- A simple general method for conversion of functionalized esters to functionalized amides
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An efficient and easy new method for the conversion of amino-esters into amino-amides is described. In a one pot reaction between dialkyllithium amide and some amino-esters of thiophene and benzene, the corresponding amino-N-dialkylamides have been synthesized in high yields. The method was extended to malonic and phenylacetic esters. The reaction mechanism involves an anionic intermediate characterized by germylation.
- Riviere-Baudet,Morere,Dias
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Read Online
- One-pot synthesis of a highly disperse core-shell CuO-alginate nanocomposite and the investigation of its antibacterial and catalytic properties
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In this study, sodium alginate was extracted from Sargassum algae, collected from coastal waters of Bushehr, Persian Gulf, Iran and used as a stabilizing and wrapping agent for CuO nanoparticles. The synthesized nanocomposite was characterized by some spectroscopic and microscopic techniques, such as IR, XRD, Uv-vis, BET, BJH, zeta potential, SEM, TEM, HR-TEM, and XPS. The antibacterial effects of the CuO-alginate nanocomposite against some bacteria, isolated from a burn wound, were evaluated. The results showed that this nanocomposite had better antibacterial effects than its components onPseudomonas aeruginosaATCC 27853,Staphylococcus aureusATCC 12600,Streptococcus pyogenesATCC 19615, andStaphylococcus epidermidisATCC 49461. Among these,Staphylococcus aureusATCC 12600 was the most sensitive one to this nanocomposite, with the lowest minimum inhibitory concentration (2.08 mg mL?1) observed. Moreover, the synthesized nanocomposite showed good catalytic activity in the oxidative coupling of carboxylic acids withN,N-dialkylformamides toward the synthesis of amides.
- Habibi, Hassan,Mansourinejhad, Sanam,Saberi, Dariush,Shadi, Ahmad
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p. 199 - 211
(2021/12/30)
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- STRIGOLACTONE ANALOGS AND METHODS OF USING
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Disclosed herein are compounds of Formula I and methods for regulating plant growth and/or combating root parasitic plants. Formulations containing one or more disclosed compounds or salts thereof, and one or more excipients are disclosed. Methods for reg
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Page/Page column 50; 51
(2021/06/04)
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- A scalable continuous photochemical process for the generation of aminopropylsulfones
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An efficient continuous photochemical process is presented that delivers a series of novel γ-aminopropylsulfones via a tetrabutylammonium decatungstate (TBADT) catalysed HAT-process. Crucial to this success is the exploitation of a new high-power LED emitting at 365 nm that was found to be superior to an alternative medium-pressure Hg lamp. The resulting flow process enabled the scale-up of this transformation reaching throughputs of 20 mmol h-1 at substrate concentrations up to 500 mM. Additionally, the substrate scope of this transformation was evaluated demonstrating the straightforward incorporation of different amine substituents as well as alkyl appendages next to the sulfone moiety. It is anticipated that this methodology will allow for further exploitations of these underrepresented γ-aminopropylsulfone scaffolds in the future. This journal is
- Baumann, Marcus,Bonciolini, Stefano,Di Filippo, Mara
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supporting information
p. 9428 - 9432
(2020/12/15)
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- Ni-Catalyzed Regiodivergent and Stereoselective Hydroalkylation of Acyclic Branched Dienes with Unstabilized C(sp3) Nucleophiles
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Two complementary regiodivergent [(P,N)Ni]-catalyzed hydroalkylations of branched dienes are reported. When amides are employed as unstabilized C(sp3) nucleophiles, a highly regioselective 1,4-addition process is favored. The addition products are obtained in high yield and with excellent stereocontrol of the internal olefin. With use of a chiral ligand and imides as carbon nucleophiles, a 3,4-addition protocol was developed, enabling construction of two contiguous tertiary stereocenters in a single step with moderate to high levels of diastereocontrol and excellent enantiocontrol. Both methods operate under mild reaction conditions, display a broad scope, and show excellent functional group tolerance. The synthetic potential of the 3,4-hydroalkylation reaction was established via a series of postcatalytic modifications.
- Shao, Wen,Besnard, Céline,Guénée, Laure,Mazet, Clément
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supporting information
p. 16486 - 16492
(2020/10/26)
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- Direct synthesis of amides from nonactivated carboxylic acids using urea as nitrogen source and Mg(NO3)2or imidazole as catalysts
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A new method for the direct synthesis of primary and secondary amides from carboxylic acids is described using Mg(NO3)2·6H2O or imidazole as a low-cost and readily available catalyst, and urea as a stable, and easy to manipulate nitrogen source. This methodology is particularly useful for the direct synthesis of primary and methyl amides avoiding the use of ammonia and methylamine gas which can be tedious to manipulate. Furthermore, the transformation does not require the employment of coupling or activating agents which are commonly required.
- Blacker, A. John,Chhatwal, A. Rosie,Lomax, Helen V.,Marcé, Patricia,Williams, Jonathan M. J.
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p. 5808 - 5818
(2020/06/21)
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- Rh(III)-Catalyzed Distal C-H Alkenylation of Weakly Coordinating Acetamides Via Desilylation Pathway
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Rh(III)-Catalyzed distal ortho-C?H alkenylation of arylacetamides have been reported employing acetamide, a weak coordinating group, as a directing group. This challenging C?H alkenylation of arylacetamides has been achieved by using arylalkynyl silanes as a surrogate for terminal alkynes under redox neutral process through desilylation pathway. The control experiments suggest that the in situ generatedRh-species is likely to be Lewis acidic, which is playing a vital role in the desilylation step. (Figure presented.).
- Ramesh, Vinay Bapu,Muniraj, Nachimuthu,Prabhu, Kandikere Ramaiah
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supporting information
p. 3683 - 3688
(2019/07/12)
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- Structure–Activity Relationships of 1-Benzoylazulenes at the OX1 and OX2 Orexin Receptors
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We previously demonstrated the potential of di- or trisubstituted azulenes as ligands (potentiators, weak agonists, and antagonists) of the orexin receptors. In this study we investigated 27 1-benzoylazulene derivatives, uncovering seven potentiators of t
- Turku, Ainoleena,Leino, Teppo O.,Karhu, Lasse,Yli-Kauhaluoma, Jari,Kukkonen, Jyrki P.,Wallén, Erik A. A.,Xhaard, Henri
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p. 965 - 981
(2019/04/10)
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- An Efficient One–pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides
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A Mo(CO)6 (molybdenumhexacarbonyl) catalyzed reductive functionalization of amides to afford 5-amino substituted 4,5-dihydroisoxazoles is presented. The reduction of amides generates reactive enamines, which upon the addition of hydroximinoyl chlorides and base undergoes a 1,3-dipolar cycloaddition reaction that gives access to the desired heterocyclic compounds. The transformation of amides is highly chemoselective and tolerates functional groups such as nitro, nitriles, esters, and ketones. Furthermore, a versatile scope of 4,5-dihydroisoxazoles derived from a variety of hydroximinoyl chlorides and amides is demonstrated. (Figure presented.).
- Slagbrand, Tove,Kervefors, Gabriella,Tinnis, Fredrik,Adolfsson, Hans
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supporting information
p. 1990 - 1995
(2017/06/09)
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- Facile preparation of pyrimidinediones and thioacrylamides: Via reductive functionalization of amides
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The development of an efficient protocol for the reductive functionalization of amides into pyrimidinediones and amino-substituted thioacrylamides is presented. Enamines are generated in a highly chemoselective amide hydrosilylation reaction catalyzed by
- Trillo, Paz,Slagbrand, Tove,Tinnis, Fredrik,Adolfsson, Hans
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supporting information
p. 9159 - 9162
(2017/08/17)
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- Facile Access to Amides from Oxygenated or Unsaturated Organic Compounds by Metal Oxide Nanocatalysts Derived from Single-Source Molecular Precursors
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Oxidative amidation is a valuable process for the transformation of oxygenated organic compounds to valuable amides. However, the reaction is severely limited by the use of an expensive catalyst and limited substrate scope. To circumvent these limitations, designing a transition-metal-based nanocatalyst via more straightforward and economical methodology with superior catalytic performances with broad substrate scope is desirable. To resolve the aforementioned issues, we report a facile method for the synthesis of nanocatalysts NiO and CuO by the sol-gel-assisted thermal decomposition of complexes [Ni(hep-H)(H2O)4]SO4 (SSMP-1) and [Cu(μ-hep)(BA)]2 (SSMP-2) [hep-H = 2-(2-hydroxylethyl)pyridine; BA = benzoic acid] as single-source molecular precursors (SSMPs) for the oxidative amidation of benzyl alcohol, benzaldehyde, and BA by using N,N-dimethylformamide (DMF) as the solvent and as an amine source, in the presence of tert-butylhydroperoxide (TBHP) as the oxidant, at T = 80 °C. In addition to nanocatalysts NiO and CuO, our previously reported Co/CoO nanocatalyst (CoNC), derived from the complex [CoII(hep-H)(H2O)4]SO4 (A) as an SSMP, was also explored for the aforementioned reaction. Also, we have carefully investigated the difference in the catalytic performance of Co-, Ni-, and Cu-based nanoparticles synthesized from the SSMP for the conversion of various oxygenated and unsaturated organic compounds to their respective amides. Among all, CuO showed an optimum catalytic performance for the oxidative amidation of various oxygenated and unsaturated organic compounds with a broad reaction scope. Finally, CuO can be recovered unaltered and reused for several (six times) recycles without any loss in catalytic activity.
- Mohammad, Akbar,Chandra, Prakash,Ghosh, Topi,Carraro, Mauro,Mobin, Shaikh M.
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supporting information
p. 10596 - 10608
(2017/09/12)
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- Charge-Transfer Complex Promoted C-N Bond Activation for Ni-Catalyzed Carbonylation
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A new strategy was developed for activation of C-N bond via formation of an amine-I2 charge-transfer complex, which facilitates the inert C-N bond activation via oxidative addition with Ni(0). This strategy has been successfully applied in the Ni-catalyzed carbonylation of benzylamines via direct insertion of CO into the C-N bond, which provided a straightforward and rapid approach to arylacetamides in the presence of catalytic amounts of I2 and Ni catalyst. Mechanistic studies suggested that a benzyl radical generated via the oxidative addition was involved in the present reaction.
- Yu, Hui,Gao, Bao,Hu, Bin,Huang, Hanmin
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supporting information
p. 3520 - 3523
(2017/07/17)
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- Pd-Catalyzed Site-Selective p-Hydroxyphenyloxylation of Benzylic α-C(sp3)-H Bonds with 1,4-Benzoquinone
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A Pd-catalyzed, site-selective p-hydroxyphenyloxylation of benzylic α-C(sp3)-H bonds with 1,4-benzoquinone using thioamide as a directing group is reported. 1,4-Benzoquinone is employed as the p-hydroxyphenyloxy source without extra oxidants. T
- Song, Guangjun,Zheng, Ziwei,Wang, Yanhui,Yu, Xinhong
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supporting information
p. 6002 - 6005
(2016/12/09)
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- Catalytic Enantioselective α-Fluorination of 2-Acyl Imidazoles via Iridium Complexes
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The first highly enantioselective α-fluorination of 2-acyl imidazoles utilizing iridium catalysis has been accomplished. This transformation features mild conditions and a remarkably broad substrate scope, providing an efficient and highly enantioselective approach to obtain a wide range of fluorine-containing 2-acyl imidazoles which are found in a variety of bioactive compounds and prodrugs. A large scale synthesis has also been tested to demonstrate the potential utility of this fluorination method.
- Xu, Guo-Qiang,Liang, Hui,Fang, Jie,Jia, Zhi-Long,Chen, Jian-Qiang,Xu, Peng-Fei
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supporting information
p. 3355 - 3358
(2016/12/09)
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- TBAI-catalyzed synthesis of α-ketoamides via sp3 C-H radical/radical cross-coupling and domino aerobic oxidation
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A TBAI-catalyzed one-pot synthesis of α-ketoamides via sp3 C-H radical/radical cross-coupling and domino aerobic oxidation was developed. This synthesis is suitable for abroad range of substrates. The control experiments suggested a possible oxidative coupling mechanism.
- Fan, Weizheng,Shi, Dongyang,Feng, Bainian
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p. 4638 - 4641
(2015/07/02)
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- A general and practical palladium-catalyzed direct a-arylation of amides with aryl halides
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An efficient system for the direct catalytic intermolecular α-arylation of acetamide derivatives with aryl bromides and chlorides is presented. The palladium catalyst is supported by Kwong's indolebased phosphine ligand and provides monoarylated amides in up to 95% yield. Excellent chemoselectivities (>10:1) in the mono- and diarylation with aryl bromides were achieved by careful selection of bases, solvents, and stoichiometry. Under the coupling conditions, the weakly acidic α-protons of amides (pK a up to 35) were reversibly depotonated by lithium tert-butoxide (LiO-t-Bu), sodium tert-butoxide (NaO-t-Bu) or sodium bis(trimethylsilyl)amide [NaN(SiMe3)2].
- Zheng, Bing,Jia, Tiezheng,Walsh, Patrick J.
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supporting information
p. 165 - 178
(2014/03/21)
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- Carbonylation of quaternary ammonium salts to tertiary amides using NaCo(CO)4 catalyst
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We reported here the catalytic carbonylation of quaternary ammonium salts under anhydrous condition. Quaternary ammonium salts, a kind of versatile reagents that were widely used in organometallic chemistry, can be carbonylated to tertiary amides by an in situ prepared NaCo(CO)4 catalyst. It was found that the counterions (Cl-, Br-, I-, OTf-) in the quaternary ammonium salts played a significant role in the reaction and tetramethylammonium iodide could give high yield (96%) of N,N-dimethylacetamide (DMAc) with only 0.5 mol% cobalt catalyst. Under optimum conditions, several other quaternary ammonium iodides were also carbonylated to corresponding tertiary amides in moderate to excellent yields. Obviously, these results also give us a special apprehension that Me4NI and other quaternary ammonium salts could be possibly carbonylated to tertiary amides in the carbonylation reaction where they are used as promoters or solvents in most cases. Considering the high activity and moderate to excellent selectivity, this process could be a potential method for the synthesis of certain tertiary amides. Moreover, the cleaving mechanism of CN bonds and the possible catalytic intermediates were discussed in detail.
- Lei, Yizhu,Zhang, Rui,Wu, Qing,Mei, Hui,Xiao, Bo,Li, Guangxing
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p. 120 - 125
(2013/12/04)
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- Ketene reactions with tertiary amines
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Tertiary amines react rapidly and reversibly with arylketenes in acetonitrile forming observable zwitterions, and these undergo amine catalyzed dealkylation forming N,N-disubstituted amides. Reactions of N- methyldialkylamines show a strong preference for methyl group loss by displacement, as predicted by computational studies. Loss of ethyl groups in reactions with triethylamine also occur by displacement, but preferential loss of isopropyl groups in the phenylketene reaction with diisopropylethylamine evidently involves elimination. Quinuclidine rapidly forms long-lived zwitterions with arylketenes, providing a model for catalysis by cinchona and related alkaloids in stereoselective additions to ketenes.
- Allen, Annette D.,Andraos, John,Tidwell, Thomas T.,Vukovic, Sinisa
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supporting information
p. 679 - 685
(2014/04/03)
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- Copper catalyzed cross-coupling reactions of carboxylic acids: An expedient route to amides, 5-substituted γ-lactams and α-acyloxy esters
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A convenient and recyclable catalytic protocol for the synthesis of N,N-dimethyl substituted amides, 5-substituted γ-lactams and α-acyloxy ethers from carboxylic acids using CuO nanoparticles and TBHP is described.
- Priyadarshini,Amal Joseph,Lakshmi Kantam
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p. 18283 - 18287
(2013/10/21)
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- Direct synthesis of amides from carboxylic acids and amines using B(OCH2CF3)3
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B(OCH2CF3)3, prepared from readily available B2O3 and 2,2,2-trifluoroethanol, is as an effective reagent for the direct amidation of a variety of carboxylic acids with a broad range of amines. In most cases, the amide products can be purified by a simple filtration procedure using commercially available resins, with no need for aqueous workup or chromatography. The amidation of N-protected amino acids with both primary and secondary amines proceeds effectively, with very low levels of racemization. B(OCH2CF3)3 can also be used for the formylation of a range of amines in good to excellent yield, via transamidation of dimethylformamide.
- Lanigan, Rachel M.,Starkov, Pavel,Sheppard, Tom D.
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p. 4512 - 4523
(2013/06/05)
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- Direct catalytic formation of primary and tertiary amides from non-activated carboxylic acids, employing carbamates as amine source
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The operationally simple titanium(IV)- or zirconium(IV)-catalyzed direct amidation of non-activated carboxylic acids with ammonium carbamates generates primary, and tertiary N,N-dimethyl-substituted amides in good to excellent yields. Copyright
- Tinnis, Fredrik,Lundberg, Helena,Adolfsson, Hans
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supporting information
p. 2531 - 2536
(2012/11/06)
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- Utility of dysprosium as a reductant in coupling reactions of acyl chlorides: The synthesis of amides and diaryl-substituted acetylenes
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Reduction of acyl chlorides with dysprosium metal has been studied. The reducing ability of dysprosium metal is solvent-dependent. Dysprosium metal, which requires neither any additive nor pretreatment, can promote the cross-coupling of acyl chlorides in DMF or DEF to give amides in good yields. When the reaction was performed in N,N-dimethylacetamide, the reductive self-coupling reaction of aroyl chloride took place smoothly and afforded the diaryl-substituted acetylenes in moderate to good yield.
- Chen, Weifeng,Li, Kebin,Hu, Ziqiang,Wang, Liliang,Lai, Guoqiao,Li, Zhifang
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scheme or table
p. 2026 - 2030
(2011/06/18)
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- Oxidative C-H homodimerization of phenylacetamides
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A range of secondary and tertiary phenylacetamides undergo oxidative homodimerization to afford biaryls. The reaction proceeds under palladium catalysis in the presence of a copper cocatalyst and oxygen and is most effective for electron-rich substrates.
- Pintori, Didier G.,Greaney, Michael F.
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supporting information; experimental part
p. 5713 - 5715
(2011/12/04)
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- Pd(II)-catalyzed synthesis of indoles from α-aryloxime O-pentafluorobenzoates via intramolecular aromatic C-H amination
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α-Aryl-a-aminocarbonyloxime O-pentafluorobenzoates are found to be promising precursors for synthesis of 2 3-disubstituted indole derivatives catalyzed by PdCl2(MeCN)2 in the presence of MgO as a base. The reaction is supposed to pro
- Chiba, Shunsuke,Zhang, Line,Sanjaya, Stephen,Ang, Gim Yean
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experimental part
p. 5692 - 5700
(2010/10/02)
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- PROCESS FOR PREPARING SECONDARY AMIDES BY CARBONYLATION OF A CORRESPONDING TERTIARY AMINE
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The present invention relates to a process for preparing secondary amides with good selectivity by carbonylating a corresponding tertiary amine with carbon monoxide in a reaction mixture in the presence of a metal catalyst and in the presence of a halogen containing promoter. The metal catalyst comprises palladium. A same or even a much better catalytic activity can be obtained with palladium than with the much more expensive rhodium, especially when the palladium is used in a low concentration. Moreover, also a good selectivity can be achieved.
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Page/Page column 4
(2010/06/14)
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- Palladium-catalyzed conversion of benzylic and allylic halides into α-aryl and β,γ-unsaturated tertiary amides by the use of a carbamoylsilane
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Treatment of allylic and benzylic halides with N,N- dimethylcarbamoyl(trimethyl)silane in the presence of tetrakis- (triphenylphosphine)palladium(0) affords tertiary amides, which arise from the replacement of the halogen by the N,N-dimethylcarbamoyl group.
- Cunico, Robert F.,Pandey, Rajesh K.
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p. 9048 - 9050
(2007/10/03)
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- The extraordinary reactions of phenyldimethylsilyllithium with N,N-disubstituted amides
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The reactions of the silyllithium reagent with tertiary amides was discussed. The enediamines were easily isomerized from cis to trans, easily oxidized to dienediamines and were hydrolyzed to α-aminoketones. If the two equivalents of the silyllithium reagent were used, the product was an α-silylamine. The results show that each member of the homologous series of amides gives rise to a substantially different product.
- Buswell, Marina,Fleming, Ian,Ghosh, Usha,Mack, Stephen,Russell, Matthew,Clark, Barry P.
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p. 3006 - 3017
(2007/10/03)
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- C-H insertion approach to the synthesis of endo,exo-furofuranones: Synthesis of (±)-asarinin, (±)-epimagnolin A, and (±)-fargesin
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A series of novel 5-aryl-4-aryloxymethyl-3-diazotetrahydrofuran-2-ones (12, 24, and 35a/b) have been prepared and found to undergo regio- and stereoselective C-H insertion reactions to afford 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane-8-ones (18, 26, and 36a/b) with endo,exo stereochemistry. Subsequent reduction of the lactone ring and cyclization of the resulting diols 27 and 37a/b permitted the synthesis of three endo, exo-furofuran lignans: asarinin (2), fargesin (3), and epimagnolin A (4). En route to the key diazo compounds 24 and 35a/b, a modified procedure for the Ghosez keteniminium-olefin cyclization was developed, which was required to minimize the decomposition of acid-sensitive functional groups such as electron-rich benzylic ethers that were present in the target compounds 2-4.
- Brown,Bataille,Bruton,Hinks,Swain
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p. 6719 - 6728
(2007/10/03)
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- A novel method for the mild and selective amidation of diesters and the amidation of monoesters
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The selective monoamidation of diesters and amidation of esters mediated by Lewis acids are described. The selective amidations of dimethyl pyridine-2,5-dicarboxylate (1) and dimethyl 2,3-indole-dicarboxylate (4) with primary and secondary amines mediated
- Guo, Zhenrong,Dowdy, Eric D.,Li, Wen-Sen,Polniaszek, Richard,Delaney, Edward
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p. 1843 - 1845
(2007/10/03)
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- Heterocyclic compounds, their production and use
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A novel compound of the formula: wherein A is a condensed pyrimidinone or condensed pyridazinone ring; Ar1 and Ar2 are independently a ring; Z is a divalent group, or a salt thereof which have an excellent antitumor activity.
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- Oxidation of benzylamines to amides
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A convenient method for the conversion of tertiary benzylamines to benzamides by phase transfer oxidation is described. Yields are good. Regioselectivities are reported.
- Markgraf, J. Hodge,Sangani, Poorab K.,Finkelstein, Manuel
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p. 1285 - 1290
(2007/10/03)
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- Substituent Effects on the CC Bond Strength, 17. - Formation and Stability of α-Carbamoylbenzyl Radicals
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Products and kinetics of the homolytic thermolyses reactions of the three tertiary amides 6a-c of 2,3,3-triphenylpropanoic acid were studied in solution.The steric effects on the C-C bond homolysis processes were evaluated from MM2 calculations.Taking this into account, we deduced radical stabilization enthalpies RSE for the α-carbamoylbenzyl radicals 3a-c from the activation enthalpies ΔH(excit.) . - Key Words: Bond cleavage, C-C kinetics of / Radicals, stability of
- Zueffle, Stephan,Beckhaus, Hans-Dieter,Ruechardt, Christoph
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p. 877 - 880
(2007/10/02)
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- Synthesis of N,N-dimethyl α-aryl and α,α-diarylacetamides by radical nucleophilic substitution reactions
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A family of N,N-dimethyl, α-aryl and α,α-diaryl acetamides was synthesized by reaction of aryl halides with N,N-dimethyl acetamide enolate ions in liquid ammonia.The reactions followed the SRN1 mechanism for nucleophilic substitution.They were initiated by light (350 nm), when the aryl halides or aryl halides bearing electron-donating groups were the substrate, and by potassium metal dissolved in liquid ammonia when the substituents on the aryl halides were electron-withdrawing groups. Key Words: SRN1 / nucleophilic substitution / synthesis / acetamide compounds / herbicides
- Palacios, S. M.,Asis, S. E.,Rossi, R. A.
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p. 111 - 116
(2007/10/02)
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- A Novel Series of N-(1-Aminoalkylidene)carboximidamides as Potential Hypoglycemic Agents
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Nitrogen heterocyclic carboximidamides, such as linogliride, 1a, have been shown to possess significant hypoglycemic activity and have shown clinical efficacy as potential antidiabetic agents.We evaluated the biological significance of the heterocyclic ring A of general structure 1, which has always been maintained in this class of compounds, by preparing acyclic compounds of general structure 2.Preliminary in vivo biological testing, i.e., the glucose tolerance test in rats, indicates that a number of the specific acyclic carboximidamides prepared, 6a-6kk, possessed significant hypoglycemic activity often comparable to, and in some cases better than, the activity noted for our model compound, 1a.These results suggest that the heterocyclic ring A of 1 is not essential for hypoglycemic activity for this class of compounds.
- Breslin, Henry J.,Kukla, Michael J.,Tuman, Robert W.,Rebarchak, Mary C.,Bowden, Charles R.
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p. 1597 - 1603
(2007/10/02)
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- 2-Phenyl-2-(1-hydroxycycloalkyl)ethylamine derivatives: Synthesis and antidepressant activity
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A series of 2-phenyl-2-(1-hydroxycycloalkyl)ethylamine derivatives was examined for the ability to inhibit both rat brain imipramine receptor binding and the synaptosomal uptake of norepinephrine (NE) and serotonin (5-HT). Neurotransmitter uptake inhibition was highest for a subset of 2-phenyl-2-(1-hydroxycyclohexyl)dimethylethylamines in which the aryl ring has a halogen or methoxy substituent at the 3- and/or 4-positions. Potential antidepressant activity in this subset was assayed in three rodent models - the antagonism of reserpine-induced hypothermia, the antagonism of histamine-induced ACTH release, and the ability to reduce noradrenergic responsiveness in the rat pineal gland. An acute effect seen in the rat pineal gland with several analogues, including 1-[1-(3,4-dichlorophenyl)-2-(dimethylamino)ethyl]cyclohexanol (23) and 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol (4), was taken as a possible correlate of a rapid onset of antidepressant activity. Compound 4 (venlafaxine) is presently undergoing clinical evaluation.
- Yardley,Morris Husbands,Stack,Butch,Bicksler,Moyer,Muth,Andree,Fletcher III,James,Sielecki
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p. 2899 - 2905
(2007/10/02)
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- AROMATIC CYCLIZATIONS OF β-AMINOETHYL RADICALS AND α-CARBAMOYLMETHYL RADICALS. ORTHO-SUBSTITUTION VS. IPSO-SUBSTITUTION
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On being treated with Bu3SnH, the N-benzyl-N-(β-bromoethyl)sulfonamide (4) underwent a homolytic ortho-substitution reaction to give the tetrahydroisoquinoline (6).In contrast, the N-arylmethyl-α-chloroacetamides (10) afforded the ipso-substitution products (11).A similar treatment of the N-naphthylmethyl derivative (16) provided the spiro-γ-lactam (17).
- Ishibashi, Hiroyuki,Nakamura, Nobuyuki,Ito, Katsuhiro,Kitayama, Shinji,Ikeda, Masazumi
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p. 1781 - 1784
(2007/10/02)
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- SYNTHESIS OF 1-(ARYLETHYNYL)AZIRIDINES
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Studies have been made on the possible synthesis of 1-(arylethynyl)aziridines by oxidative condensation of phenylacetylene with aziridine and by alkylation of aziridine with 1-halo-2-arylacetylenes.
- Tikhomirov, D. A.,Eremeev, A. V.
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- Crystal Structure and Tautomerism in 4-Phenylisoxazoles with Two Potential Hydroxyl Groups at Positions 3 and 5
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The crystal structure of 4-phenyl-3-hydroxyisoxazol-5-one semihydrate exhibits an exceptional hydrogen bonded polymeric structure with a unit cell of 8 molecules.The hydrogen bonds strech out, using the oxohydroxy groups in positions 3 and 5 in the direct
- Zvilichovsky, Gury
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p. 465 - 470
(2007/10/02)
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- Metallic Nickel-Mediated Synthesis of Ketones by the Reaction of Benzylic, Allylic, Vinylic, and Pentafluorophenyl Halides with Acid Halides
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Metallic nickel was investigated as a convenient coupling reagent for the synthesis of ketones by the reaction of benzylic, allylic, vinylic, and pentafluorophenyl halides with acid halides at 85 deg C in glyme.A variety of benzylic ketones with functional groups including halogen, cyano, methoxycarbonyl, and hydroxycarbonyl groups were prepared in good yields by this method.The reaction was demonstrated to proceed via organonickel halide intermediates formed by the smooth oxidative addition of benzylic and acyl halides to metallic nickel, which were trapped with electron-deficient olefins. (?-Allyl)nickel halides, prepared in situ at 85 deg C from allylic halides and the nickel, also worked for the preparation of ketones.Vinylic and pentafluorophenyl halides but not alkyl halides reacted with acid halides to give the corresponding ketones in moderate yields.
- Inaba, Shin-ichi,Rieke, Reuben D.
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p. 1373 - 1381
(2007/10/02)
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- AN ALTERNATIVE PROCEDURE FOR THE ALUMINUM-MEDIATED CONVERSION OF ESTERS TO AMIDES
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A convenient method has been developed for directly converting esters to amides using reagents derived from the reaction of trimethylaluminum with ammonium chloride, methylamine hydrochloride or dimethylamine hydrochloride.
- Levin, Jeremy I.,Turos, Edward,Weinreb, Steven M.
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p. 989 - 994
(2007/10/02)
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- A CONVENIENT METHOD FOR THE SYNTHESIS OF CARBOXAMIDES AND PEPTIDES BY THE USE OF TETRABUTYLAMMONIUM SALTS
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Various carboxamides and peptides are prepared in good yields by treatment of free acids and amines in H2O-dichloromethane or aqueous THF with bis(o-nitrophenyl) phenylphosphonate in the presence of tetrabutylammonium hydrogen sulfate or bromide.Carboxylic esters are also successfully converted to amides via carboxylate salts in one-pot.
- Watanabe, Yutaka,Mukaiyama, Teruaki
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p. 285 - 288
(2007/10/02)
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- Process for preparation of o-(2,6-dichloroanilino)phenylacetic acid and novel intermediate for use in preparation of the same
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Disclosed is a process for the preparation of o-(2,6-dichloroanilino)phenylacetic acid (Diclofenac) or its pharmacologically acceptable acid addition salt, which comprises hydrolyzing an N,N-disubstituted-o-(2,6-dichloroanilino)phenylacetamide derivative with an alkali. Also a novel intermediate for use in the preparation of Diclofenac, that is, an N,N-disubstituted-o-halogenophenylacetamide in which the halogen is iodine or bromine, is disclosed.
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- Photostimulated Reactions of N,N-Disubstituted Amide Enolate Anions with Haloarenes by the SRN1 Mechanism in Liquid Ammonia
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The photostimulated reactions of chloro-, bromo-, and iodobenzenes, 1-chloronaphthalene, and 9-bromophenanthrene with the enolate anion of N-methyl-N-phenylacetamide in liquid ammonia gave good yields of substituted products.In the dark, iodobenzene gave 34percent of substitution product, but chlorobenzene did not react.The enolate anion of N,N-dimethylacetamide was only partially soluble in liquid ammonia, but good yields of substitution products were obtained.The enolate anion of N-acetylpiperidine was insoluble in liquid ammonia, but the enolate anion of N-acetylmorpholine was soluble and good yields of substitution products were obtained under photostimulation.It is suggested that these reactions occur by the SRN1 mechanism of aromatic substitution.
- Rossi, Roberto A.,Alonso, Ruben A.
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p. 1239 - 1241
(2007/10/02)
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- Synthesis of α-fluorocarbonyl compounds
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Process for preparing an organic compound of the formula R2 R2 CFC(O)R3, which process comprises contacting and reacting in a reaction mixture which includes an inert solvent, at a temperature of -40° C. to -100° C., ROF and STR1 R is polyfluoroperhaloalkyl of 1-6 carbon atoms or FOCF2 ; R1 is hydrocarbyl of 1-6 carbon atoms; each R2 is selected from H, alkyl of 1-17 carbon atoms, cycloalkyl of 3-6 carbon atoms, aryl, heteroaryl and such alkyl, cycloalkyl, aryl and heteroaryl substituted by halogen or alkoxy of 1-6 carbon atoms; R3 is selected from H, alkyl and haloalkyl of 1-16 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl and haloaryl, OSi(R1)3, OH, NH2, alkoxy of 1-6 carbon atoms, aryloxy, NHR1 and NR12 wherein R1 is alkyl of 1-6 carbon atoms, N-arylamino and nitrogen or sulfur heterocyclic of 4-5 carbon atoms; R3 and one R2 taken together is a diradical which with the C=C group is carbocyclic, heterocyclic or haloheterocyclic, and recovering from the reaction mixture the compound of the formula R2 R2 CFC(O)R3.
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