N′(butane-1,4-diyl)dibenzamide and androst-16-ene-based dicarboxamides to be the most efficient cytotoxic agents, with IC50 values of approximately 40 μM.
- Carrilho, Rui M.B.,Almeida, Ana R.,Kiss, Mercédesz,Kollár, László,Skoda-F?ldes, Rita,D?browski, Janusz M.,Moreno, Maria José S.M.,Pereira, Mariette M.
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supporting information
p. 1840 - 1847
(2015/05/27)
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- Synthesis and evaluation of hexahydropyrimidines and diamines as novel hepatitis C virus inhibitors
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In order to identify novel anti-hepatitis C virus (HCV) agents we devised cell-based strategies and screened phenotypically small molecule chemical libraries with infectious HCV particles, and identified a hit compound (1) containing a hexahydropyrimidine (HHP) core. During our cell-based SAR study, we observed a conversion of HHP 1 into a linear diamine (6), which is the active component in inhibiting HCV and exhibited comparable antiviral activity to the cyclic HHP 1. In addition, we engaged into the biological characterization of HHP and demonstrated that HHP does not interfere with HCV RNA replication, but with entry and release of viral particles. Here we report the results of the preliminary SAR and mechanism of action studies with HHP.
- Hwang, Jong Yeon,Kim, Hee-Young,Jo, Suyeon,Park, Eunjung,Choi, Jihyun,Kong, Sunju,Park, Dong-Sik,Heo, Ja Myung,Lee, Jong Seok,Ko, Yoonae,Choi, Inhee,Cechetto, Jonathan,Kim, Jaeseung,Lee, Jinhwa,No, Zaesung,Windisch, Marc Peter
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p. 315 - 325
(2013/11/19)
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- Efficient and continuous monoacylation with superior selectivity of symmetrical diamines in microreactors
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Efficient and continuous monoacylation of symmetrical diamines performed in microreactors yielded superior selectivity to that predicted by statistical considerations. It is highly valuable that the kinetically controlled product in high yields was achieved without any special catalyst at ambient temperature.
- Maurya, Ram Awatar,Hoang, Phan Huy,Kim, Dong-Pyo
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scheme or table
p. 65 - 68
(2012/03/26)
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- Inclusion compound of β-cyclodextrin with binuclear guests containing residues of some pharmocologically important aromatic monocarboxylic acids
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Stable monomeric and dimeric inclusion compounds of β-cyclodextrin with binuclear guests containing the residues of some pharmacologically important aromatic monocarboxylic acids were obtained. Pleiades Publishing, Ltd., 2011.
- Grachev,Charaev,Kurochkina,Batalova,Soboleva,Vasyanina,Nifant'ev
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experimental part
p. 2129 - 2135
(2012/03/12)
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- Stabilized well-dispersed Pd(0) nanoparticles for aminocarbonylation of aryl halides
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Well-dispersed palladium (0) nanoparticles stabilized with phosphonium based ionic liquid were synthesized conveniently and fully characterized. A catalyst system comprising of the Pd(0) nanoparticles and a base was found to be recyclable and efficient for the aminocarbonylation reaction of aryl iodide in ionic liquid media. In the presence of potassium tert-butyloxide, for the relatively stable aryl chloride and bromide substrates, medium activities were achieved for the catalyst. The catalyst composites can be recycled at least five times with sustained activity.
- Zhu, Yinghuai,Chuanzhao, Li,Biying, Algin Oh,Sudarmadji, Meriska,Chen, Anqi,Tuan, Dang Thanh,Seayad, Abdul M
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supporting information; experimental part
p. 9320 - 9325
(2011/10/31)
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- Imidazole-catalyzed monoacylation of symmetrical diamines
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Figure Presented. An imidazole-catalyzed protocol for monoacylation of symmetrical diamines has been developed. The protocol gave selective monoacylation of aliphatic (cyclic and acyclic) primary and secondary diamines. In the reaction, imidazole acts as both catalyst and a leaving group. Different monoacylated piperazines and other diamines were synthesized at room temperature in an ethanol/water solvent system.
- Verma, Sanjeev K.,Acharya,Kaushik
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supporting information; experimental part
p. 4232 - 4235
(2010/11/04)
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- 3,6-Dibenzoxyl-1,2-pyridazine: A new versatile benzoyl transferring agent for NH2, -OH and -SH benzoylations
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A newly synthesized 3,6-dibenzoxyl-1,2-pyridazine 3 has been investigated for its potential to transfer the benzoyl group to various organic substrates carrying -NH2, -OH and -SH groups. The benzoyl transfer is fairly general in scope, occurs under convenient conditions and provides good to excellent yields of benzoylated products. Moreover, by choosing proper conditions, it is possible to achieve chemoselective benzoylation in bi-functional molecules. For instance, N-benzoylation of aromatic amines can be selectively accomplished over that of aliphatic amines and vice versa by manipulating reaction conditions. Selective N- or O-benzoylation in aminophenols is also possible. Although, not studied in detail, we final that dibenzoate 3 can also be used to effect C-benzoylation of reactive phenols and ketones, as exemplified by the C-benzoylation of resorcinol and acetophenone, respectively. Dibenzoate 3, besides being a crystalline, easy to handle, solid possesses twice the potential as an acyl carrier compared to the other known acyl carriers. These features make 3 as an attractive choice for many applications pertaining to benzoyl transfer reactions.
- Mashraqui, Sabir Hussain,Shivaji, Jadhav Latika
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p. 927 - 935
(2007/10/03)
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- Selective Monoacylation of Symmetrical Diamines via Prior Complexation with Boron
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(Equation presented) Pretreatment of a symmetrical primary or secondary diamine with 9-BBN prior to the addition of an acyl chloride significantly suppressed undesired diacylation, and the product of monoacylation predominated. The reactive preference is interpreted as the result of a selective deactivation of one nitrogen atom of the diamine by 9-BBN.
- Zhang, Zhongxing,Yin, Zhiwei,Meanwell, Nicholas A.,Kadow, John F.,Wang, Tao
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p. 3399 - 3402
(2007/10/03)
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- Chiral phosphinamides: New catalysts for the asymmetric reduction of ketones by borane
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We have identified a new class of catalysts for the asymmetric reduction of prochiral ketones by borane. Key to the architecture of effective catalysts is an N-P=O structural unit which may be part of a phosphinamide, phosphonamide or a related structure.
- Burns, Barry,King, N. Paul,Tye, Heather,Studley, John R.,Gamble, Mark,Wills, Martin
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p. 1027 - 1038
(2007/10/03)
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- N,N'-Doacylated imidazolidines and hexahydropyrimidines
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A method for the preparation of N-monoacyl imidazolidines and hexahydropyrimidines (as hydrochlorides) by interaction of monoacylated derivatives of ethylenediamine and trimethylethylenediamine with chloromethyl methyl ether was developed.Also a method for the preparation of N,N'-diacylimidazolidines and hexahydropyrimidines either by acylation of their monoacyl derivatives or by reaction of the corresponding N,N'-diacyl alkylenediamine derivatives with dimethoxymethane, diacetoxymethane, 1,3,5-trioxane or chloromethyl methyl ether was designed. - Key words: N-mono- and N,N'-diacylated imidazolidines, N-mono- and N,N'-diacylated hexahydropyrimidines, N,N'-diacylated alkylenediamines, acylation, methylation, cyclization.
- Luk'yanov, O. A.,Pokhvisneva, G. V.,Ternikova, T. V.
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p. 1376 - 1380
(2007/10/02)
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- SYNTHESIS OF 2-ALKYLPYRIMIDINES VIA 2-ALKYL-1,4,5,6-TETRAHYDROPYRIMIDINES
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The condensation of 1,3-diaminopropane with alkanoic acids gives 2-alkyl-1,4,5,6-tetrahydropyrimidines.Dehydrogenation of the tetrahydropyrimidine derivatives over a palladium catalyst produces the 2-alkylpyrimidines in high yields.
- Pews, Richard Garth
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p. 1867 - 1872
(2007/10/02)
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- ROTATION ISOMERISM OF N,N'-DIMETHYL-α,ω-BIS(BENZOYLAMINO)ALKANES
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The kow-temperature 1H n.m.r. spectra of PhCON(Me)(CH2)nN(Me)COPh show four signals for ht e methyl groups when n 3, which are atributable to the presence of three rotational isomers.Only one isomer was detectable over a wide temperature range when n
- Cirrincione, Girolamo,Hinz, Werner,Jones, R. Alan
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p. 1089 - 1092
(2007/10/02)
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- Dynamic Protection of Amines using 18-Crown-6
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The regioselectivity of diamine monoacylation has been controlled by selective complexation with 18-crown-6 and a proton source.
- Barrett, Anthony G. M.,Lana, J. Carlos A.,Tograie, Shahrzad
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p. 300 - 301
(2007/10/02)
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