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Preparation method of acetamide compound
The invention discloses a preparation method of an acetamide compound, the preparation method comprises the following steps: reacting tetracarbonyl dichloride rhodium, 1, 3-bis (diphenylphosphine) propane, tungsten carbonyl, sodium phosphate, sodium iodide, water, a nitro compound and dimethyl carbonate at 120 DEG C for 24 hours, and after the reaction is completed, performing post-treatment to obtain the acetamide compound. According to the preparation method, dimethyl carbonate serves as a C1 source and also serves as a green solvent, operation is easy, reaction starting raw materials are low in price and easy to obtain, the tolerance range of substrate functional groups is wide, and reaction efficiency is high. Various acetamide compounds can be synthesized according to actual needs, so that the practicability of the method is widened while the operation is convenient.
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Paragraph 0035-0047

(2021/05/19)

Method for promoting acylation of amine or alcohol by carbon dioxide
The invention relates to a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.
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Paragraph 0033-0034

(2021/05/29)

Magnetically recyclable silica-coated ferrite magnetite-K10montmorillonite nanocatalyst and its applications in O, N, and S-acylation reaction under solvent-free conditions
Novel silica-coated ferrite nanoparticles supported with montmorillonite (K10) have been prepared successfully by using a simple impregnation method. Further, these nanoparticles were characterized by using different analytical methods like FT-IR, PXRD, EDS, and FE-SEM techniques. In addition, these nanoparticles have been explored for their catalytic activity for the O, N, and S-acylation reactions under solvent-free conditions which gave moderate to excellent yields in a much shorter reaction time. Moreover, these nanoparticles could easily be separated out from the reaction medium after the reaction completion by using an external magnetic field and have been re-used for 10 cycles without any significant loss of the catalytic activity.
Kumar, Pushpendra,Patil, Shripad M.,Tandon, Nitin,Tandon, Runjhun
p. 21291 - 21300
(2021/07/01)

Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation
The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.
Bényei, Attila,Domján, Attila,Egyed, Orsolya,Gonda, Zsombor,Novák, Zoltán,Sályi, Gerg?,Tóth, Balázs L.
supporting information

(2021/11/09)

Efficient nitriding reagent and application thereof
The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.
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Paragraph 0158-0160

(2021/03/31)

A novel construction of acetamides from rhodium-catalyzed aminocarbonylation of DMC with nitro compounds
Dimethyl carbonate (DMC), an environment-friendly compound prepared from CO2, shows diverse reactivities. In this communication, an efficient procedure using DMC as both a C1 building block and solvent in the aminocarbonylation reaction with nitro compounds has been developed. W(CO)6acts both a CO source and a reductant here.
Bao, Zhi-Peng,Miao, Ren-Guan,Qi, Xinxin,Wu, Xiao-Feng
supporting information
p. 1955 - 1958
(2021/03/02)

Direct para-Selective C-H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines
Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most importantly, this reaction can be easily scaled up to the ten-gram scale, highlighting its synthetic utility. The mechanistic study revealed that the in situ generated aryl hypervalent iodine intermediate is the key factor to realize this para-selective C-H amination reaction.
Chen, Yujie,Huang, Zhibin,Jiang, Yaqiqi,Shu, Sai,Yang, Shan,Shi, Da-Qing,Zhao, Yingsheng
p. 8226 - 8235
(2021/06/28)

Catalyst-free, direct electrochemical synthesis of annulated medium-sized lactams through C-C bond cleavage
A catalyst-free, direct electrochemical synthesis of synthetically challenging medium-sized lactams through C-C bond cleavage has been developed. In contrast to previous typical amidyl radical cyclization, this electrosynthetic approach enabled step-economical ring expansion through a unique remote amidyl migration under mild, metal- and external-oxidant-free conditions in a simple undivided cell. The strategy features unparalleled broad substrate scope with all ring sizes of (hetero)aryl-fused 8-11-membered rings and hetero atom-tethered rings, high yields, and good functional group tolerance. Our experimental and computational findings provided strong support for a SET-based reaction manifold.
Ackermann, Lutz,Huang, Zhixing,Kuniyil, Rositha,Li, Yueheng,Ruan, Zhixiong,Xu, Zhongnan,Zhang, Chao
supporting information
p. 1099 - 1104
(2020/03/11)

Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs
Diversity Oriented Clicking (DOC) is a unified click-approach for the modular synthesis of lead-like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease”, by combining classic C?C π-bond click chemistry with recent developments in connective SuFEx-technologies. We showcase 2-Substituted-Alkynyl-1-Sulfonyl Fluorides (SASFs) as a new class of connective hub in concert with a diverse selection of click-cycloaddition processes. Through the selective DOC of SASFs with a range of dipoles and cyclic dienes, we report a diverse click-library of 173 unique functional molecules in minimal synthetic steps. The SuFExable library comprises 10 discrete heterocyclic core structures derived from 1,3- and 1,5-dipoles; while reaction with cyclic dienes yields several three-dimensional bicyclic Diels–Alder adducts. Growing the library to 278 discrete compounds through late-stage modification was made possible through SuFEx click derivatization of the pendant sulfonyl fluoride group in 96 well-plates—demonstrating the versatility of the DOC approach for the rapid synthesis of diverse functional structures. Screening for function against MRSA (USA300) revealed several lead hits with improved activity over methicillin.
Barrow, Andrew S.,Cheng, Yunfei,Gialelis, Timothy L.,Giel, Marie-Claire,Kitamura, Seiya,Li, Gencheng,Moses, John E.,Ottonello, Alessandra,Sharpless, K. Barry,Smedley, Christopher J.,Wolan, Dennis W.
supporting information
p. 12460 - 12469
(2020/06/10)

Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles
The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.
Jiao, Ning,Liu, Jianzhong,Qiu, Xu,Song, Song,Wei, Jialiang,Wen, Xiaojin,Zhang, Cheng,Zhang, Ziyao
supporting information
p. 281 - 285
(2020/01/28)

Environmentally benign decarboxylative: N-, O-, and S-Acetylations and acylations
An operationally simple and general method for acetylation and acylation of a wide variety of substrates (amines, alcohols, phenols, thiols, and hydrazones) has been reported. Meldrum's acid and its derivatives have been used as an air-stable, non-volatile, cost-effective, and easy to handle acetylating/acylating agent. Easily separable byproducts (CO2 and acetone) allowed the isolation of analytically pure acetylated products without the requirement of work-up and any chromatography. This journal is
Ghosh, Santanu,Purkait, Anisha,Jana, Chandan K.
supporting information
p. 8721 - 8727
(2020/12/30)

Preparation method of 4-chloro-2-fluoro-5-nitroacetophenone
The invention discloses a preparation method of 4-chloro-2-fluoro-5-nitroacetophenone, the preparation method is characterized in that m-fluoroaniline is taken as an initial raw material, and the 4-chloro-2-fluoro-5-nitroacetophenone is obtained through acetylation amino protection, Friedel-Crafts acylation reaction, hydrolysis reaction, Sandmeyer reaction and final nitration, and the preparationmethod has the advantages of easily available raw materials, low reaction condition requirement, few side reactions and high yield.
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Paragraph 0019-0021

(2020/01/25)

Preparation method of hepatitis drug intermediate
The invention discloses a preparation method of a hepatitis drug intermediate, which is characterized in that m-fluoroaniline is used as an initial raw material, and subjected to acetylation amino protection, a Friedel-Crafts acylation reaction, a nitration reaction and a bromination reaction, and finally coupling is performed to obtain 1,4-bis-[(4-acetamido-2-fluoro-5-nitro)phenyl]butane-1,4-dione. According to the method, the raw materials are easy to obtain, the reaction condition requirements are low, side reactions are few, the yield is high, and the 1,4-bis-[(4-acetamido-2-fluoro-5-nitro)phenyl]butane-1,4-dione can be used as a drug intermediate for preparing pibrentasvir.
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Paragraph 0021-0022

(2020/05/08)

N-acetylation of amines in continuous-flow with acetonitrile—no need for hazardous and toxic carboxylic acid derivatives
A continuous-flow acetylation reaction was developed, applying cheap and safe reagent, acetonitrile as acetylation agent and alumina as catalyst. The method developed utilizes milder reagent than those used conventionally. The reaction was tested on various aromatic and aliphatic amines with good conversion. The catalyst showed excellent reusability and a scale-up was also carried out. Furthermore, a drug substance (paracetamol) was also synthesized with good conversion and yield.
Fül?p, Ferenc,Mándity, István M.,Orsy, Gy?rgy
(2020/04/29)

Synthesis of diverse libraries of carboxamides via chemoselective N-acylation of amines by carboxylic acids employing Br?nsted acidic IL [BMIM(SO3H)][OTf]
Chemoselective N-acylation of amines with carboxylic acids as acyl electrophiles and Br?nsted acidic IL [BMIM(SO3H)][OTf] as promoter is reported under both thermal and microwave irradiation to produce libraries of carboxamides in good to excellent yields after a simple workup. The protocol is compatible with structurally diverse 1° and 2° amines and works in the presence of sensitive functional groups such as thiols and phenols. The potential for recycling and reuse of the IL is also demonstrated.
Savanur, Hemantkumar M.,Malunavar, Shruti S.,Prabhala, Pavankumar,Sutar, Suraj M.,Kalkhambkar, Rajesh G.,Laali, Kenneth K.
supporting information

(2019/09/30)

Transition-Metal-Free C-C, C-O, and C-N Cross-Couplings Enabled by Light
Transition-metal-catalyzed cross-couplings to construct C-C, C-O, and C-N bonds have revolutionized chemical science. Despite great achievements, these metal catalysts also raise certain issues including their high cost, requirement of specialized ligands, sensitivity to air and moisture, and so-called "transition-metal-residue issue". Complementary strategy, which does not rely on the well-established oxidative addition, transmetalation, and reductive elimination mechanistic paradigm, would potentially eliminate all of these metal-related issues. Herein, we show that aryl triflates can be coupled with potassium aryl trifluoroborates, aliphatic alcohols, and nitriles without the assistance of metal catalysts empowered by photoenergy. Control experiments reveal that among all common aryl electrophiles only aryl triflates are competent in these couplings whereas aryl iodides and bromides cannot serve as the coupling partners. DFT calculation reveals that once converted to the aryl radical cation, aryl triflate would be more favorable to ipso substitution. Fluorescence spectroscopy and cyclic voltammetry investigations suggest that the interaction between excited acetone and aryl triflate is essential to these couplings. The results in this report are anticipated to provide new opportunities to perform cross-couplings.
Liu, Wenbo,Li, Jianbin,Querard, Pierre,Li, Chao-Jun
p. 6755 - 6764
(2019/05/06)

Synthesis of acetamides from aryl amines and acetonitrile by diazotization under metal-free conditions
An efficient and metal-free coupling reaction has been developed that affords acetamides from the corresponding aryl amines and acetonitrile. This method tolerates a wide range of functional groups and is selective toward aryl amines. Preliminary mechanistic studies were conducted.
Duan, Pan,Guo, Yu,Kang, Huan,Li, Yi-Na,Wen, Xianghao,Xiao, Fang,Zeng, Yao-Fu,Zhang, Na-Na
supporting information
p. 2169 - 2172
(2019/11/25)

Chagas Disease Drug Discovery: Multiparametric Lead Optimization against Trypanosoma cruzi in Acylaminobenzothiazole Series
Acylaminobenzothiazole hits were identified as potential inhibitors of Trypanosoma cruzi replication, a parasite responsible for Chagas disease. We selected compound 1 for lead optimization, aiming to improve in parallel its anti-T. cruzi activity (IC50 = 0.63 μM) and its human metabolic stability (human clearance = 9.57 mL/min/g). A total of 39 analogues of 1 were synthesized and tested in vitro. We established a multiparametric structure-activity relationship, allowing optimization of antiparasite activity, physicochemical parameters, and ADME properties. We identified compound 50 as an advanced lead with an improved anti-T. cruzi activity in vitro (IC50 = 0.079 μM) and an enhanced metabolic stability (human clearance = 0.41 mL/min/g) and opportunity for the oral route of administration. After tolerability assessment, 50 demonstrated a promising in vivo efficacy.
Fleau, Charlotte,Padilla, Angel,Miguel-Siles, Juan,Quesada-Campos, Maria T.,Saiz-Nicolas, Isabel,Cotillo, Ignacio,Cantizani Perez, Juan,Tarleton, Rick L.,Marco, Maria,Courtemanche, Gilles
supporting information
p. 10362 - 10375
(2019/11/29)

Sulfonium Salts as Alkylating Agents for Palladium-Catalyzed Direct Ortho Alkylation of Anilides and Aromatic Ureas
A novel method for the ortho alkylation of acetanilide and aromatic urea derivatives via C-H activation was developed. Alkyl dibenzothiophenium salts are considered to be new reagents for the palladium-catalyzed C-H activation reaction, which enables the transfer of methyl and other alkyl groups from the sulfonium salt to the aniline derivatives under mild catalytic conditions.
Simkó, Dániel Cs.,Elekes, Péter,Pázmándi, Vivien,Novák, Zoltán
supporting information
p. 676 - 679
(2018/02/09)

Copper-(II) Catalyzed N-Formylation and N-Acylation of Aromatic, Aliphatic, and Heterocyclic Amines and a Preventive Study in the C-N Cross Coupling of Amines with Aryl Halides
A Cu-(II) catalyzed N-formylation and N-acylation of amines with moderate to excellent yields, using N, N-dimethyl formamide (DMF) and N, N-dimethyl acetamide (DMA) as a formyl and acylating sources in the presence of 1,2,4-triazole is reported. This novel, highly efficient and simple protocol shows broad substrate scope for aliphatic, aromatic, and heterocyclic amines. In addition, the conditions to prevent N-formylation and N-acylation impurities in the C?N cross coupling of amines and aryl halides are described typically when DMF and DMA are used as solvents, with various catalysts, ligands, and bases.
Sonawane, Rahul B.,Rasal, Nishant K.,Bhange, Dattatraya S.,Jagtap, Sangeeta V.
p. 3907 - 3913
(2018/09/12)

Manganese-Catalyzed Direct Conversion of Ester to Amide with Liberation of H2
A simple and efficient Mn-catalyzed acylation of amines is achieved using both acyl and alkoxy functions of unactivated esters with the liberation of molecular hydrogen as a sole byproduct. The present protocol provides an atom-economical and sustainable route for the synthesis of amides from esters by employing an earth-abundant manganese salt and inexpensive phosphine-free tridentate ligand.
Mondal, Akash,Subaramanian, Murugan,Nandakumar, Avanashiappan,Balaraman, Ekambaram
supporting information
p. 3381 - 3384
(2018/06/11)

Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides
A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.
Das, Riki,Kapur, Manmohan
p. 1114 - 1126
(2018/06/18)

Efficient Heterogeneous Gold(I)-Catalyzed Direct C(sp2)–C(sp) Bond Functionalization of Arylalkynes through a Nitrogenation Process to Amides
The first heterogeneous gold(I)-catalyzed direct C(sp2)–C(sp) bond functionalization of arylalkynes through a nitrogenation process to amides has been achieved by using an ordered mesoporous silica (MCM-41)-immobilized phosphine gold(I) complex [MCM-41-PPh3-AuCl] as catalyst and silver carbonate (Ag2CO3) as cocatalyst with trimethylsilyl azide (TMSN3) as a nitrogen source, yielding a variety of amides in moderate to excellent yields under mild conditions. This heterogeneous phosphine gold(I) complex shows the same turnover numbers as the homogeneous chloro(triphenylphosphine)gold(I) (Ph3PAuCl) and can easily be recovered by simple filtration of the reaction solution and recycled at least eight times without significant loss of activity, providing a novel, efficient, practical and economic method for the synthesis of amides from alkynes. (Figure presented.).
Nie, Quan,Yi, Feiyan,Huang, Bin,Cai, Mingzhong
p. 3968 - 3976
(2017/11/20)

Nickel-(II)-Catalyzed N-Formylation and N-Acylation of Amines
A highly efficient protocol of Ni(II) metal complex, [Ni(quin)2], catalyzing N-formylation and N-acylation of amines with moderate to excellent yields, using N,N-dimethylformamide and N,N-dimethylacetamide in the presence of imidazole, is described here. The protocol shows broad substrate scope for aliphatic, aromatic, and heterocyclic amines.
Sonawane, Rahul B.,Rasal, Nishant K.,Jagtap, Sangeeta V.
supporting information
p. 2078 - 2081
(2017/04/28)

Combining Eosin y with Selectfluor: A Regioselective Brominating System for Para-Bromination of Aniline Derivatives
A mild, metal-free, and absolutely para-selective bromination of aniline derivatives has been developed in excellent yields, wherein the organic dye Eosin Y is employed as the bromine source in company with Selectfluor. Neither air nor moisture sensitive, this facile reaction proceeds smoothly at room temperature and completes within a short time. Mechanistic studies indicate a radical pathway; therefore, the existence of an in situ generated brominating reagent, "Selectbrom", is postulated, which may reasonably account for the unique regioselectivity for the para-bromination of N-acyl- as well as N-sulfonylanilines.
Huang, Binbin,Zhao, Yating,Yang, Chao,Gao, Yuan,Xia, Wujiong
supporting information
p. 3799 - 3802
(2017/07/26)

Mild and efficient palladium-catalyzed direct trifluoroethylation of aromatic systems by C-H activation
The introduction of trifluoroalkyl groups into aromatic molecules is an important transformation in the field of organic and medicinal chemistry. However, the direct installation of fluoroalkyl groups onto aromatic molecules still represents a challenging and highly demanding synthetic task. Herein, a simple trifluoroethylation process that relies on the palladium-catalyzed C-H activation of aromatic compounds is described. With the utilization of a highly active trifluoroethyl(mesityl)iodonium salt, the developed catalytic method enables the first highly efficient and selective trifluoroethylation of aromatic compounds. The robust catalytic procedure provides the desired products in up to 95 % yield at 25 °C in 1.5 to 3 hours and tolerates a broad range of functional groups. The utilization of hypervalent reagents opens new synthetic possibilities for direct alkylations and fluoroalkylations in the field of transition-metal-catalyzed C-H activation.
T?th, Balázs L.,Kovács, Szabolcs,Sályi, Gerg?,Novák, Zoltán
supporting information
p. 1988 - 1992
(2016/02/18)

HIGH WET FAST DISPERSE DYES AND MIXTURES THEREOF
Dyes of formula (1), their production and their use.
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Page/Page column 14

(2016/04/20)

Selective N-acetylation of aromatic amines using acetonitrile as acylating agent
A method for N-acetylation of amines has been developed using acetonitrile as an acylating agent and in situ generated trimethylsilyl iodide as the catalyst under microwave heating condition. The reaction is selective toward aromatic amines while aliphatic amines remain intact. The process eliminates the requirement of toxic acylating reagents like acetic anhydride and acetyl chloride.
Saikia, Ujwal Pratim,Hussain, Farhaz L.,Suri, Mrinaly,Pahari, Pallab
supporting information
p. 1158 - 1160
(2016/03/09)

IODINE(III)-MEDIATED RADIOFLUORINATION
A process for fluorination of aromatic compounds employing iodonium ylides and applicable to radiofluorination using 18F is described. Processes, intermediates, reagents and radiolabelled compounds are described.
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(2015/09/28)

Acetamidoarenediazonium Salts: Opportunities for Multiple Arene Functionalization
Unlike their ortho counterparts, meta- and para-acetamidoanilines can be converted into the corresponding acetamidoarenediazonium salts. These offer various opportunities for multiple Pd-catalyzed arene functionalization reactions, such as Matsuda-Heck-, Suzuki-Miyaura- or Fujiwara-Moritani couplings. Acetamidoarenediazonium salts, accessible from simple acetamidoanilines, are starting points for multiple Pd-catalyzed arene functionalization reactions.
Schmidt, Bernd,Elizarov, Nelli,Riemer, Nastja,H?lter, Frank
p. 5826 - 5841
(2015/09/15)

Palladium-catalyzed C-H bond acylation of acetanilides with benzylic alcohols under aqueous conditions
Palladium-catalyzed dehydrogenative coupling reactions between acetanilides and benzylic alcohols under aqueous conditions are reported. A wide range of benzophenone derivatives could be obtained in good to excellent yields up to 98 %. Mechanism studies showed that a bimetallic palladium cyclopalladated complex might be involved in the catalysis.
Luo, Feihua,Yang, Jun,Li, Zhengkai,Xiang, Haifeng,Zhou, Xiangge
p. 2463 - 2469
(2015/04/22)

A metal-free approach for transamidation of amides with amines in aqueous media
An efficient, environmentally benign and a mild protocol for transamidation of amides with a variety of amines in the presence of K2S2O8 using stoichiometric quantity in aqueous conditions has been established. This method works under conventional thermal conditions and in microwave irradiation as well. A series of amides have been prepared using this reaction and this is a greener protocol for transamidation, which offers a diverse kind of substrate scope with exclusive product formation (yields 90-98%).
Srinivas, Mahesuni,Hudwekar, Abhinandan D.,Venkateswarlu, Vunnam,Reddy, G. Lakshma,Kumar, K. A. Aravinda,Vishwakarma, Ram A.,Sawant, Sanghapal D.
supporting information
p. 4775 - 4779
(2015/07/20)

SPIRO-SUBSTITUTED OXINDOLE DERIVATIVES HAVING AMPK ACTIVITY
The present invention relates to compounds of formula (I), which have valuable pharmacological properties, in particular are activators of AMPK and which are therefore useful in the treatment of certain disorders that can be prevented or treated by activation of this receptor. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.
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Page/Page column 97

(2015/01/07)

A one-pot process for palladium catalyzed direct C-H acylation of anilines in water using a removable ortho directing group
A new mild, practical method for the synthesis of aminobenzophenone derivatives through a three step one-pot reaction sequence involving acylation of anilines, palladium catalyzed cross-dehydrogenative coupling of the formed anilides and the hydrolytic cleavage is reported. The full reaction sequence was performed under aqueous conditions.
Szabo, Fruzsina,Simko, Daniel,Novak, Zoltan
p. 3883 - 3886
(2014/01/06)

Pd-Catalyzed C-H activation/oxidative cyclization of acetanilide with norbornene: Concise access to functionalized indolines
An efficient Pd-catalyzed oxidative cyclization reaction for the synthesis of functionalized indolines by direct C-H activation of acetanilide has been developed. The norbornylpalladium species formed via direct ortho C-H activation of acetanilides is supposed to be a key intermediate in this transformation. This journal is the Partner Organisations 2014.
Gao, Yang,Huang, Yubing,Wu, Wanqing,Huang, Kefan,Jiang, Huanfeng
supporting information
p. 8370 - 8373
(2014/07/22)

Assessment of mycobacterium tuberculosis pantothenate kinase vulnerability through target knockdown and mechanistically diverse inhibitors
Pantothenate kinase (PanK) catalyzes the phosphorylation of pantothenate, the first committed and rate-limiting step toward coenzyme A (CoA) biosynthesis. In our earlier reports, we had established that the type I isoform encoded by the coaA gene is an essential pantothenate kinase in Mycobacterium tuberculosis, and this vital information was then exploited to screen large libraries for identification of mechanistically different classes of PanK inhibitors. The present report summarizes the synthesis and expansion efforts to understand the structure-Activity relationships leading to the optimization of enzyme inhibition along with antimycobacterial activity. Additionally, we report the progression of two distinct classes of inhibitors, the triazoles, which are ATP competitors, and the biaryl acetic acids, with a mixed mode of inhibition. Cocrystallization studies provided evidence of these inhibitors binding to the enzyme. This was further substantiated with the biaryl acids having MIC against the wild-type M. tuberculosis strain and the subsequent establishment of a target link with an upshift in MIC in a strain overexpressing PanK. On the other hand, the ATP competitors had cellular activity only in a M. tuberculosis knockdown strain with reduced PanK expression levels. Additionally, in vitro and in vivo survival kinetic studies performed with a M. tuberculosis PanK (MtPanK) knockdown strain indicated that the target levels have to be significantly reduced to bring in growth inhibition. The dual approaches employed here thus established the poor vulnerability of PanK in M. tuberculosis.
Reddy, B. K. Kishore,Landge, Sudhir,Ravishankar, Sudha,Patil, Vikas,Shinde, Vikas,Tantry, Subramanyam,Kale, Manoj,Raichurkar, Anandkumar,Menasinakai, Sreenivasaiah,Mudugal, Naina Vinay,Ambady, Anisha,Ghosh, Anirban,Tunduguru, Ragadeepthi,Kaur, Parvinder,Singh, Ragini,Kumar, Naveen,Bharath, Sowmya,Sundaram, Aishwarya,Bhat, Jyothi,Sambandamurthy, Vasan K.,Bj?rkelid, Christofer,Jones, T. Alwyn,Das, Kaveri,Bandodkar, Balachandra,Malolanarasimhan, Krishnan,Mukherjee, Kakoli,Ramachandran, Vasanthi
p. 3312 - 3326
(2014/06/09)

Oxidative para- Triflation of acetanilides
Direct triflation of acetanilide derivatives with silver triflate has been accomplished under mild iodine(III)-mediated oxidative conditions. The reaction shows excellent regioselectivity for the para position and tolerates a range of ortho and meta substituents on the aromatic ring. This method is also compatible with the preparation of arylnonaflates in synthetically useful yields.
Pialat, Amelie,Liegault, Benoit,Taillefer, Marc
supporting information
p. 1764 - 1767
(2013/06/26)

Mild palladium-catalyzed oxidative direct ortho-C-H acylation of anilides under aqueous conditions
Palladium-catalyzed cross-dehydrogenative coupling between anilides and aromatic aldehydes was achieved under aqueous conditions. A wide variety of the desired benzophenone derivatives was isolated in good to excellent yield. The reaction rate acceleration effect of acid and detergent has been demonstrated. Mechanistic insight has been obtained from quantum chemical calculations. Copyright
Szabo, Fruzsina,Daru, Janos,Simko, Daniel,Nagy, Tibor Zs.,Stirling, Andras,Novak, Zoltan
supporting information
p. 685 - 691
(2013/04/10)

H2O2-mediated oxidative formation of amides from aromatic amines and 1,3-diketones as acylation agents via C-C bond cleavage at room temperature in water under metal-free conditions
1,3-Diketones, as novel acylation agents, reacted with aromatic amines promoted by commercially available H2O2 (30% aq.) as the sole oxidant at room temperature under metal-free conditions in water, leading to a novel and rapid amide bond formation strategy. The reported method is high-yielding, simple and mild, and is the first example of the use of 1,3-diketones as acylation agents via C-C bond cleavage.
Sun, Xi,Wang, Min,Li, Pinhua,Zhang, Xiuli,Wang, Lei
supporting information
p. 3289 - 3294
(2013/12/04)

Quantitative insights into energy contributions of intermolecular interactions in fluorine and trifluoromethyl substituted isomeric N-phenylacetamides and N-methylbenzamides
The presence of the C-F bond in organic molecules, particularly in the context of generating different intermolecular interactions of the type C-F...F-C, C-H...F and C-F...π is of extreme significance in the realm of structural chemistry. These interactions generate different packing motifs in the formation of the crystal. It is of interest to evaluate the energetic contributions of such weak interactions to evaluate their important role in crystal packing. In this respect, a library of twelve compounds containing a strong donor and acceptor, along with the presence of a C-F bond in different electronic environments (fluorine atom connected to C(sp2) and C(sp3) carbon atom) have been synthesized and characterized using single crystal X-ray diffraction studies at low temperature. In addition, the non-fluorinated counterpart has also been synthesized. These crystal structures have been analyzed to understand the contribution of weak interactions involving organic fluorine in the crystal packing. Furthermore, the stabilizing-destabilizing roles of such interactions in terms of favourable energetics have been quantified with inputs from calculations performed using PIXEL. It is observed that most of the interactions involving fluorine are of a dispersive character, and in some cases the interaction is also coulombic in origin. These results have been compared with ab initio quantum-chemical calculations (DFT-D3/B-97D level) performed using TURBOMOLE. In addition, the lattice energies of all the compounds have been evaluated, and the total contribution partitioned into the corresponding coulombic, polarization, dispersion and exchange contributions using the CLP module. The results correlate well with thermochemical data experimentally determined for these compounds.
Panini, Piyush,Chopra, Deepak
p. 3711 - 3733
(2013/07/26)

Continuous flow synthesis of secondary amides by tandem azidation-amidation of anilines
The continuous flow synthesis of a variety of secondary amides by tandem azidation-amidation of anilines is described. This new procedure benefits from the improved safety feature of generating aromatic azides in flow, thus ensuring low concentrations of any potentially hazardous intermediates. The protocol was amenable to the production of multi-gram quantities of the amide product. Georg Thieme Verlag Stuttgart · New York.
Spiteri, Christian,Moses, John E.
experimental part
p. 1546 - 1548
(2012/08/07)

Synthesis and antimalarial activity of Baylis-Hillman adducts from substituted 2-chloroquinoline-3-carboxaldehydes
Various quinoline carboxaldehydes were prepared from corresponding anilides using classical Vilsmeier-Haack reaction conditions and transformed into their Baylis-Hillman adducts. The synthesized Baylis-Hillman adducts were screened for their in vitro antimalarial activity against Plasmodium falciparum . Most of the compounds out of 21 compounds synthesized and screened exhibited substantial antimalarial activity. by Walter de Gruyter.
Srihari, Ejjirothu,Kumar, Gangala Siva,Kumar, Chebolu Naga Sesha Sai Pavan,Seth, Ratnesh Kumar,Biswas, Sukla,Sridhar, Balasubramanian,Rao, Vaidya Jayathirtha
scheme or table
p. 111 - 119
(2011/11/30)

Synthesis of platensimycin analogues and their antibiotic potency
Platensimycin is a natural product isolated from various strains of Streptomyces platensis which exhibits antimicrobial activity against Gram positive bacteria, including vancomycin- and linezolide-resistant species. Analogues of platensimycin were synthesized from 3-aminobenzoic acid or other aniline derivatives and several alkyl- and aryl-carboxylic acids. The resulting compounds were tested in an agar diffusion assay against several bacteria and fungi.
Krauss, Juergen,Knorr, Veronika,Manhardt, Vera,Scheffels, Stefanie,Bracher, Franz
experimental part
p. 386 - 392
(2009/04/16)

Electrochemical fluorination of benzamide and acetanilide in anhydrous HF and in acetonitrile
Electrochemical fluorination of benzamide in anhydrous hydrogen fluoride does not involve the amide group but occurs exclusively at the aromatic ring, yielding isomeric fluoro- and difluorobenzamides and 3,3,6,6-tetrafluoro-1,4- cyclohexadienecarboxamide.
Shainyan,Danilevich,Grigor'eva,Chuvashev
p. 513 - 517
(2007/10/03)

Indium-mediated one-pot reductive conversion of nitroarenes to N-arylacetamides
N-Arylacetamides were prepared in excellent yields from nitroarenes in the presence of acetic anhydride, acetic acid and indium by a one-pot procedure.
Kim, Byeong Hyo,Han, Rongbi,Piao, Fengyu,Jun, Young Moo,Baik, Woonphil,Lee, Byung Min
p. 77 - 79
(2007/10/03)

Anisotropic organic compounds
STR1 The invention describes liquid crystalline compounds or formula (I), where A, D and G are independently selected from phenyl, thiophene, hydrogenated phenyl, chlorinated phenyl and fluorinated phenyl, B and E are independently selected from a single bond C= C. C C.C00, azoxy and diazo, k and m are independently selected from 1 and 0, such that m+n is 1 or 2, and R1 and R2 are independently selected from R, R0, alkynyl, thioalkyl, hydrogen, CN, NCS and SCN; provided that at least one of R1 and R2 is selected from CN, NCS and SCN and that at least one of A, D and G is phenyl; and excluding where at least one of R1 and R2 is independently selected as CN and one of A, D or G is not thiophene, and where m is 0, A, and D are phenyl, B is a single bond and only one of R1 or R2 is NCS. Also described are compounds suitable for inclusion in a device utilizing pretransitional characteristics of liquid crystalline materials in the isotropic phase, of general formula (II) where J and Y are independently selected from phenyl, thiophene, hydrogenated phenyl, chlorinated phenyl and fluorinated phenyl, X is selected from C= C. C C.COO azoxy and diazo, k is 1 or 0 and R3 and R4 are independently selected from R, RO, alkynyl, thioalkyl, hydrogen, CN, NCS and SCN; provided that at least one of R3 and R4 is selected from CN, NCS and SCN and that at least one of J and Y is phenyl.
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(2008/06/13)

Long-range intrinsic and equilibrium deuterium isotope effects on 19F chemical shifts
Deuterium isotope effects on 19F chemical shifts caused by deuteriation at OH or NH groups have been determined for intramolecularly hydrogen bonded compounds including fluorinated o-hydroxyacyl aromatics, enaminones, o-hydroxyazo and hydrazo compounds. The o-hydroxyazo and hydrazo compounds represent tautomeric and non-tautomeric cases. Deuterium isotope effects on fluorine chemical shifts for o-hydroxyacyl aromatics are found to parallel deuterium isotope effects at the carbon ipso to fluorine. For the azo and hydrazo compounds very long-range effects are seen formally over ten bonds. Throughspace effects are observed in the case of spatially close nuclei like 2-fluorobenzamide-N-α. The isotope effects on 19F chemical shifts can, in p-fluorophenyl substituted cases, be used to monitor the change in equilibrium upon deuteriation and therefore to estimate the importance of hydrogen bonds. Acta Chemica Scandinavica 1997.
Hansen, Poul Erik,Bolvig, Simon,Buvari-Barcza, Agnes,Lycka, Antonin
p. 881 - 888
(2007/10/03)

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In connection with our work on styryl derivatives of benzodiazinones, we have prepared the 7-N, N-dimethylamino-3-methyl-l , 4-benzodiazin-2-one 4a and two chromo-and fluoroionophores derived from the monoaza-15-crown-5 and styrylbenzodiazinones. A structural study of these compounds by 1H and l3C NMR, UV spectrophotometry, and molecular modelling was carried out. Unlike styrylbenzoxazinones, styrylbenzodiazinone derivatives showed a Z/E isomerization in acetonitrile solution. The isomerization was photoinduced, was catalysed by metallic ions, and was a reversible process. As well, an efficient alkylation reaction of the lactam function of benzodiazinones is described.
Cazaux, Louis,Faher, Mourad,Picard, Claude,Tisnes, Pierre
p. 1236 - 1246
(2007/10/02)

The Synthesis of Several Lateral Difluoro-substituted 4,4''-Dialkyl- and 4,4''-Alkoxyalkyl-Terphenyls and a Rationalisation of the Effect of Such Substitution on Mesophase Type and Transition Temperatures
In recent years we have prepared a large number of mono-fluoro- and ortho-difluoro-substituted 4,4''-dialkyl- and 4,4''-alkoxyalkyl-terphenyls.The synthesis and transition temperatures of a variety of related difluoro compounds is presented here so that it is now possible to identify (i) broadening of the molecule, (ii) twisting about an inter-annular bond, and (iii) the presence of an "inner" (2-, 2'-, 3'- or 2''-substituent) or an "outer" (3- or 3''-substituent) fluorine, as being the major factors which influence the type and the thermal stability of the mesophases obtained.
Gray, G. W.,Hird, M.,Toyne, K. J.
p. 43 - 64
(2007/10/02)

o-Nitroaniline Derivatives. Part 9. Benzimidazole N-Oxides Unsubstituted at N-1 and C-2
Since previous routes to the title compounds (1) have proved unsatisfactory as general methods, a simple new synthesis has been devised.N-Cyanomethyl-o-nitroanilines (5) are cyclised in basic media, giving 2-cyanobenzimidazole N-oxides (12) in good yield.Hydrolysis of these products with hydrochloric acid gives, directly, the title compounds as their hydrochloride salts (13), which may be isolated and purified, and which give the free N-oxides (1) by treatment with aqueous ammonia followed by evaporation. o-Nitrophenylglycine esters (4) may satisfactorily replace the nitriles (5) in certain cases.A modification of this kind in the related nitropyridylglycine series leads to 3H-imidazolpyridine 1-oxide (20).
Harvey, Ian W.,McFarlane, Michael D.,Moody, David J.,Smith, David M.
p. 681 - 690
(2007/10/02)