- Synthesis of Some New Acetanilide Derivatives as COX Inhibitors and Assessment of Analgesic/Anti-Inflammatory Activities
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The purpose of the present research was to synthesize a new series of acetanilide derivatives that would have analgesic and anti-inflammatory properties in laboratory animals (rats). IR spectroscopy, 1HNMR spectroscopy and Mass spectroscopy wer
- Kumar, Arvind,Mishra, Arun K.,Singh, Rajib Kumar
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p. 1475 - 1487
(2022/01/24)
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- An Environmentally Benign, Catalyst-Free N?C Bond Cleavage/Formation of Primary, Secondary, and Tertiary Unactivated Amides
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Herein, we report an operationally simple, cheap, and catalyst-free method for the transamidation of a diverse range of unactivated amides furnishing the desired products in excellent yields. This protocol is environmentally friendly and operates under extremely mild conditions without using any promoter or additives. Significantly, this strategy has been implied in the chemoselective synthesis of a pharmaceutical molecule, paracetamol, on a gram-scale with excellent yield. We anticipate that this universally applicable strategy will be of great interest in drug discovery, biochemistry, and organic synthesis.
- Kumar, Vishal,Dhawan, Sanjeev,Girase, Pankaj Sanjay,Singh, Parvesh,Karpoormath, Rajshekhar
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p. 5627 - 5639
(2021/11/11)
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- Copper-catalyzed transformation of alkyl nitriles to N -arylacetamide using diaryliodonium salts
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This work reports a simple and efficient method for the copper-catalyzed redox-neutral transformation of alkyl nitriles using eco-friendly diaryliodonium salts and leading to N-arylacetamides. The method features high efficiency, broad substrate scope and good functional group tolerance.
- Sallio, Romain,Payard, Pierre-Adrien,Pakulski, Pawe?,Diachenko, Iryna,Fabre, Indira,Berteina-Raboin, Sabine,Colas, Cyril,Ciofini, Ilaria,Grimaud, Laurence,Gillaizeau, Isabelle
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p. 15885 - 15889
(2021/05/19)
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- Sulfuryl Fluoride Mediated Synthesis of Amides and Amidines from Ketoximes via Beckmann Rearrangement
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A metal-free and redox-neutral method for Beckmann rearrangement employing inexpensive and readily available SO2F2 gas is described. The reported transformation proceeds at ambient temperature and is compatible with a wide range of sterically and electronically diverse aromatic, heteroaromatic, aliphatic and lignin-like oximes providing amides in good to excellent yields. The reaction proceeds through the formation of an imidoyl fluoride intermediate that can also be used for the synthesis of amidines.
- Gurjar, Jitendra,Fokin, Valery V.
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p. 10402 - 10405
(2020/07/25)
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- Solvent-free iron(III) chloride-catalyzed direct amidation of esters
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Amide functional groups are prominent in a broad range of organic compounds with diverse beneficial applications. In this work, we report the synthesis of these functional groups via an iron(iii) chloride-catalyzed direct amidation of esters. The reactions are conducted under solvent-free conditions and found to be compatible with a range of amine and ester substrates generating the desired amides in short reaction times and good to excellent yields at a catalyst loading of 15 mol%.
- Mkhonazi, Blessing D.,Shandu, Malibongwe,Tshinavhe, Ronewa,Simelane, Sandile B.,Moshapo, Paseka T.
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supporting information
(2020/03/17)
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- Transformation of lignin model compounds to: N -substituted aromatics via Beckmann rearrangement
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Here we present the highly effective cleavage of C-C bonds in lignin model compounds for the production of N-substituted aromatics in up to 96% total yield, including benzonitriles and amides, via oxime formation followed by Beckmann rearrangement (BR). The amides could be further hydrolyzed to anilines (>92% yield) and carboxylic acids (>90% yield), respectively. In addition, the employment of a substrate with a γ-OH group will lead to the formation of C-2 monosubstituted oxazole. A one-pot process involving the BR reaction and hydrolysis has also been developed to directly afford an up to 96% total yield of benzonitriles, benzamides, and anilines. This strategy enabled us to successfully apply the BR reaction to the degradation of lignin model compounds to N-functionalized aromatic products under mild conditions.
- Wang, Yinling,Du, Yiman,He, Jianghua,Zhang, Yuetao
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supporting information
p. 3318 - 3326
(2018/07/29)
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- The catalytic activity of titania nanostructures in the synthesis of amides under solvent-free conditions
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Different shapes and phases of titania nanostructures with the uniform size distribution were synthesized by hydrothermal sol-gel technique. The influence of annealing temperature on the crystalline character, size and phase of the prepared nanomaterials were evidenced from the diffraction analysis. Infrared spectroscopic analysis ensured the structural confirmation of the sulfated titania nanostructures. Catalytic activity of the synthesized nanometric materials in direct amidation of aromatic and aliphatic carboxylic acids with aromatic amines was evaluated. Among the materials studied, sulfated titania nanotubes with the anatase phase exhibited excellent catalytic activity. The employed solvent-free protocol is greener and eradicates the drawbacks associated with the hazardous solvents employed in the prevailing solution phase methodologies.
- Nagarajan, Sangaraiah,Ran, Park,Shanmugavelan, Poovan,Sathishkumar, Murugan,Ponnuswamy, Alagusundaram,Suk Nahm, Kee,Gnana Kumar
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p. 1312 - 1319
(2012/10/29)
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- Mild, powerful, and robust methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively
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We developed two efficient practical methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively. The present mild and robust reaction was performed by two separate methods both by combining cheap and readily available amines, N-methylimidazole, and N,N,N′,N′-tetramethylethylenediamine (TMEDA). Method A uses catalytic N-methylimidazole and TMEDA with an equimolar amount of K2CO3, whereas Method B uses equimolar amounts of N-methylimidazole and TMEDA. The salient features are as follows. (i) With regard to reactivity, Method B was superior to Method A for esterification and thioesterification, whereas cost-effective Method A was superior to Method B for amide formation. (ii) Amide formation proceeded smoothly between acid chlorides and less nucleophilic and stereocongested amines such as 2,6-dichloroaniline. (iii) This protocol was applied to the successful synthesis of two agrochemicals, bromobutide and carpropamid.
- Nakatsuji, Hidefumi,Morimoto, Mami,Misaki, Tomonori,Tanabe, Yoo
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p. 12071 - 12080
(2008/03/13)
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- Facile stereoselective synthesis of 1,3-disubstituted-4-trichloromethyl azetidin-2-ones
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The highly stereoselective synthesis of 1,3-disubstituted-4-trichloromethyl azetidin-2-ones by the [2+2] cycloaddition of ketenes with imines derived from chloral is described. The highly stereoselective synthesis of 1,3-disubstituted-4-trichloromethyl azetidin-2-ones by the [2+2] cycloaddition of ketenes with imines derived from chloral is described.
- Govande,Deshmukh
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p. 6563 - 6566
(2007/10/03)
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- A convenient preparation of N-alkyl and N-arylamines by smiles rearrangement - Synthesis of analogues of diclofenac
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Smiles rearrangement of substituted aryloxyacetamides in which oxygen and nitrogen are separated by COCH2 group has been successful even when the aryloxy ring carries weak or no electron withdrawing group. Earlier reports of such reactions involved either strong electron withdrawing groups or a special catalyst. The diphenylamines thus obtained gave analogues of diclofenac in only one case.
- Wadia,Patil
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p. 2725 - 2736
(2007/10/03)
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- Efficient procedure for the preparation of amides using polymer-bound reagents
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An effective method for the conversion of acids into amides is presented. The two-step procedure includes the preparation of acid chloride intermediates using Pol-Ph3P and subsequent treatment of these intermediates with amines and polymer-bound base. The amides were accessible in high yields and purities without further purification.
- Buchstaller,Ebert,Anlauf
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p. 1001 - 1005
(2007/10/03)
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- Selective Activation of Primary Carboxylic Acids by Electron-rich Triarylbismuthanes. Application to Amide and Ester Synthesis under Neutral Conditions
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On being heated in benzene in the presence of tris(methoxyphenyl)bismuthanes 1b-1e, primary carboxylic acids are selectively activated to couple with amines and alcohols to produce the corresponding amides and esters in satisfactory yields, while secondary, tertiary and aromatic carboxylic acids remain unaffected. 2-Benzylmalonic acid is similarly converted into its corresponding diamides and diesters, but 2,2-dibenzylmalonic acid suffers extensive decarboxylation and, in the presence of aromatic olefins, it undergoes a novel -type cycloaddition reaction to form 4-substituted 2,2-dibenzyl-4-butanolides in low to fair yields.
- Ogawa, Takuji,Hikasa, Tetsuya,Ikegami, Tohru,Ono, Noboru,Suzuki, Hitomi
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p. 3473 - 3478
(2007/10/02)
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- Electron-rich Triarylbismuthines as Selective Condensation Reagent under Neutral Conditions. Condensation of Aliphatic Carboxylic Acids with Amines and Alcohols
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On heating with amines or alcohols in the presence of tris(2-methoxyphenyl)- or tris(2,6-dimethoxyphenyl)bismuthine, carboxylic acids bearing α-hydrogen are readily converted into the corresponding amides or esters in good yields while those without α-hydrogen remain intact.
- Ogawa, Takuji,Hikasa, Tetsuya,Ikegami, Tohru,Ono, Noboru,Suzuki, Hitomi
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p. 815 - 818
(2007/10/02)
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- Water-Soluble Acylating Agents: Preparation of 2-Acylthio-1-alkylpyridinium Salts and Acylation of Phenols, Acids, and/or Amines with These Salts in an Aqueous Phase
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Reaction of phenols, amines, and acids with 2-benzoylthio-1-methylpyridinium chloride prepared in situ from benzoyl chloride and 1-methyl-2(1H)-pyridinethione, afforded the corresponding benzoyl derivatives in good yields.In the reaction of p-nitrophenol, even catalytic amount of 1-methyl-2(1H)-pyridinethione proved to be effective.Similar reactions of p-nitrophenol with isobutyryl chloride and acetyl chloride in the presence of 1-methyl-2(1H)-pyridinethione afforded p-nitrophenyl isobutyrate and p-nitrophenyl acetate in 63 and 44percent yields, respectively. 2-Benzoylthio-, 2-acetylthio-, and 2-isobutyrylthio-1-ethylpyridinium tetrafluorobora tes were prepared by treatment of the corresponding 2-acylthiopyridines with triethyloxonium tetrafluoroborate.These pyridinium salts also acted as acylating agents in an aqueous phase. some competitive reactions of 2-aminoethanol and phenols with 2-benzoylthio-1-methylpyridinium chloride were also investigated.
- Sakakibara, Tohru,Watabe, Yukie,Yamada, Masahide,Sudoh, Rokuro
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p. 247 - 254
(2007/10/02)
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- Preparation of Alkyl Chlorides, Acid Chlorides, and Amides Using Polymer-Supported Phosphines and Carbon Tetrachloride: Mechanism of These Reactions
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Alcohols and thiols were converted into alkyl chlorides, carboxylic acids were converted into acid chlorides, and mixtures of carboxylic acids and amines were converted into amides by reaction with carbon tetrachloride and 1percent cross-linked polystyrenes containing phosphine residues.Some of these conversions were also effected by using a linear polymer containing phosphine residues.The reactions proceed in high yield, and isolation of the products is facilitated by the ready removal of all the polymer-supported species.The mechanism of the reactions between triphenylphosphine, carbon tetrachloride, and alcohols is complex, but the polymer-supported reactions appear to follow analogous pathways to the low molecular weight reactions as judged by the yields of chloroform and the number of equivalents of phosphine consumed per mole of alkyl chloride produced.The mechanism requires polymer-supported groups reacting together.The slow step in the reactions appears to be the generation of the chlorinating species.The polymer-supported reactions are faster than those using triphenylphosphine or 4-(diphenylphosphinyl)isopropylbenzene.It is suggested that this is due to a microenvironmental effect.
- Harrison, Charles R.,Hodge, Philip,Hunt, Barry J.,Khoshdel, Ezzatollah,Richardson, Graham
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p. 3721 - 3728
(2007/10/02)
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- Quantitative structure activity relationship of reversible dihydrofolate reductase inhibitors. Diaminotriazines
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A quantitative structure activity relationship (QSAR) has been formulated for 4,6 diamino 1,2 dihydro 2,2 dimethyl 1 (X phenyl) s triazines inhibiting dihydrofolate reductase, isolated from Walker 256 tumor. Using substituent constants and regression analysis, it is shown that the substituents X on the phenyl ring are placed into two different types of space in, or on, the enzyme. Substituents in the 3 position show typical hydrophobic interaction while substituents in the 4 position bring about inhibition in a fashion more closely related to their molecular volume as characterized by molecular refractivity. The electronic effects of X as measured by sigma do not appear to have a significant role. The QSAR for 83 inhibitors is described by log 1/C = 0.89(π-3) + 0.15(MR-4) - 0.13(π-3)2 + 6.62, where π-3 is the hydrophobic effect of substituents in the 3 position, and MR-4 is the molecular refractivity of 4 substituents. The correlation coefficient for this equation is 0.905. The design of better inhibitors is discussed in the light of the above equation.
- Hansch,Silipo
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p. 661 - 667
(2007/10/05)
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