- Ruthenium-catalyzed cyclization of aromatic nitriles with alkenes: Stereoselective synthesis of (Z)-3-methyleneisoindolin-1-ones
-
Aromatic nitriles underwent cyclization with activated alkenes in the presence of a ruthenium catalyst, AgSbF6, and Cu(OAc)2·H2O providing substituted 3-methyleneisoindolin-1-ones with high Z-stereoselectivity. The Z-stereoselectivity of the 3-methyleneisoindolin-1-one moiety was controlled by the intramolecular hydrogen bonding.
- Reddy, Mallu Chenna,Jeganmohan, Masilamani
-
-
Read Online
- Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups
-
We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.
- Govindan, Karthick,Chen, Nian-Qi,Chuang, Yu-Wei,Lin, Wei-Yu
-
supporting information
p. 9419 - 9424
(2021/11/30)
-
- Ring Opening/Site Selective Cleavage in N-Acyl Glutarimide to Synthesize Primary Amides
-
A LiOH-promoted hydrolysis selective C-N cleavage of twisted N-acyl glutarimide for the synthesis of primary amides under mild conditions has been developed. The reaction is triggered by a ring opening of glutarimide followed by C-N cleavage to afford primary amides using 2 equiv of LiOH as the base at room temperature. The efficacy of the reactions was considered and administrated for various aryl and alkyl substituents in good yield with high selectivity. Moreover, gram-scale synthesis of primary amides using a continuous flow method was achieved. It is noted that our new methodology can apply under both batch and flow conditions for synthetic and industrial applications.
- Govindan, Karthick,Lin, Wei-Yu
-
supporting information
p. 1600 - 1605
(2021/03/03)
-
- Amine-Mediated Bond Cleavage in Oxidized Lignin Models
-
Introducing amines/ammonia into lignin cracking will allow novel bond cleavage pathways. Herein, a method of amines/ammonia-mediated bond cleavage in oxidized lignin β-O-4 models was studied using a copper catalyst at room temperature, demonstrating the effect of the amine source on the selectivity of products. For primary and secondary aliphatic amines, lignin ketone models underwent oxidative Cα?Cβ bond cleavage and Cα?N bond formation to generate aromatic amides. For ammonia, the competition between oxygen and ammonia determined the selectivity between Cα?N and Cβ?N bond formation, generating amides and α-keto amides, respectively. For tertiary amines, the lignin models underwent oxidative Cα?Cβ bond cleavage to benzoic acids. Control experiments indicated that amines act as nucleophiles attacking at the Cα or Cβ position of the oxidized β-O-4 linkage to be cleaved. This study represents a novel example that the breakage of oxidized lignin model can be regulated by amines with a copper catalyst.
- Li, Hongji,Liu, Meijiang,Liu, Huifang,Luo, Nengchao,Zhang, Chaofeng,Wang, Feng
-
p. 4660 - 4665
(2020/07/04)
-
- Transamidation for the Synthesis of Primary Amides at Room Temperature
-
Various primary amides have been synthesized using the transamidation of various tertiary amides under metal-free and mild reaction conditions. When (NH4)2CO3 reacts with a tertiary amide bearing an N-electron-withdrawing substituent, such as sulfonyl and diacyl, in DMSO at 25 °C, the desired primary amide product is formed in good yield with good funcctional group tolerance. In addition, N-tosylated lactam derivatives afforded their corresponding N-tosylamido alkyl amide products via a ring opening reaction.
- Chen, Jiajia,Lee, Sunwoo,Xia, Yuanzhi
-
supporting information
(2020/05/05)
-
- Ruthenium(III) 2-(aminofluoreneazo)phenolate complexes: Synthesis, characterization, catalytic activity in amidation reaction and Fluorescence quenching studies
-
A series of ruthenium(III)2-(aminofluoreneazo)phenolate complexes with general formula [RuCl(PPh3)2(L1-5)] (1–5) (L = 2-(aminofluoreneazo)phenolate ligands) have been synthesized. The characterization of the synthesized complexes was accomplished by elemental analysis, spectroscopic (FT-IR, UV–Vis, Fluorescence and EPR) and ESI-MStechniques. The catalytic performance of one of the synthesized complexes 3 for the amidation of aldehyde in the presence of NaHCO3/NH2OH·HCl has been evaluated. The fluorescence emission of complexes [RuCl(PPh3)2(L2)] (2) and [RuCl(PPh3)2(L3) (3)] are effectively quenched by 1,4-benzoquinone and 1,4-naphthoquinone in acetonitrile medium.
- Thirumal, Muniyappan,Venkatachalam, Galmari,Venkattappan, Anbazhagan
-
-
- Base promoted peroxide systems for the efficient synthesis of nitroarenes and benzamides
-
A useful and efficient approach for the synthesis of nitroarenes from several aromatic amines (including heterocycles) using peroxide and base has been developed. This oxidative reaction is very easy to handle and afforded the products in good yields. Formation of benzamides from benzylamine was also successfully carried out with this metal-free catalytic system in good to excellent yields.
- Gupta, Sampa,Ansari, Alisha,Sashidhara, Koneni V.
-
supporting information
(2019/09/07)
-
- Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides to Form Nitriles
-
A palladium(II) catalyst, in the presence of Selectfluor, enables the efficient and chemoselective transformation of primary amides into nitriles. The amides can be attached to aromatic rings, heteroaromatic rings, or aliphatic side chains, and the reactions tolerate steric bulk and electronic modification. Dehydration of a peptaibol containing three glutamine groups afforded structure-activity relationships for each glutamine residue. Thus, this dehydration can act similarly to an alanine scan for glutamines via synthetic mutation.
- Al-Huniti, Mohammed H.,Rivera-Chávez, José,Colón, Katsuya L.,Stanley, Jarrod L.,Burdette, Joanna E.,Pearce, Cedric J.,Oberlies, Nicholas H.,Croatt, Mitchell P.
-
supporting information
p. 6046 - 6050
(2018/09/27)
-
- Transformation of lignin model compounds to: N -substituted aromatics via Beckmann rearrangement
-
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
-
supporting information
p. 3318 - 3326
(2018/07/29)
-
- Highly Selective Ruthenium-Catalyzed Direct Oxygenation of Amines to Amides
-
Reports on aerobic oxidation of amines to amides are rare, and those reported suffer from several limitations like poor yield or selectivity and make use of pure oxygen under elevated pressure. Herein, we report a practical and an efficient ruthenium-catalyzed synthetic protocol that enables selective oxidation of a broad range of primary aliphatic, heterocyclic and benzylic amines to their corresponding amides, using readily available reagents and ambient air as the sole oxidant. Secondary amines instead, yield benzamides selectively as the sole product. Mechanistic investigations reveal intermediacy of nitriles, which undergo hydration to afford amide as the final product.
- Ray, Ritwika,Hazari, Arijit Singha,Chandra, Shubhadeep,Maiti, Debabrata,Lahiri, Goutam Kumar
-
supporting information
p. 1067 - 1071
(2018/01/03)
-
- Metal-Free Thermal Activation of Molecular Oxygen Enabled Direct α-CH2-Oxygenation of Free Amines
-
Direct oxidation of α-CH2 group of free amines is hard to achieve due to the higher reactivity of amine moiety. Therefore, oxidation of amines involves the use of sophisticated metallic reagents/catalyst in the presence or absence of hazardous oxidants under sensitive reaction conditions. A novel method for direct C-H oxygenation of aliphatic amines through a metal-free activation of molecular oxygen has been developed. Both activated and unactivated free amines were oxygenated efficiently to provide a wide variety of amides (primary, secondary) and lactams under operationally simple conditions without the aid of metallic reagents and toxic oxidants. The method has been applied to the synthesis of highly functionalized amide-containing medicinal drugs, such as O-Me-alibendol and -buclosamide.
- Ghosh, Santanu,Jana, Chandan K.
-
p. 260 - 266
(2018/02/19)
-
- Compounding method for hellebore amide
-
The invention provides a compounding method for hellebore amide. An ultraviolet spectrum technique and a mass-spectrometric technique are used for representing the structure of hellebore amide. The hellebore amide is prepared according to the following steps: performing nucleophilic addition on veratraldehyde and hydroxylamine hydrochloride and then performing beckmann rearrangement under the catalytic effect of cation exchange resin. The compounding method for hellebore amide has the advantages of simple compound process, high yield, reusable catalyst and benefit to realization of industrial production.
- -
-
Paragraph 0017
(2017/07/19)
-
- I2-Catalyzed Oxidative Amidation of Benzylamines and Benzyl Cyanides under Mild Conditions
-
We report a novel and efficient method for the oxidation of benzylic carbons (amines and cyanides) into corresponding benzamides using a catalytic amount of I2 and TBHP as the green oxidant via the C-H bond cleavage of the benzylic carbon under mild reaction conditions. According to the literature survey, this is the first report for the oxidative amidation of benzylamines and decyanation of benzyl cyanides in one pot under metal-free conditions.
- Nageswara Rao, Sadu,Reddy, N. Naresh Kumar,Samanta, Supravat,Adimurthy, Subbarayappa
-
p. 13632 - 13642
(2017/12/26)
-
- A method of from [...] amide
-
The invention discloses a method for synthesizing amides from oxime. The method is characterized by adding oxime, water and a water-soluble iridium complex catalyst to a reaction vessel, cooling a reactant to the room temperature after the reaction mixture reacts at 80-120 DEG C for several hours, removing water through selective evaporation, and obtaining a target product through column separation. Compared with existing methods for synthesizing amides through oxime rearrangement in water through transition metal catalysis, the method has the advantages that the used catalyst is low in load and does not contain phosphine ligands severely polluting the environment, so that the reaction can be carried out in the air, without nitrogen protection; therefore the reaction meets the green chemical requirements and has an extensive development prospect.
- -
-
Paragraph 0042-0046
(2017/01/31)
-
- A method from the aldehyde amide
-
The invention discloses a method for synthesizing amides from aldehyde. The method comprises the following steps: adding aldehyde, hydroxylamine hydrochloride, alkali and water to a reaction vessel to react at room temperature for half an hour; adding a water-soluble iridium complex after aldehyde is completely transformed into oxime, cooling a reactant to the room temperature after the reaction mixture reacts at 80-120 DEG C for several hours, removing water through selective evaporation, and obtaining a target product through column separation. Compared with existing methods for synthesizing amides by generating oxime through one-pot reaction between aldehyde and hydroxylamine in water and then carrying out rearrangement, the method has the advantages that the used catalyst is low in load and does not contain phosphine ligands severely polluting the environment, so that the reaction can be carried out in the air, without nitrogen protection; therefore the reaction meets the green chemical requirements and has an extensive development prospect.
- -
-
Paragraph 0047; 0048; 0049; 0050
(2017/04/08)
-
- Visible Light-Induced Iodine-Catalyzed Transformation of Terminal Alkynes to Primary Amides via C≡C Bond Cleavage under Aqueous Conditions
-
The visible light-induced iodine-catalyzed oxidative cleavage of the C≡C bond for transforming terminal alkynes into primary amides in the presence of ammonia under aqueous conditions is described. This metal-free protocol which ensued via initial hydroamination of the acetylene bond followed by liberation of diiodomethane (CH2I2) was found to be applicable to aromatic, heteroaromatic and aliphatic alkynes.
- Dighe, Shashikant U.,Batra, Sanjay
-
supporting information
p. 500 - 505
(2016/02/12)
-
- Aminofluorene-Mediated Biomimetic Domino Amination-Oxygenation of Aldehydes to Amides
-
A conceptually novel biomimetic strategy based on a domino amination-oxygenation reaction was developed for direct amidation of aldehydes under metal-free conditions employing molecular oxygen as the oxidant. 9-Aminofluorene derivatives acted as pyridoxamine-5′-phosphate equivalents for efficient, chemoselective, and operationally simple amine-transfer oxygenation reaction. Unprecedented RNH transfer involving secondary amine to produce secondary amides was achieved. In the presence of 18O2, 18O-amide was formed with excellent (95%) isotopic purity.
- Ghosh, Santanu,Jana, Chandan K.
-
supporting information
p. 5788 - 5791
(2016/11/29)
-
- Ferric perchlorate-mediated one-step reaction of [60]fullerene with primary amides for the synthesis of fullerooxazoles
-
The facile one-step reaction of [60]fullerene with primary amides promoted by cheap and easily available ferric perchlorate afforded a series of interesting fullerooxazole derivatives. The reaction was tolerant of a large variety of primary amides containing aryl, alkyl, and cinnamyl groups. A possible reaction mechanism for product formation was proposed.
- Zhang, Xiao-Feng,Li, Fa-Bao,Shi, Ji-Long,Wu, Jun,Liu, Li
-
p. 1626 - 1632
(2016/02/19)
-
- Oxidative Coupling between Methylarenes and Ammonia: A Direct Approach to Aromatic Primary Amides
-
A direct oxidative amidation between methylarenes and aqueous ammonia using a tert-butyl hydroperoxide and tetrabutylammonium iodide (TBHP/TBAI) oxidation system with co-catalysis of iron(III) chloride has been developed. Both coupling partners were used in their native form to render prior functionalization unnecessary and afford a facile approach to aromatic primary amides.
- Zhao, Zhenguang,Wang, Tao,Yuan, Lin,Hu, Xu,Xiong, Fei,Zhao, Junfeng
-
p. 2566 - 2570
(2015/08/18)
-
- One-Step Synthesis of Nitriles from Acids, Esters and Amides Using DIBAL-H and Ammonium Chloride
-
A convenient, one-step procedure is presented for the conversion of carboxylic acids or their derivatives (esters, lactones, amides) to nitriles with an aminoalane reagent prepared from diisobutylaluminum hydride (DIBAL-H) and ammonium chloride.
- Wojtkielewicz, Agnieszka,?otowski, Zenon,Morzycki, Jacek W.
-
supporting information
p. 2288 - 2292
(2015/09/28)
-
- Direct oxidative esterification of alcohols and hydration of nitriles catalyzed by a reusable silver nanoparticle grafted onto mesoporous polymelamine formaldehyde (AgNPs@mPMF)
-
A nitrogen-rich mesoporous organic polymer was synthesized as a novel support. A silver nanoparticle was synthesized and grafted onto it. The prepared catalyst (AgNPs@mPMF) was characterized by powder X-ray diffraction (XRD), scanning electron microscopy(SEM) and energy dispersive X-ray spectrometry (EDS), thermogravimetric analysis (TGA), high-resolution transmission electron microscopy (HRTEM), UV-vis diffuse reflectance spectroscopy (DRS), N2 adsorption, Raman spectroscopy and EPR study. The catalytic activity was evaluated for the oxidative esterification reaction of alcohols and hydration of nitriles. The oxidative esterification reaction was carried out for various activated alcohols giving excellent yields of the corresponding ester products. The catalyst was also efficient in the hydration of nitriles. Both reactions were optimized by varying the bases, temperatures and solvents. The catalyst can be facilely recovered and reused six times without a significant decrease in its activity and selectivity.
- Ghosh, Kajari,Iqubal, Md. Asif,Molla, Rostam Ali,Mishra, Ashutosh,Kamaluddin,Islam, Sk Manirul
-
p. 1606 - 1622
(2015/04/27)
-
- Synthesis of primary amides by aminocarbonylation of aryl/hetero halides using non-gaseous NH3 and CO sources
-
Abstract A practically simple method for the synthesis of primary amides via the palladium-catalysed aminocarbonylation of aromatic halides by using solid sources of gaseous ammonia and carbon monoxide is described. The system tolerated a wide variety of hindered and functionalized aryl/hetero halides and afforded good to excellent yields (69-94%) of the amide. Pharmacologically active Exalamide and Pyrazinecarboxamide were synthesised in high yields to demonstrate the effectiveness of this method.
- Suresh,Baburajan, Poongavanam,Ahmed, Mansur
-
supporting information
p. 4864 - 4867
(2015/07/28)
-
- Iodine-Mediated Domino Protocol for the Synthesis of Benzamides from Ethylarenes via sp3 C-H Functionalization
-
An efficient, metal-free domino protocol for the synthesis of benzamides has been developed from ethylarenes using aqueous ammonia. The reaction proceeds through the formation of triiodomethyl ketone intermediate in the presence of iodine as the promoter and TBHP as an oxidant followed by nucleophilic substitution with aqueous ammonia, forming an amide. This operationally simple, functional-group-tolerant tandem approach provides an easy access to the broad range of biologically important benzamides.
- Vadagaonkar, Kamlesh S.,Kalmode, Hanuman P.,Prakash, Sattey,Chaskar, Atul C.
-
supporting information
p. 1677 - 1682
(2015/07/20)
-
- Copper-catalyzed aerobic oxidative C-C bond cleavage for C-N bond formation: From ketones to amides
-
A novel copper-catalyzed aerobic oxidative C(CO)-C(alkyl) bond cleavage reaction of aryl alkyl ketones for C-N bond formation is described. A series of acetophenone derivatives as well as more challenging aryl ketones with long-chain alkyl substituents could be selectively cleaved and converted into the corresponding amides, which are frequently found in biologically active compounds and pharmaceuticals.
- Tang, Conghui,Jiao, Ning
-
supporting information
p. 6528 - 6532
(2014/06/24)
-
- Rearrangement of aldoximes to amides in water under air atmosphere catalyzed by water-soluble iridium complex [Cp*Ir(H2O) 3][OTf]2
-
In the presence of the water-soluble iridium complex [Cp*Ir(H 2O)3][OTf]2, a variety of aldoximes, including aromatic, aliphatic, conjugated unsaturated and non-conjugated unsaturated, were converted into their corresponding amides in water with good to excellent yields. Further, the one-pot synthesis of amides from aldehydes, hydroxylamine hydrochloride and sodium carbonate via a tandem condensation-rearrangement reaction in water was also accomplished. Compared with the reported organometallic catalysts for the rearrangement of aldoximes to amides in water, the present catalyst exhibited some advantages such as being phosphorus ligand-free, having low catalyst loading, and operational convenience under air atmosphere. This journal is the Partner Organisations 2014.
- Sun, Chunlou,Qu, Panpan,Li, Feng
-
p. 988 - 996
(2014/04/03)
-
- Molecular iodine-mediated domino reaction for the synthesis of benzamides, 2,2-Diazidobenzofuran-3(2H)-ones and benzoxazolones
-
A simple and efficient domino protocol has been developed for the preparation of biologically important benzamides, 2,2-diazidobenzofuran-3(2H)- ones and benzoxazolones from various structurally and electronically divergent acetophenones and ortho-hydroxyacetophenones in the presence of molecular iodine, sodium azide and sodium bicarbonate at 100 °C in good to excellent yields. Copyright
- Rajendar,Kant, Ruchir,Narender
-
supporting information
p. 3591 - 3596
(2014/01/06)
-
- Ruthenium-catalyzed aerobic oxidative cyclization of aromatic and heteroaromatic nitriles with alkynes: A new route to isoquinolones
-
The oxidative cyclization of aromatic and heteroaromatic nitriles with alkynes in the presence of a catalytic amount of [{RuCl2(p-cymene)} 2], Cu(OAc)2·H2O and KPF6 in acetic acid under air gave isoquinolones in good to excellent yields.
- Reddy, Mallu Chenna,Manikandan, Rajendran,Jeganmohan, Masilamani
-
supporting information
p. 6060 - 6062
(2013/07/19)
-
- Heterogeneous catalytic method for the conversion of aldoximes into nitriles using molecular sieve modified with Copper(II)
-
A simple heterogeneous metal-catalyzed method was developed for the transformation of aldoximes into nitriles. Molecular sieve (4 A) modified with copper(II) proved to be an efficient catalyst for the conversion. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
- Kiss, Arpad,Hell, Zoltan
-
supporting information
p. 1778 - 1786
(2013/05/22)
-
- A general and practical oxidation of alcohols to primary amides under metal-free conditions
-
A general procedure for oxidation of both benzyl alcohols and alkyl alcohols to primary amides under catalyst free conditions has been developed. 34 examples of primary amides were produced from their corresponding alcohols in moderate to excellent yields. This is a practical procedure for primary amides synthesis; water and tert-butanol are the only by-products. A commercial drug, Piracetam, was prepared in one step with 73% yield as well.
- Wu, Xiao-Feng,Sharif, Muhammad,Feng, Jian-Bo,Neumann, Helfried,Pews-Davtyan, Anahit,Langer, Peter,Beller, Matthias
-
p. 1956 - 1961
(2013/09/24)
-
- I2-TEMPO as an efficient oxidizing agent for the one-pot conversion of alcohol to amide using FeCl3 as the catalyst
-
A high yield one-pot method for the synthesis of amides from alcohols is described. The aldehyde was generated in situ using iodine-TEMPO as oxidizing agent followed by intermediate oxime formation through reaction with NH 2OH?HCl and finally rearrangement of oxime catalyzed by FeCl3.
- Das, Rima,Chakraborty, Debashis
-
experimental part
p. 48 - 53
(2012/08/28)
-
- Nitromethane in polyphosphoric acid- A new reagent for carboxyamidation and carboxylation of activated aromatic compou
-
A new method of carboxyamidation of aromatic compounds based on their reaction with nitromethane in polyphosphoric acid has been developed. Upon the hydrolysis of benzamides during the reaction mixture workup, the corresponding benzoic acids can be obtained. Taylor & Francis Group, LLC.
- Aksenov, Alexander V.,Aksenov, Nicolai A.,Nadein, Oleg N.,Aksenova, Inna V.
-
experimental part
p. 541 - 547
(2011/11/29)
-
- FeIII-catalyzed synthesis of primary amides from aldehydes
-
A direct synthetic route for the transformation of aldehydes into primary amides in the presence of catalytic amounts of FeCl3 in water is described. A direct synthetic route for the transformation of aldehydes into primary amides in the presence of catalytic amounts of FeCl3 in water is described. Copyright
- Gowda, Ravikumar R.,Chakraborty, Debashis
-
supporting information; experimental part
p. 2226 - 2229
(2011/06/17)
-
- One-pot synthesis of symmetrical 1,3-diarylureas or substituted benzamides directly from benzylic primary alcohols and effective oxidation of secondary alcohols to ketones using phenyliodine diacetate in combination with sodium azide
-
Benzylic primary alcohols can be directly converted into symmetrical 1,3-diarylureas or substituted benzamides via an one-pot oxidative reaction using the combined reagent of phenyliodine diacetate and sodium azide. This new reaction constitutes a step-economical way to prepare symmetric 1,3-diarylureas or substituted benzamides depending upon the substituents on the phenyl rings of starting alcohols. The sodium acetate generated in situ from the ligand exchange between phenyliodine diacetate and sodium azide plays the pivotal role in the formation of 1,3-diarylureas. In addition, it is also found that various secondary alcohols can be readily oxidized to their corresponding ketones in excellent yields using the same reagent system of phenyliodine diacetate and sodium azide. Generally, secondary alcohols are preferentially oxidized to the corresponding ketones in the presence of primary ones with the limited amounts of phenyliodine diacetate and sodium azide.
- Li, Xiao-Qiang,Wang, Wei-Kun,Han, Yi-Xin,Zhang, Chi
-
experimental part
p. 2588 - 2598
(2010/12/25)
-
- Palladium-catalyzed one-pot conversion of aldehydes to amides
-
The palladium-catalyzed one-pot conversion of aldehydes into primary amides in the presence of hydroxylamine hydrochloride in aqueous dimethyl sulfoxide (DMSO) at moderate temperature is described. The process is selective and free from the addition of an external chelating ligand.
- Ali, Md. Ashif,Punniyamurthy, Tharmalingam
-
experimental part
p. 288 - 292
(2010/04/28)
-
- Hansch analysis of veratric acid derivatives as antimicrobial agents
-
The synthesis, characterization and antimicrobial evaluation of a new series of veratric acid derivatives are presented. Preliminary in vitro antimicrobial activity of the title compounds was assessed against a panel of microorganisms including Gram-positive and Gram-negative bacteria and fungi. Some of the veratric acid derivatives exhibited significant in vitro antimicrobial activity. QSAR investigation applied to find a correlation between different physicochemical parameters of the veratric acid derivatives and their antimicrobial activity indicated the importance of topological parameters in describing the antimicrobial activity.
- Narasimhan, Balasubramanian,Ohlan, Sucheta,Ohlan, Ruchita,Judge, Vikramjeet,Narang, Rakesh
-
experimental part
p. 689 - 700
(2009/09/08)
-
- Discovery and biological evaluation of novel cyanoguanidine P2X7 antagonists with analgesic activity in a rat model of neuropathic pain
-
We disclose the design of a novel series of cyanoguanidines that are potent (IC50 ? 10-100 nM) and selective (≥100-fold) P2X7 receptor antagonists against the other P2 receptor subtypes such as the P2Y2, P2X4, and P2X3. We also found that these P2X7 antagonists effectively reduced nociception in a rat model of neuropathic pain (Chung model). Particularly, analogue 53 proved to be effective in the Chung model, with an ED50 of 38 μmol/kg after intraperitoneal administration. In addition compound 53 exhibited antiallodynic effects following oral administration and maintained its efficacy following repeated administration in the Chung model. These results suggest an important role of P2X7 receptors in neuropathic pain and therefore a potential use of P2X7 antagonists as novel therapeutic tools for the treatment of this type of pain.
- Perez-Medrano, Arturo,Donnelly-Roberts, Diana L.,Honore, Prisca,Hsieh, Gin C.,Namovic, Marian T.,Peddi, Sridhar,Shuai, Qi,Wang, Ying,Faltynek, Connie R.,Jarvis, Michael F.,Carroll, William A.
-
scheme or table
p. 3366 - 3376
(2010/04/03)
-
- Antibacterial alkoxybenzamide inhibitors of the essential bacterial cell division protein FtsZ
-
3-Methoxybenzamide is a weak inhibitor of the essential bacterial cell division protein FtsZ. Exploration of the structure-activity relationships of 3-methoxybenzamide analogues led to the identification of potent anti-staphylococcal compounds.
- Czaplewski, Lloyd G.,Collins, Ian,Boyd, E. Andrew,Brown, David,East, Stephen P.,Gardiner, Mihaly,Fletcher, Rowena,Haydon, David J.,Henstock, Vincent,Ingram, Peter,Jones, Clare,Noula, Caterina,Kennison, Leanne,Rockley, Chris,Rose, Valerie,Thomaides-Brears, Helena B.,Ure, Rebecca,Whittaker, Mark,Stokes, Neil R.
-
scheme or table
p. 524 - 527
(2011/02/28)
-
- A domino amidation route to indolines and indoles: Rapid syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine
-
(Chemical Equation Presented) When subjected to palladium-catalyzed amidation conditions, 2-triflyloxy phenethyl carbonates undergo, in addition to the expected aryl cross-coupling, an additional amidation with net displacement of the carbonate. The result is a one-step synthesis of indolines which may be oxidized to indoles. The utility of the procedure is illustrated by the two- or three-step syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine.
- Ganton, Michael D.,Kerr, Michael A.
-
p. 4777 - 4779
(2007/10/03)
-
- Reactions of Vilsmeier Haack reagent with aromatic and heterocyclic aldoximes
-
Reactions of Vilsmeier Haack reagent with various aromatic and heterocyclic aldoximes give amides. Nitriles are shown to be the intermediates in this reaction. Vilsmeier Haack reaction with amides in turn furnishes nitriles.
- Kusurkar, Radhika,Goswami, Shailesh,Vyas, Sandhya
-
p. 3148 - 3151
(2007/10/03)
-
- Ketones to amides via a formal Beckmann rearrangement in 'one pot': A solvent-free reaction promoted by anhydrous oxalic acid. Possible analogy with the Schmidt reaction
-
A variety of ketones can be directly converted into the secondary amides expected from a Beckmann rearrangement of the corresponding oximes in high yield, by heating them with hydroxylamine hydrochloride and anhydrous oxalic acid at ~100°C for 4-12 h. (Aromatic aldehydes afforded mixtures of nitrile and amide.) The transformation is apparently (kinetically) driven by the coupled decomposition of oxalic acid (to CO+CO2) via the fragmentation of an intermediate oxime mono-oxalate. However, an alternative pathway, mechanistically analogous to the Schmidt reaction, is not only equally likely but may well be general for the Beckmann rearrangement.
- Chandrasekhar, Sosale,Gopalaiah, Kovuru
-
p. 7437 - 7439
(2007/10/03)
-
- Niobium pentachloride promoted conversion of carboxylic acids to carboxamides: Synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures
-
A practical method for the conversion of carboxylic acids to the corresponding carboxamides mediated by niobium pentachloride under mild conditions is described. The synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures was accomplished via benzylic lithiation of N-methyl-3,4-dimethoxy-2-(4′-methoxybenzyl)benzamide.
- Nery, Marcelo S.,Ribeiro, Renata P.,Lopes, Claudio C.,Lopes, Rosangela S. C.
-
p. 272 - 276
(2007/10/03)
-
- Beckmann rearrangement of ketoximes on solid metaboric acid: A simple and effective procedure
-
When ketoximes admixed with solid metaboric acid (formed from boric acid at 100°C/0.1 Torr) are heated (~140°C/7-42 h), the corresponding amides or lactams are produced in excellent yields (62-92%) via the Beckmann reaction. Aromatic aldoximes undergo both dehydration to the nitrile as well as (non-stereospecific) rearrangement under the above conditions. The absence of solvent, and the mildness and low toxicity of boric acid, characterise the present procedure.
- Chandrasekhar, Sosale,Gopalaiah, Kovuru
-
p. 2455 - 2457
(2007/10/03)
-
- Studies on SRN1 Reactions. Part 6: Synthesis of 3-Methyl Derivatives of the Alkaloids Thalactamine, Doryanine, and 6,7-Dimethoxy-N-methyl-1(2H)-isoquinolone
-
A new, short synthesis of the 3-methyl derivatives (3a-c) of the alkaloids thalactamine, doryanine, and 6,7-dimethoxy-N-methyl-1(2H)-isoquinolone, based upon our previous SRN1 synthesis of isocarbostryril systems, is reported.
- Beugelmans, Rene,Ginsburg, Helene,Bois-Choussy, Michele
-
p. 1149 - 1152
(2007/10/02)
-
- ELECTRON DEFICIENT HETEROAROMATIC AMMONIOAMIDATES, XVIII. THE SYNTHESIS AND PHOTOCHEMISTRY OF SOME N-ISOQUINOLINO(THIOAMIDATES)
-
Thioacylation of isoquinolinioamide furnished the N-isoquinolinio(thioamidates) 2a-2c.Depending on the solvent, 2c exists either as a mixture with its tricyclic tautomer 5, or exclusively as the latter.The NMR and mass spectra, and the photochemistry of compounds 2a-2c are discussed.The photoproducts obtained include 3,4-dimethoxybenzonitrile, 3,4-dimethoxy(thiobenzamide), O-ethyl thiocarbamate, 1(2H)-isoquinolinethione (7a), 1(2H)-isoquinolinone (7b) and thiadiazoloisoquinolin-4-ium-2-olate (8a).Differences between the fragmentation upon electron impact and the photochemistry of the thioamidates of Types 1 and 2, as well as between the photochemistry of the thioamidates 2 and their amidate counterparts of Type 3 are discussed.Potassium permanganate oxidation of thiadiazoloisoquinolin-4-ium-2-thiolate (8b) furnishes the olate 8a and 1-isoquinolyl thiocyanate (12).
- Lempert-Sreter, M.,Lempert, K.,Tamas, J.,Vekey, K.
-
p. 259 - 270
(2007/10/02)
-