- Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)
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This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.
- Brittain, William D. G.,Cobb, Steven L.
-
supporting information
p. 5793 - 5798
(2021/08/01)
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- Electron-Catalyzed Aminocarbonylation: Synthesis of α,β-Unsaturated Amides from Alkenyl Iodides, CO, and Amines
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Aminocarbonylation of alkenyl iodides with CO and amines proceeded under heating to produce α,β-unsaturated amides in good yields (23 examples, 71% average yield). This catalyst-free method exhibited good functional-group tolerance, and open a straightforward access to functionalized acrylamides, as illustrated by the synthesis of Ilepcimide. A hybrid radical/ionic mechanism involving chain electron transfer is proposed for this transformation.
- Picard, Baptiste,Fukuyama, Takahide,Bando, Takanobu,Hyodo, Mamoru,Ryu, Ilhyong
-
supporting information
p. 9505 - 9509
(2021/12/09)
-
- Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides
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Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).
- Liu, Xin,Werner, Thomas
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p. 1096 - 1104
(2020/12/31)
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- Copper(I)-Catalyzed Asymmetric 1,4-Conjugate Hydrophosphination of α,β-Unsaturated Amides
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A catalytic asymmetric conjugate hydrophosphination of α,β-unsaturated amides is accomplished by virtue of the strong nucleophilicity of copper(I)-PPh2 species, which provides an array of chiral phosphines bearing an amide moiety in high to excellent yields with excellent enantioselectivity. Furthermore, the dynamic kinetic resolution of unsymmetrical diarylphosphines (HPAr1Ar2) is successfully carried out through the copper(I)-catalyzed conjugate addition to α,β-unsaturated amides, which affords P-chiral phosphines with good-to-high diastereoselectivity and high enantioselectivity. 1H NMR studies show that the precoordination of HPPh2 to copper(I)-bisphosphine complex is critical for the efficient deprotonation by Barton's Base. Moreover, the relative stability of the copper(I)-(R,RP)-TANIAPHOS complex in the presence of excessive HPPh2, confirmed by 31P NMR studies, is pivotal for the high asymmetric induction, as the ligand exchange between bisphosphine and HPPh2 would significantly reduce the enantioselectivity. At last, a double catalytic asymmetric conjugate hydrophosphination furnishes the corresponding product in high yield with high diastereoselectivity and excellent enantioselectivity, which is transformed to a chiral pincer palladium complex in moderate yield. This chiral palladium complex is demonstrated as an excellent catalyst in the asymmetric conjugate hydrophosphination of chalcone.
- Li, Yan-Bo,Tian, Hu,Yin, Liang
-
supporting information
p. 20098 - 20106
(2021/01/01)
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- Synthesis of Cinnamides via Amidation Reaction of Cinnamic Acids with Tetraalkylthiuram Disulfides Under Simple Condition
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A facile and efficient methodology for the synthesis of cinnamides has been achieved under metal- and additive-free conditions. This method allows the efficient C–N cross-coupling of diverse cinnamic acids with tetraalkylthiuram disulfides through a simply mixing operation in 1,2-dichloroethane at 100 °C. The protocol provides a direct approach to cinnamides and is featured with readily available starting materials and broad substrate scope, which shows its practical synthetic value in organic synthesis.
- Lai, Miao,Wu, Zhiyong,Su, Fangyao,Yu, Yujian,Jing, Yanqiu,Kong, Jinmin,Wang, Zhenteng,Wang, Shuai,Zhao, Mingqin
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p. 198 - 208
(2020/01/22)
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- Palladium-Catalyzed N-Acylation of Tertiary Amines by Carboxylic Acids: A Method for the Synthesis of Amides
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A palladium-catalyzed N-acylation of tertiary amines by carboxylic acids was achieved through C-N cleavage. This reaction showed a wide substrate scope. Both aromatic and aliphatic acids served well as the acylating reagents and coupled with tertiary amines to produce the corresponding amides in good to excellent yields. With the strategy, bioactive carboxylic acids were also efficiently modified, highlighting the synthetic value of the process in organic synthesis.
- Li, Zhaohui,Liu, Long,Xu, Kaiqiang,Huang, Tianzeng,Li, Xinyi,Song, Bin,Chen, Tieqiao
-
supporting information
p. 5517 - 5521
(2020/07/14)
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- Preparation method of cinnamamide (by machine translation)
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The synthesis system disclosed by the invention has the advantages of simple :(1) reaction conditions, wide, reaction conditions, reaction conditions, wide ;(2) substrate range, high yield (1) and wide application range, and the reaction liquid, can be used as an anti-cancer drug, anti-anti-tumor and spice precursor compound in an organic solvent to prepare a corresponding cinnamide compound, product cinnamide . The synthesis system disclosed by the invention has a broad spectrum . The synthesis system disclosed by the invention has a broad spectrum of biological activity, and is suitable for popularization and application, in the following steps, synthesizing cinnamic acid and thiuram disulfide as a raw material, in an organic, solvent, and purifying, parts by mass, separation and purification of the obtained reaction, solution in an organic solvent. (by machine translation)
- -
-
Paragraph 0183-0189
(2020/05/01)
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- Visible-light-promoted oxidation/condensation of benzyl alcohols with dialkylacetamides to cinnamides
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Oxidative cross-coupling reactions of benzyl alcohols with N,N-dialkylacetamides were developed only employing oxygen as the terminal oxidant, efficiently providing a new, novel protocol for the construction of multifunctionalized cinnamides with the synergistic effects of KOH, organic photocatalyst eosin Y, and visible light irradiation at room temperature. A broad substrate scope and mild reaction conditions are the prominent features of this transformation.
- Yang, Tianlong,Lu, Maojian,Lin, Zhaowei,Huang, Mingqiang,Cai, Shunyou
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supporting information
p. 449 - 453
(2019/01/24)
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- Radical α,β-Dehydrogenation of Saturated Amides via α-Oxidation with TEMPO under Transition Metal-Free Conditions
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A transition metal-free radical process for the selective α,β-dehydrogenation of saturated amides under mild conditions is developed. Utilizing radical activation strategy, the challenging issue associated with the low α-acidity of amides is resolved. For the first time, α,β-unsaturated Weinreb amides and acrylamides could be efficiently prepared directly from corresponding saturated amides. Mechanistic studies confirm the radical nature of this transformation. Two gram scale α,β-dehydrogenation have also been performed to demonstrate the utility of this method.
- Wang, Mei-Mei,Sui, Guo-Hui,Cui, Xian-Chao,Wang, Hui,Qu, Jian-Ping,Kang, Yan-Biao
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p. 8267 - 8274
(2019/06/27)
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- Chemoselective α,β-Dehydrogenation of Saturated Amides
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We report a method for the selective α,β-dehydrogenation of amides in the presence of other carbonyl moieties under mild conditions. Our strategy relies on electrophilic activation coupled to in situ selective selenium-mediated dehydrogenation. The α,β-unsaturated products were obtained in moderate to excellent yields, and their synthetic versatility was demonstrated by a range of transformations. Mechanistic experiments suggest formation of an electrophilic SeIV species.
- Teskey, Christopher J.,Adler, Pauline,Gon?alves, Carlos R.,Maulide, Nuno
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p. 447 - 451
(2019/01/04)
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- Amidation reaction of carboxylic acid with formamide derivative using SO3?pyridine
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The amidation reaction of carboxylic acid derivatives was developed using sulfur trioxide pyridine complex (SO3?py) as a commercially available and easily handled oxidant. This method could be applied to the reaction of various aromatic and aliphatic carboxylic acids, including optically active ones, with formamide derivatives to afford the corresponding amides in good to high yields.
- Kawano, Shota,Saito, Kodai,Yamada, Tohru
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supporting information
p. 584 - 586
(2018/04/12)
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- Bioactivity and structure–activity relationship of cinnamic acid derivatives and its heteroaromatic ring analogues as potential high-efficient acaricides against Psoroptes cuniculi
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A series of cinnamic acid derivatives and its heteroaromatic ring analogues were synthesized and evaluated for acaricidal activity in vitro against Psoroptes cuniculi, a mange mite. Among them, eight compounds showed the higher activity with median lethal concentrations (LC50) of 0.36–1.07 mM (60.4–192.1 μg/mL) and great potential for the development of novel acaricidal agent. Compound 40 showed both the lowest LC50 value of 0.36 mM (60.4 μg/mL) and the smallest median lethal time (LT50) of 2.6 h at 4.5 mM, comparable with ivermectin [LC50 = 0.28 mM (247.4 μg/mL), LT50 = 8.9 h], an acaricidal drug standard. SAR analysis showed that the carbonyl group is crucial for the activity. The type and chain length of the alkoxy in the ester moiety and the steric hindrance near the ester group significantly influence the activity. The esters were more active than the corresponding thiol esters, amides, ketones or acids. Replacement of the phenyl group of cinnamic esters with α-pyridyl or α-furanyl significantly increase the activity. Thus, a series of cinnamic esters and its heteroaromatic ring analogues with excellent acaricidal activity emerged.
- Chen, Dong-Dong,Zhang, Bing-Yu,Liu, Xiu-Xiu,Li, Xing-Qiang,Yang, Xin-Juan,Zhou, Le
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p. 1149 - 1153
(2018/03/05)
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- Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines
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A reduction of various aryl, alkyl, and α,β-unsaturated amides with phenylsilane, catalysed by a borinic acid, is reported. The unprecedented reaction was carried out under very mild conditions and led to useful amines. Furthermore, the reaction tolerates a variety of functional groups. Initial investigations implicated that an intermediate diarylhydroborane is involved in the reaction mechanism.
- Chardon, Aurélien,Mohy El Dine, Tharwat,Legay, Rémi,De Paolis, Micha?l,Rouden, Jacques,Blanchet, Jér?me
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supporting information
p. 2005 - 2009
(2017/02/19)
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- Vanadium(V)-Induced Oxidative Cross-Coupling of Various Boron and Silyl Enolates
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Intermolecular oxidative cross-coupling of two different enolates is one of the most useful reactions to synthesize unsymmetrical 1,4-dicarbonyl compounds. In this study, the oxovanadium(V)-induced intermolecular oxidative cross-coupling of enolates afforded unsymmetrical 1,4-dicarbonyl compounds. Various boron and silyl enolates underwent the formation of ketone–ester, ester–ketone, ester–ester, amide–ketone and amide–ester coupling products. These results clearly show the versatility of the present oxidative cross-coupling protocol.
- Amaya, Toru,Osafune, Yuma,Maegawa, Yusuke,Hirao, Toshikazu
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p. 1301 - 1304
(2017/06/23)
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- Sunlight assisted direct amide formation: Via a charge-transfer complex
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We report on the use of charge-transfer complexes between amines and carbon tetrachloride, as a novel way to activate the amine for photochemical reactions. This principle is demonstrated in a mild, transition metal free, visible light assisted, dealkylative amide formation from feedstock carboxylic acids and amines. The low absorption coefficient of the complex allows deep light penetration and thus scale up to a gram scale.
- Cohen, Irit,Mishra, Abhaya K.,Parvari, Galit,Edrei, Rachel,Dantus, Mauricio,Eichen, Yoav,Szpilman, Alex M.
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supporting information
p. 10128 - 10131
(2017/09/23)
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- One-pot synthesis of amides from carboxylic acids activated using thionyl chloride
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A one-pot synthesis of secondary and tertiary amides from carboxylic acids and amines by using SOCl2 has been developed. Also when sterically hindered amines were used as the starting materials, excellent yields of the corresponding amides were obtained. The amidation of N-protected α-amino acids with secondary amines proceeds effectively with good yields. The process works well also in the presence of acid sensitive groups and occurs with almost complete retention of stereochemical integrity of chiral substrates. This protocol could be extended to industrial large-scale production processes.
- Leggio,Belsito,De Luca,Di Gioia,Leotta,Romio,Siciliano,Liguori
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p. 34468 - 34475
(2016/06/13)
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- Borane-Catalyzed Reductive α-Silylation of Conjugated Esters and Amides Leaving Carbonyl Groups Intact
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Described herein is the development of the B(C6F5)3-catalyzed hydrosilylation of α,β-unsaturated esters and amides to afford synthetically valuable α-silyl carbonyl products. The α-silylation occurs chemoselectively, thus leaving the labile carbonyl groups intact. The reaction features a broad scope of both acyclic and cyclic substrates, and the synthetic utility of the obtained α-silyl carbonyl products is also demonstrated. Mechanistic studies revealed two operative steps: fast 1,4-hydrosilylation of conjugated carbonyls and then slow silyl group migration of a silyl ether intermediate.
- Kim, Youngchan,Chang, Sukbok
-
supporting information
p. 218 - 222
(2016/01/25)
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- Iodobenzene Dichloride in the Esterification and Amidation of Carboxylic Acids: In-Situ Synthesis of Ph3PCl2
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A novel, in-situ synthesis of dichlorotriphenylphosphorane (Ph3PCl2) is accomplished upon combining PPh3and the easily prepared hypervalent iodine reagent iodobenzene dichloride (PhICl2). The phosphorane is selectively generated in the presence of carboxylic acid or alcohol residues to rapidly produce acyl chlorides and alkyl chlorides in high yields. Addition of EtOH, PhOH, BnOH, Et2NH or CH2N2results in the direct synthesis of esters, amides and diazo ketones from carboxylic acids.
- Carle, Myriam S.,Shimokura, Grace K.,Murphy, Graham K.
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p. 3930 - 3933
(2016/08/24)
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- Iridium(I) N-Heterocyclic Carbene (NHC)/Phosphine Catalysts for Mild and Chemoselective Hydrogenation Processes
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The directed chemoselective hydrogenation of olefins has been established by using iridium(I) catalysts, which feature a tuned NHC/phosphine ligand combination. This selective reduction process has been demonstrated in a wide array of solvents, including more environmentally acceptable media, also allowing further refinement of hydrogenation selectivity. The directed, chemoselective hydrogenation of olefins has been established by using iridium(I) catalysts, which feature a tuned NHC/phosphine ligand combination. This selective reduction process has been demonstrated in a wide array of solvents, including more environmentally acceptable media, also allowing further refinement of hydrogenation selectivity.
- Kerr, William J.,Mudd, Richard J.,Brown, Jack A.
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supporting information
p. 4738 - 4742
(2016/04/05)
-
- Synthesis of Cinnamanilide Derivatives and Their Antioxidant and Antimicrobial Activity
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The amide derivatives of cinnamic acid were synthesized and their antimicrobial and antioxidant activities were investigated. The investigation of antimicrobial potentials of the compounds demonstrated a strong activity against 21 bacterial strains comprising Gram-positive and Gram-negative bacteria. Compounds 2a, 2b, and 3b showed strong antimicrobial activity against all microorganisms with the pMIC value ranging from 2.45 to 3.68. Compounds 2a, 3a, and 3b demonstrated strong antioxidant activity with % inhibition of the DPPH radical of 51% (±1.14), 41% (±1.01), and 50% (±1.23), respectively. These findings indicate that the amide derivatives of the cinnamic acid possess strong antibacterial and antioxidant activities.
- Nimse, Satish Balasaheb,Pal, Dilipkumar,Mazumder, Avijit,Mazumder, Rupa
-
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- Tandem superelectrophilic hydroarylation of CC bond and carbonyl reduction in cinnamides: Synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals
-
Cinnamides ArCHCHCONRR′ in reactions with arenes Ar′H under the action of Bronsted (TfOH, FSO3H) or Lewis (AlBr3) superacids at rt for 1-2 h give CC bond hydroarylation products ArAr′CHCH2CONRR′ in yields of 63-98%. Reduction (LiAlH4/Et2O) of carbonyl group in the latter results in the formation of 3,3-diarylpropylamines ArAr′CHCH2CH2NRR′, valuable drugs. The reaction intermediates, superelectrophilic dications ArC+H-CH2C(OH+)NRR′, have been characterized by DFT calculations in terms of global electrophilicity index, natural charges, and atomic orbitals contributions.
- Zakusilo, Dmitry N.,Ryabukhin, Dmitry S.,Boyarskaya, Irina A.,Yuzikhin, Oleg S.,Vasilyev, Aleksander V.
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p. 102 - 108
(2015/02/02)
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- Iron-facilitated oxidative radical decarboxylative cross-coupling between α-oxocarboxylic acids and acrylic acids: An approach to α,β-unsaturated carbonyls
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The first Fe-facilitated decarboxylative cross-coupling reaction between α-oxocarboxylic acids and acrylic acids in aqueous solution has been developed. This transformation is characterized by its wide substrate scope and good functional group compatibility utilizing inexpensive and easily accessible reagents, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated carbonyls frequently found in bioactive compounds. The synthetic potential of the coupled products is also demonstrated in subsequent functionalization reactions. Preliminary mechanism studies suggest that a free radical pathway is involved in this process: the generation of an acyl radical from α-oxocarboxylic acid via the excision of carbon dioxide followed by the addition of an acyl radical to the α-position of the double bond in acrylic acid then delivers the α,β-unsaturated carbonyl adduct through the extrusion of another carbon dioxide.
- Jiang, Qing,Jia, Jing,Xu, Bin,Zhao, An,Guo, Can-Cheng
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p. 3586 - 3596
(2015/04/22)
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- Methylaluminoxane (MAO)-assisted direct amidation of esters
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Aliphatic and aromatic esters are efficiently transformed into amides in good to excellent yields, under mild conditions using methylaluminoxane (MAO). This reaction can be performed either at room temperature or by applying microwave irradiation.
- Desrat, Sandy,Ducousso, Aline,Gapil, Shelly,Remeur, Camille,Roussi, Fanny
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p. 385 - 387
(2015/02/19)
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- PhICl2 and wet DMF: An efficient system for regioselective chloroformyloxylation/a-chlorination of alkenes/a,β-unsaturated compounds
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PhICl2 in wet DMF was found to form an efficient system for realizing difunctionalization of various alkenes and olefinic derivatives possessing a wide range of functional groups. This novel methodology provides convenient access to either regioselective chloroformyloxylated products or a-chlorinated olefinic products, depending on the type of structure of the original unsaturated starting material. The mechanism of the reaction is proposed and discussed.
- Liu, Le,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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supporting information
p. 436 - 439
(2014/04/03)
-
- Metal-free tandem oxidative aryl migration and C-C bond cleavage: Synthesis of α-ketoamides and esters from acrylic derivatives
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A novel tandem metal-free oxidative aryl migration/C-C bond-cleavage reaction, mediated by hypervalent iodine reagent, has been discovered. The presented transformation provided straightforward access to important α-ketoamide and α-ketoester derivatives from readily available acrylic derivatives via a concerted process of 1,2-aryl shift concomitant with C-C bond cleavage.
- Liu, Le,Du, Liang,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
-
supporting information
p. 5772 - 5775
(2015/02/19)
-
- Silver acetate-assisted formation of amides from acyl chlorides
-
A mild method for the aminolysis of carboxylic acid chlorides to give amides is disclosed. Reactions are carried out in the presence of silver acetate in non-aqueous environments under heterogeneous phase conditions. Amides are easily recovered in very good to excellent yields and without racemization. The approach is successful in forming peptide bonds starting from N-(4-nitrobenzenesulfonyl)-amino acid chlorides and allows the formation of dipeptides also when N-methylated amino acid derivatives are used.
- Leggio,Belsito,Di Gioia,Leotta,Romio,Siciliano,Liguori
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p. 199 - 202
(2015/02/02)
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- Direct amidation of carboxylic acids with tertiary amines: Amide formation over copper catalysts through C-N bond cleavage
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A copper-catalyzed system for the amidation of carboxylic acids with tert-amines through C-N bond cleavage was developed. This protocol is practical and represents a simple way to produce functionalized amides from basic starting materials in moderate to good yields. A plausible mechanism is proposed for the reaction. Copyright
- Xiong, Biquan,Zhu, Longzhi,Feng, Xiaofeng,Lei, Jian,Chen, Tieqiao,Zhou, Yongbo,Han, Li-Biao,Au, Chak-Tong,Yin, Shuang-Feng
-
supporting information
p. 4244 - 4247
(2014/07/21)
-
- Iridium(I)-catalyzed regioselective C-H activation and hydrogen-isotope exchange of non-aromatic unsaturated functionality
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Isotopic labelling is a key technology of increasing importance for the investigation of new C-H activation and functionalization techniques, as well as in the construction of labelled molecules for use within both organic synthesis and drug discovery. Herein, we report for the first time selective iridium-catalyzed C-H activation and hydrogen-isotope exchange at the β-position of unsaturated organic compounds. The use of our highly active [Ir(cod)(IMes)(PPh3)][PF6] (cod = 1, 5-cyclooctadiene) catalyst, under mild reaction conditions, allows the regioselective β-activation and labelling of a range of α, β-unsaturated compounds with differing steric and electronic properties. This new process delivers high levels of isotope incorporation over short reaction times by using low levels of catalyst loading.
- Kerr, William J.,Mudd, Richard J.,Paterson, Laura C.,Brown, Jack A.
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supporting information
p. 14604 - 14607
(2015/03/04)
-
- Copper-catalyzed synthesis of α,β-unsaturated acylamides via direct amidation from cinnamic acids and N-substituted formamides
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A highly effective synthesis of α,β-unsaturated acylamides is reported for the first time via copper-catalyzed direct amidation between readily available cinnamic acids and N-substituted formamides. The protocol was easily accessible and practical.
- Yan, Hong,Yang, Hailong,Lu, Linhua,Liu, Defu,Rong, Guangwei,Mao, Jincheng
-
supporting information
p. 7258 - 7263
(2013/08/23)
-
- Copper-catalyzed oxidative coupling of carboxylic acids with formamides for the synthesis of α,β-unsaturated amides
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A novel and efficient protocol for the synthesis of α,β- unsaturated amides has been developed using catalytic amount of Cu(OAc) 2 and TBHP as an available oxidant. Oxidative coupling of various unsaturated carboxylic acids with N,N-disubstituted formamides was examined to furnish the desired products in good yields.
- Li, Huamin,Pan, Changduo,Cheng, Yixiang,Zhu, Chengjian
-
supporting information
p. 6679 - 6681
(2013/11/19)
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- A novel one-step synthesis of benzo[b]furo[3,2-b]pyridines having an amino group at the 4-position from benzo[b]furo[3,2-d][1,3]oxazine
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A novel one-step synthesis of benzo[b]furo[3,2-b]pyridines having an amino group at the 4-position from benzo[b]furo[3,2-d][1,3]oxazine by treatment of various amines is described.
- Tabuchi, Yukako,Kakumoto, Yusa,Uchimoto, Hitomi,Kawasaki, Ikuo,Ohishi, Yoshitaka,Nishide, Kiyoharu
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p. 177 - 191
(2013/03/13)
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- N-palmitoylethanolamide derivatives: Synthesis and studies on anticonvulsant and antidepressant activities
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A series novel of N-palmitoylethanolamide derivatives was synthesized and screened for their anticonvulsant and antidepressant activities. Anticonvulsant activities and neurotoxicities of compounds when injected intraperitoneally (i.p.) were determined by maximal electroshock seizure (MES) test and a rotarod test, respectively, in mice. Only four of the synthesized compounds (3a, 3b, 3c, and 3d) showed anticonvulsant activity at a dose of 100 mg/kg. Six compounds showed reduced immobility durations during the forced swimming test at a dose of 10 mg/kg, indicative of antidepressant activity. Among the compounds, N-(3-hydroxypropyl)cinnamamide (3a) was the most promising compound and significantly reduced the duration of immobility duration by 23.36% at a dose of 10 mg/kg compared with the control (P0.01). Springer Science+Business Media, LLC 2010.
- Guan, Li-Ping,Sui, Xin,Deng, Xian-Qing,Zhao, Dong-Hai,Qu, You-Le,Quan, Zhe-Shan
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experimental part
p. 601 - 606
(2012/04/10)
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- RhIII-catalyzed oxidative olefination of vinylic C-H bonds: Efficient and selective access to Di-unsaturated α-amino acid derivatives and other linear 1,3-butadienes
-
Olefin(s) get-together! A RhIII-catalyzed oxidative cross-coupling of different olefins was developed, resulting in the formation of valuable linear butadiene products and especially di-unsaturated α-amino acid derivatives. 1,1-Di-, 1,2-di-, and 1,1,2-trisubstituted olefins could be coupled with styrenes and acrylates. In these reactions, remarkably high levels of chemo-, regio-, and stereoselectivity were obtained, rendering this a valuable synthetic tool. Copyright
- Besset, Tatiana,Kuhl, Nadine,Patureau, Frederic W.,Glorius, Frank
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supporting information; experimental part
p. 7167 - 7171
(2011/07/31)
-
- Copper-catalyzed bis(methoxycarbonyl)carbene reactions of α,β-unsaturated carboxamides
-
The [Cu(acac)2]-catalyzed reactions of α,β- unsaturated carboxamides with dimethyl diazomalonate yielded dihydrofuran derivatives by a 1,5-electrocyclic reaction at C(β), and butadiene derivatives by carbene addition reaction at C(α) (Schemesa
- Merey, Goekce,Anac, Olcay
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experimental part
p. 1053 - 1064
(2011/08/05)
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- Total regioselective transformation of aromatic aziridine 2-carboxamides into 2-aminoamides promoted by active manganese
-
(Figure Presented) A novel, totally regioselective transformation of aromatic N-4-methoxyphenylaziridine 2-carboxamides into 2-aminoamides promoted by active manganese (Mn) is reported. a-Amino ketones can be readily obtained by reaction of morpholine-der
- Concellon, Jose M.,Rodriguez-Solla, Humberto,Del Amo, Vicente,Diaz, Pamela
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experimental part
p. 2407 - 2410
(2010/06/21)
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- Indium-mediated microwave-assisted one-pot synthesis of α,β-unsaturated amides
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A stereoselective synthesis of α,β-unsaturated-N,N-diethyl amides was achieved by a one-pot reaction of triphenylphosphine, an aromatic aldehyde, and N,N-diethyl chloroacetamide in the presence of indium under microwave-assisted and solvent-free condition.
- Feng, Sunlin,Jiang, Shilei,Zhang, Zhiying,Yu, Xiaochun
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experimental part
p. 392 - 394
(2010/11/18)
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- Synthesis of α β,-unsaturated amide via phosphonium ylide
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A series of ,-unsaturated amides were prepared by the Wittig reaction of N,N-diethylamidemethylenetriphenylphosphorane ylide with aldehydes with moderate to good yields. Copyright Taylor & Francis Group, LLC.
- Jiang, Shilei,Yang, Kefeng,Yu, Xiaochun
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supporting information; experimental part
p. 1759 - 1767
(2009/11/30)
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- Microwave-assisted one-pot synthesis of α, β-unsaturated amides under solvent-free conditions
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Under microwave-assisted solvent-free conditions a one-pot reaction of triphenylphosphine, an aldehyde and N, N-diethyl chloroacetamide in the presence of zinc dust affords α, β-unsaturated amides stereoselectively in good yield. In comparison with the co
- Jiang, Shilei,Xie, Yuanyuan,Yu, Xiaochun
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experimental part
p. 24 - 26
(2009/10/02)
-
- Stereoselective olefination reactions promoted by Rieke manganese
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A study of the advantages of using manganese, an inexpensive and nontoxic metal, to perform stereoselective β-elimination reactions and to promote sequential olefination reactions of aldehydes to obtain α,β- unsaturated esters and amides is presented. Various elimination reactions, all of them characterized by occurring with complete stereoselectivity and in high yields, were performed using active manganese (Mn*) as metalating agent. This ability of manganese has been applied to develop a novel and direct synthesis of (E)-α,β-unsaturated esters or amides and (Z)-α,β-unsaturated α-halo esters and α-choroamides through a Mn*-mediated sequential olefination protocol of aldehydes with dichloro esters or amides and trihalo esters or trichloroamides, respectively. Georg Thieme Verlag Stuttgart.
- Concellon, Jose M.,Rodriguez-Solla, Humberto,Del Amo, Vicente,Diaz, Pamela
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experimental part
p. 2634 - 2645
(2009/12/06)
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- Sequential reactions promoted by manganese: Completely stereoselective synthesis of (E)-α,β-unsaturated amides, ketones, aldehydes, and carboxylic acids
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(Chemical Equation Presented) A complete E-selective synthesis of α,β-unsaturated amides through a sequential reaction of a range of dichloroamides with a variety of aldehydes promoted by Rieke manganese (Mn*) is reported. A mechanism based on a sequential aldol-type reaction and a completely stereoselective β-elimination is proposed to explain these results. The unsaturated amides obtained are readily and efficiently transformed into α,β-unsaturated ketones, aldehydes, or carboxylic acids without loss of the diastereoisomeric purity of the C-C double bond.
- Concellon, Jose M.,Rodriguez-Solla, Humberto,Diaz, Pamela
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p. 7974 - 7979
(2008/02/13)
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- Stereospecific cyclopropanation of highly substituted C-C double bonds promoted by CrCl2. Stereoselective synthesis of cyclopropanecarboxamides and cyclopropyl ketones
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We describe herein a CrCl2-promoted cyclopropanation of α,β-unsaturated amides. This reaction can be carried out on (E)- or (2)-α,β-enamides in which the C-C double bond is di-, tri-, or tetrasubstituted. In all cases the process is completely stereospecific and only a single diastereoisomer is obtained. In addition, cyclopropyl ketones were readily prepared by reaction of the cyclopropanecarboxamides (derived from morpholine) obtained with a range of organolithium compounds. A mechanism has been proposed to explain the cyclopropanation reaction.
- Concellon, Jose M.,Rodriguez-Solla, Humberto,Mejica, Carmen,Blanco, Elena G.
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p. 2981 - 2984
(2008/02/09)
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- Phenylsilane as an active amidation reagent for the preparation of carboxamides and peptides
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The use of phenylsilane as a mild coupling reagent for amidation reactions is reported. Applicability to both solution- and solid-phase chemistry has been demonstrated for a variety of amines and carboxylic acids.
- Ruan, Zheming,Lawrence, R. Michael,Cooper, Christopher B.
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p. 7649 - 7651
(2007/10/03)
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- METHOD FOR PRODUCTION OF Γ(A),Γ(B)-UNSATURATED AMIDE COMPOUNDS
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The invention relates to a method for production of α,β-unsaturated amide compounds of general formula (I): whereby (A) a protective group is introduced into a molecule of general formula (II) to give a compound of formula (III), (B) the compound obtained is reacted in the presence of (i) a dehydrogenation catalyst and (ii) a suitable oxidation agent and (C) the protective groups are removed.
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Page/Page column 15; 8
(2010/02/10)
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- Superacidic activation of α,β-unsaturated amides and their electrophilic reactions
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The electrophilic reactivity of α,β-unsaturated amides towards weak nucleophiles such as arenes and cyclohexane, initiated either with triflic acid (CF3SO3H) or with excess AlCl3, has been studied. The amides generally condense readily with aromatics in the presence of AlCl3 to give 3-arylpropionamides and related compounds in excellent yields, while some amides also undergo selective ionic hydrogenation with cyclohexane to give saturated amides. The proposed mechanism of these reactions involves dicationic intermediates (superelectrophiles). The direct observation of a dicationic species (by low-temperature NMR) is reported. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Koltunov, Konstantin Yu.,Walspurger, Stephane,Sommer, Jean
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p. 4039 - 4047
(2007/10/03)
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- Superelectrophilic activation of polyfunctional organic compounds using zeolites and other solid acids
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Zeolites and other available solid acids have been successfully applied to initiate reactions, which were earlier recognised to involve superelectrophilic intermediates and thus required excess of superacids to be carried out.
- Koltunov, Konstantin Yu.,Walspurger, Stéphane,Sommer, Jean
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p. 1754 - 1755
(2007/10/03)
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- Esters, amides and substituted derivatives of cinnamic acid: Synthesis, antimicrobial activity and QSAR investigations
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A series of esters (Ia-k), substituted derivatives (II a-d) and amides (IIIa-q) of cinnamic acid were synthesized and evaluated as antibacterial and antifungal agents. All the derivatives belonging to the series I, II and III showed antimicrobial activity comparable to the standard. Compounds If and IIc proved to be the most effective compounds. Quantitative structure-activity relationship (QSAR) investigation with multiple linear regression analysis was applied to find a correlation between different calculated physicochemical parameters of the compounds and biological activity. The quantitative models relating the structural features of cinnamic acid derivatives Ia-k, II a-d and IIIa-q and their antimicrobial activity showed that Gram negative Escherichia coli and Candida albicans (fungus) were the most sensitive microorganisms.
- Narasimhan, Balasubramanian,Belsare, Deepak,Pharande, Devayani,Mourya, Vishnukant,Dhake, Avinash
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p. 827 - 834
(2007/10/03)
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- Sequenced elimination-reduction and elimination-cyclopropanation reactions of 2,3-epoxyamides promoted by samarium diiodide. Synthesis of 2,3-dideuterioamides and cyclopropanamides
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An easy and general sequenced elimination/reduction or elimination/ cyclopropanation process promoted by samarium diiodide or/and CH 2I2/Sm provide an efficient method for synthesising 2,3-dideuterioamides 3 or cyclopropanamides 8, respectively. The transformations take place in high yields and with total or high selectivity from the easily available 2,3-epoxyamides. Graphical Abstract
- Concellón, José M.,Huerta, Mónica,Bardales, Eva
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p. 10059 - 10065
(2007/10/03)
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- Synthesis of Aromatic (E)- or (Z)-α,β-Unsaturated Amides with Total or Very High Selectivity from α,β-Epoxyamides and Samarium Diiodide
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Highly stereoselective synthesis of aromatic α,β-unsaturated amides was achieved by treatment of aromatic α,β-epoxyamides with samarium diiodide. The starting compounds 1 and 3 are easily prepared by the reaction of enolates derived from α-chloroamides wi
- Concellon, Jose M.,Bardales, Eva
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p. 9492 - 9495
(2007/10/03)
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- Synthesis of (E)-α,β-unsaturated amides with high selectivity by using samarium diiodide
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Stereoselective β-elimination of 2-chloro-3-hydroxyamides 1 is achieved by using samarium diiodide to yield α,β-unsaturated amides 2, in which the C=C bond is di- tri-, or tetrasubstituted. The starting compounds 1 are easily prepared by reaction of the c
- Concellon, Jose M.,Perez-Andres, Juan A.,Rodriguez-Solla, Humberto
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p. 3062 - 3068
(2007/10/03)
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