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Route to pyrrolo[1,2-a]quinoxalines via a furan ring opening-pyrrole ring closure sequence
A method was developed for the synthesis of pyrrolo[1,2-a]quinoxalines based on an acid-promoted furan ring opening of readily accessible N-(furan-2-ylmethyl)-2-nitroanilines or their heterocyclic analogues followed by a key reductive Paal-Knorr cyclization of the corresponding nitro-1,4-diketones.
Nevolina, Tatyana A.,Skvortsov, Dmitry A.,Sorotskaja, Ludmila N.,Trushkov, Igor V.,Uchuskin, Maxim G.,Zelina, Elena Y.
(2019)
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Synthesis, structural determination, Hirshfeld surface analysis, 3D energy frameworks, electronic and (static, dynamic) NLO properties of o-Nitroacetanilide (o-NAA): A combined experimental and quantum chemical study
o-Nitroacetanilide (o-NAA), an organic crystal, was synthesized and fully characterized by means of single-crystal XRD, FTIR, UV–visible,1H and 13C NMR spectroscopic techniques. Its molecular structure was optimized, the subsequent electronic properties, the spectroscopic spectra were quantified using quantum chemical computations by density functional theory calculations and compared with the experimental results. Furthermore, the Mulliken atomic charges were estimated andthe molecular electrostatic potential map was plotted in order to identify the chemical reactive sites. To study the nonlinear optical (NLO) activity of o-NAA, the electric dipole moment, the static and dynamic polarizability and hyperpolarizabilities were computed indicating that it could be considered as a good candidate for NLO applications. The hydrogen bonding and the non-classical intermolecular interactions were investigated by performing a Hirshfeld surface analysis and their contributions were analyzed via the 2D-Fingerprint plots, thus revealing that the crystal structure of the studied molecule is mainly built up of H…H, H…O/O…H, H…C/C…H and C…O/O…C close contacts. From the 3D-molecular energy frameworks analysis, the lattice energy of the compound was found to be ? 95.15 kJ.mol?1, and has exhibited stabilizing strong C[sbnd]H…O, N[sbnd]H…C, lp…lp, lp…π and π…π interactions.
Boukabcha, Nourdine,Chouaih, Abdelkader,Dege, Necmi,Direm, Amani,Drissi, Mokhtaria,Khelloul, Nawel,Megrouss, Youcef,Tuna, Murat
(2021/09/07)

Preparation and catalytic evaluation of a palladium catalyst deposited over modified clinoptilolite (Pd&at;MCP) for chemoselective N-formylation and N-acylation of amines
Novel palladium nanoparticles stabilized by clinoptilolite as a natural inexpensive zeolite prepared and used for N-formylation and N-acylation of amines at room temperature at environmentally benign reaction conditions in good to excellent yields. Pd (II) was immobilized on the surface of clinoptilolite via facile multi-step amine functionalization to obtain a sustainable, recoverable, and highly active nano-catalyst. The structural and morphological characterizations of the catalyst carried out using XRD, FT-IR, BET and TEM techniques. Moreover, the catalyst is easily recovered using simple filtration and reused for 7 consecutive runs without any loss in activity.
Amirsoleimani, Mina,Khalilzadeh, Mohammad A.,Zareyee, Daryoush
(2020/08/22)

An organocatalytic C-C bond cleavage approach: A metal-free and peroxide-free facile method for the synthesis of amide derivatives
A facile organocatalytic approach has been devised towards the synthesis of amide derivatives using 1,3-dicarbonyls as easily available acyl-sources under peroxide-free reaction conditions. This transformation was accomplished by the cleavage of the C-C bond in the presence of TEMPO as an organocatalyst and excludes the use of transition-metals and harsh reaction conditions. A broad range of substrates with diverse functional groups were well tolerated and delivered the products in high yields.
Vodnala, Nagaraju,Gujjarappa, Raghuram,Polina, Saibabu,Satheesh, Vanaparthi,Kaldhi, Dhananjaya,Kabi, Arup K.,Malakar, Chandi C.
supporting information
p. 20940 - 20944
(2020/12/31)

New half-sandwich (η6-p-cymene)ruthenium(II) complexes with benzothiazole hydrazone Schiff base ligand: Synthesis, structural characterization and catalysis in transamidation of carboxamide with primary amines
Few half-sandwich (η6-p-cymene) ruthenium(II) complexes supported by benzothiazole hydrazone Schiff bases were synthesized. The new complexes possess the general formulae [Ru(η6-p-cymene)(L)Cl] (1-3) (L = salicyl((2-(benzothiazol-2-yl)hydrazono)methylphenol) (SAL-HBT), 2-((2-(benzothiazol-2-yl)hydrazono)methyl)-6 methoxyphenol) (VAN-HBT) or naphtyl-2-((2-(benzothiazol-2-yl)hydrazono)methyl phenol) (NAP-HBT). All compounds were fully studied by analytical, spectroscopic techniques (IR, NMR) and also by mass spectrometry. The solid state structure of the complex 3 reveals the coordination of p-cymene moieties with ruthenium(II) in a three-legged piano-stool geometry along with benzothiazole hydrazone Schiff base ligand in a monobasic bidentate fashion. The catalytic properties of the complexes were screened in transamidation of primary amide with amines after optimization with respect to solvent, substituents, time and catalyst loading. The results show that the complex 3 is the most efficient catalyst for the transamidation of carboxamides with amines.
Vijayapritha, Subbarayan,Viswanathamurthi, Periasamy
supporting information

(2020/10/18)

Transition-metal-free mono- or dinitration of protected anilines
An amide-assisted arene nitration is presented, and both mono- and dinitration of protected anilines could be effected by using NaNO2 and NaNO3 as the mono- and bisnitrating agents, respectively. This divergent synthesis is transition-metal- and acid-free, and features a broad substrate scope, low cost, and ortho–para selectivity.
Dai, Enrui,Dong, Ying,Dong, Yongrui,Kong, Rui,Liang, Deqiang,Liu, Guangzhang,Ma, Yinhai,Wu, Qiong
(2020/04/27)

SO2F2-Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams
A novel, mild and practical protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available and economical sulfuryl fluoride (SO2F2 gas) has been developed. The substrate scope of the operationally simple methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields (over 90 % yield in most cases) in a short time, including B(OH)2, COOH, NH2, and OH substituted substrates. A tentative mechanism was proposed involving formation and elimination of key intermediate, sulfonyl ester.
Zhang, Guofu,Zhao, Yiyong,Xuan, Lidi,Ding, Chengrong
supporting information
p. 4911 - 4915
(2019/07/31)

Copper-Catalyzed Site-Selective Oxidative C?C Bond Cleavage of Simple Ketones for the Synthesis of Anilides and Paracetamol
A copper-catalyzed approach for the N-acylation of anilines with acetone and acetophenones via C?C bond cleavage is described. Under the developed conditions both CHCl3 and CH2Cl2 were identified as potential C1-source to promote the transformation. The reaction features a site selective C?C bond cleavage to install the amide moieties with high functional-group compatibility and wide substrate scope. The developed method avoids the use of sensitive and narcotic agents. The method also represents an excellent complement to the previous protocols with lower E-factor (13.91 mg/1 mg) than current industrially used method (E-factor 17.54 mg/1 mg). The developed approach has also been extended for the effective preparation of pyridine derivatives and paracetamol in gram scale. The course of the reaction was monitored by 1H NMR as a preliminary investigation of the reaction mechanism. (Figure presented.).
Vodnala, Nagaraju,Gujjarappa, Raghuram,Hazra, Chinmoy K.,Kaldhi, Dhananjaya,Kabi, Arup. K.,Beifuss, Uwe,Malakar, Chandi C.
supporting information
p. 135 - 145
(2018/12/05)

3-(Ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium cation: A green alternative to tert-butyl nitrite for synthesis of nitro-group-containing arenes and drugs at room temperature
Due to their remarkable properties, task-specific ionic liquids have turned out to be progressively popular over the last few years in the field of green organic synthesis. Herein, for the first time, we report that a new task-specific nitrite-based ionic liquid such as 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imides (TS-N-IL) derived from biodegradable ethyl nicotinate indeed acted as an efficient and eco-friendly reagent for the synthesis of highly valuable nitroaromatic compounds and drugs including nitroxynil, tolcapone, niclofolan, flutamide, niclosamide and nitrazepam. The bridging of an ionic liquid with nitrite group not only increases the yield and rate of direct C[sbnd]N bond formation reaction but also allows easy product separation and recyclability of a byproduct. Nonvolatile nature, easy synthesis, merely stoichiometric need and mildness are a portion of the extra focal points of TS-N-IL while contrasted with tert-butyl nitrite an outstanding and highly-flammable reagent utilized largely in organic synthesis.
Chaudhary, Renu,Natarajan, Palani,Rani, Neetu,Sakshi,Venugopalan, Paloth
supporting information

(2019/12/30)

Conformational analysis of N-aryl-N-(2-azulenyl)acetamides
Aromatic amides bearing 2-azulenyl group on the amide nitrogen were synthesized and their structures were investigated. The π-electron density of the N-aryl group was found to influence the cis-trans conformational preferences of these compounds in solution. X-ray crystallography revealed that the plane of the 2-azulenyl ring has a strong tendency to lie coplanar with the amide plane when the azulene group is located on the same side as the amide oxygen atom.
Ito, Ai,Amaki, Takamasa,Ishii, Ayako,Fukuda, Kazuo,Yamasaki, Ryu,Okamoto, Iwao
supporting information
p. 3994 - 3998
(2018/10/02)

Biogenic CuFe2O4 magnetic nanoparticles as a green, reusable and excellent nanocatalyst for acetylation reactions under solvent-free conditions
A convenient green method has been developed for the synthesis of biogenic CuFe2O4 magnetic nanoparticles using tea extracts within a very short reaction time. The prepared nanoparticles with an average size of 8.78 nm have been used as an effective catalyst for the acetylation of various alcohols, phenols and amines in good to excellent yields under solvent-free conditions. The catalyst was characterized by XRD, XPS, VSM, SEM and TEM study. A magnetic study of the fresh and recycled catalyst after the fourth cycle was performed by VSM measurement. The main advantages of this protocol are simple biogenic synthesis of the catalyst, a reusable and heterogeneous catalytic system, and short reaction times with excellent yields.
Chutia, Rituparna,Chetia, Bolin
p. 15200 - 15206
(2018/09/29)

Novel 8-nitroquinolin-2(1H)-ones as NTR-bioactivated antikinetoplastid molecules: Synthesis, electrochemical and SAR study
To study the antiparasitic 8-nitroquinolin-2(1H)-one pharmacophore, a series of 31 derivatives was synthesized in 1–5 steps and evaluated in vitro against both Leishmania infantum and Trypanosoma brucei brucei. In parallel, the reduction potential of all molecules was measured by cyclic voltammetry. Structure-activity relationships first indicated that antileishmanial activity depends on an intramolecular hydrogen bond (described by X-ray diffraction) between the lactam function and the nitro group, which is responsible for an important shift of the redox potential (+0.3 V in comparison with 8-nitroquinoline). With the assistance of computational chemistry, a set of derivatives presenting a large range of redox potentials (from ?1.1 to ?0.45 V) was designed and provided a list of suitable molecules to be synthesized and tested. This approach highlighted that, in this series, only substrates with a redox potential above ?0.6 V display activity toward L. infantum. Nevertheless, such relation between redox potentials and in vitro antiparasitic activities was not observed in T. b. brucei. Compound 22 is a new hit compound in the series, displaying both antileishmanial and antitrypanosomal activity along with a low cytotoxicity on the human HepG2 cell line. Compound 22 is selectively bioactivated by the type 1 nitroreductases (NTR1) of L. donovani and T. brucei brucei. Moreover, despite being mutagenic in the Ames test, as most of nitroaromatic derivatives, compound 22 was not genotoxic in the comet assay. Preliminary in vitro pharmacokinetic parameters were finally determined and pointed out a good in vitro microsomal stability (half-life > 40 min) and a 92% binding to human albumin.
Pedron, Julien,Boudot, Clotilde,Hutter, Sébastien,Bourgeade-Delmas, Sandra,Stigliani, Jean-Luc,Sournia-Saquet, Alix,Moreau, Alain,Boutet-Robinet, Elisa,Paloque, Lucie,Mothes, Emmanuelle,Laget, Michèle,Vendier, Laure,Pratviel, Geneviève,Wyllie, Susan,Fairlamb, Alan,Azas, Nadine,Courtioux, Bertrand,Valentin, Alexis,Verhaeghe, Pierre
p. 135 - 152
(2018/06/08)

Regioselective nitration of anilines with Fe(NO3)3·9H2O as a promoter and a nitro source
An efficient Fe(NO3)3·9H2O promoted ortho-nitration reaction of aniline derivatives has been developed. This reaction may go through a nitrogen dioxide radical (NO2) intermediate, which is generated by the thermal decomposition of iron(iii) nitrate. The practicality of the present method using nontoxic and inexpensive iron reagents has been shown by the broad substrate scope and applications.
Gao, Yang,Mao, Yuanyou,Zhang, Biwei,Zhan, Yingying,Huo, Yanping
supporting information
p. 3881 - 3884
(2018/06/08)

Silver-Catalyzed Chemo- and Regioselective Nitration of Anilides
A new and efficient Ag-catalyzed method for the nitration of anilides by using sodium nitrite as a cheap and available NO2 source has been developed. This C–H functionalization reaction is ortho-selective, achieves moderate to high yields and shows excellent functional group tolerance. Furthermore, it provides a novel approach to ortho-nitrated anilides, which are very tricky to access with traditional methods.
Kianmehr, Ebrahim,Nasab, Sepideh Bahrami
p. 6447 - 6452
(2018/11/01)

The synthesis of benzimidazoles via a recycled palladium catalysed hydrogen transfer under mild conditions
An efficient synthesis of benzimidazoles was developed by virtue of a recycled palladium catalyzed hydrogen transfer. The reaction can be carried out smoothly under mild conditions to give rise to a variety of benzimidazoles with good to excellent yields. The palladium catalyst could be recovered easily and reused six times with great catalytic activity.
Guan, Qianqian,Sun, Qi,Wen, Lixian,Zha, Zhenggen,Yang, Yu,Wang, Zhiyong
supporting information
p. 2088 - 2096
(2018/03/27)

Visible-Light-Mediated Nitration of Protected Anilines
The photocatalytic nitration of protected anilines proceeds with riboflavin tetraacetate as an organic photoredox catalyst. Sodium nitrite serves as the NO2 source in this visible-light-driven room temperature reaction. Various nitroanilines are obtained in moderate to good yields without the addition of acid or stoichiometric oxidation agents. The catalytic cycle is closed by aerial oxygen as the terminal oxidant.
Düsel, Simon J. S.,K?nig, Burkhard
p. 2802 - 2807
(2018/03/09)

Copper-Catalyzed Direct Nitration on Aryl C-H Bonds by Concomitant Azidation-Oxidation with TMS Azide and TBHP under Aerobic Conditions
An unprecedented copper-catalyzed in situ azidation-oxidation for the nitration of anilides and sulfonamides has been developed by direct CAr-H functionalization. This novel and efficient nitration protocol is achieved employing TMSN3 and TBHP without the exclusion of air or moisture. The synthetic applications of the 2-nitroanilides have been explored.
Vinayak, Botla,Chandrasekharam, Malapaka
supporting information
p. 3528 - 3531
(2017/07/17)

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)

Palladium(II)-catalyzed, heteroatom-directed, regioselective C-H nitration of anilines using pyrimidine as a removable directing group
A new palladium-catalyzed, heteroatom-directed strategy for C-H nitration of anilines is described. This C-H functionalization reaction is highly ortho-selective and results in very good yields. The highlight of the work is the use of pyrimidine as the removable directing group. This approach constitutes one of the rare methods of ortho-nitration of anilines, a reaction that is normally very difficult to achieve via traditional approaches.
Pawar, Govind Goroba,Brahmanandan, Abhilashamole,Kapur, Manmohan
supporting information
p. 448 - 451
(2016/02/18)

Harnessing the pyrroloquinoxaline scaffold for FAAH and MAGL interaction: Definition of the structural determinants for enzyme inhibition
This paper describes the development of piperazine and 4-aminopiperidine carboxamides/carbamates supported on a pharmacogenic pyrroloquinoxaline scaffold as inhibitors of the endocannabinoid catabolizing enzymes fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL). Structure-activity relationships and molecular modelling studies allowed the definition of the structural requirements for dual FAAH/MAGL inhibition and led to the identification of a small set of derivatives (compounds 5e, i, k, m) displaying a balanced inhibitory profile against both enzymes, with compound 5m being the frontrunner of the subset. Favorable calculated physico-chemical properties suggest further investigation for specific analogues.
Brindisi, Margherita,Brogi, Simone,Maramai, Samuele,Grillo, Alessandro,Borrelli, Giuseppe,Butini, Stefania,Novellino, Ettore,Allarà, Marco,Ligresti, Alessia,Campiani, Giuseppe,Di Marzo, Vincenzo,Gemma, Sandra
p. 64651 - 64664
(2016/07/23)

Doping of copper (I) oxide onto a solid support as a recyclable catalyst for acetylation of amines/alcohols/phenols and synthesis of trisubstituted imidazole
A study of copper-mediated C-heteroatom especially C-N and C-O bond formations using simpler methodologies has been carried out. In the present work, acetylation of various substrates such as amines, phenols and alcohols; synthesis of 2,4,5-trisubstituted imidazole is done using simple and easily available starting materials. Copper (I) oxide was synthesized in situ by the reduction of Fehling's solution with glucose followed by its anchoring onto different supports like silica, HAP, basic alumina and cellulose. Comparison and contrasts between the reactivity of copper (I) oxide supported onto different supports for these reactions are made. The reactivity of copper (I) oxide seems to be largely dependent on the nature of support and the most active catalyst for a particular reaction was further characterized by different spectroscopic techniques such as FTIR, XRD, TGA, XPS, SEM, TEM and AAS. The catalysts were found to be stable, easily recyclable without any significant loss in activity. Graphical abstract: Applications of solid supported copper (I) oxides (where solid support is silica, HAP, cellulose and basic alumina) are studied for various organic transformations with special emphasis on C-N and C-O bond formation reactions.[Figure not available: see fulltext.]
Gupta, Manjulla,Gupta, Monika
p. 231 - 241
(2016/01/09)

Folding Patterns in a Family of Oligoamide Foldamers
A series of small, unsymmetrical pyridine-2,6-dicarboxylamide oligoamide foldamers with varying lengths and substituents at the end groups were synthetized to study their conformational properties and folding patterns. The @-type folding pattern resembled the oxyanion-hole motifs of enzymes, but several alternative folding patterns could also be characterized. Computational studies revealed several alternative conformers of nearly equal stability. These folding patterns differed from each other in their intramolecular hydrogen-bonding patterns and aryl-aryl interactions. In the solid state, the foldamers adopted either the globular @-type fold or the more extended S-type conformers, which were very similar to those foldamers obtained computationally. In some cases, the same foldamer molecule could even crystallize into two different folding patterns, thus confirming that the different folding patterns are very close in energy in spite of their completely different shapes. Finally, the best match for the observed NOE interactions in the liquid state was a conformation that matched the computationally characterized helix-type fold. Erase and refold: Like peptides, oligoamide foldamers fold into a number of different conformers that are very close in energy (see picture, stability energies in kcal mol-1 given in parentheses). By using a combination of computational, single-crystal X-ray diffraction, and NMR spectroscopic studies, these folding patterns have been identified and characterized for a family of seven different foldamers with varying substituents.
Kortelainen, Minna,Suhonen, Aku,Hamza, Andrea,Pápai, Imre,Nauha, Elisa,Yliniemel?-Sipari, Sanna,Nissinen, Maija,Pihko, Petri M.
supporting information
p. 9493 - 9504
(2015/06/30)

Beckmann rearrangement of oximes using doped silica gel complex
A new complex of perchloric acid absorbed on silica gel (doped silica gel) and dichloromethane was found to be very effective for converting ketoximes into their corresponding amides or lactams with excellent conversion via the Beckmann rearrangement. This method offers significant advantages such as efficiency and mild reaction conditions with shorter reaction time.
Umanadh,Reddy, N. Srinivasa,Mukkanti, Khagga,Omprakash
p. 1209 - 1211
(2015/02/19)

Steric-Hindrance-Induced Regio- and Chemoselective Oxidation of Aromatic Amines
Unusual regio- and chemoselective oxidation of aromatic amines hindered with ortho substituents (except -NH2, -NHCH3, and -OH) to the corresponding nitro compounds is described by use of nonanebis(peroxoic acid). The mechanistic investigation for selective oxidation of amines ortho-substituted with -NH2 or -OH showed the involvement of H-bonding between the ortho hydrogen of the adjacent -XH group (where X = NH, NR, or O) and an oxygen atom from the diperoxy acid. Various mono- and diamines are oxidized into corresponding mononitro derivatives in high yield and purity without employing any protection strategies. The protocol was also found to successful on the gram scale.
Patil, Vilas Venunath,Shankarling, Ganapati Subray
p. 7876 - 7883
(2015/09/01)

Effective nitration of anilides and acrylamides by tert-butyl nitrite
Nitro compounds are important intermediates in synthetic organic chemistry and the chemical industry. Herein, the efficient copper-catalyzed [10% Cu(NO3)2·3H2O] nitration of anilides was developed by using TBN (tert-butyl nitrite) as a nitrating reagent to give the corresponding nitro-substituted aromatic products in good to excellent yields. The use of TBN also led to the selective nitration of acrylamides at room temperature to afford only the (E) isomer of the nitration product. A series of anilides and acrylamides with a broad array of functional groups were well-tolerated by this procedure. This synthetic method has many advantages, which include inexpensive starting materials, mild reaction conditions, a fast reaction rate, and high yields. A mechanistic investigation indicates that a nitro radical, which is generated from the thermal homolysis of TBN, is involved in the two nitration processes. The efficient nitration of both anilides and acrylamides was achieved by using TBN (tert-butyl nitrite) as a metal-free nitrating reagent. This synthetic method has many advantages such as mild reaction conditions, a fast reaction rate, good to excellent yields, and a broad substrate scope. Our investigation indicates that a nitro radical is involved in the reaction mechanism.
Ji, Yi-Fei,Yan, Hong,Jiang, Qi-Bai
p. 2051 - 2060
(2015/03/18)

CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acids with amides and anilines
CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acid with amide has been developed, leading to N-arylamides in modest to excellent yields. Anilines bearing electron-withdrawing substituents could also couple efficiently
Sheng, Wei-Jian,Ye, Qing,Yu, Wu-Bin,Liu, Ren-Rong,Xu, Meng,Gao, Jian-Rong,Jia, Yi-Xia
supporting information
p. 599 - 601
(2015/02/19)

The beckmann rearrangement executed by visible-light-driven generation of vilsmeier-haack reagent
A new and efficient approach for the Beckmann rearrangement is reported. The protocol involves eosin? Y catalyzed, visible-light-mediated in situ formation of the Vilsmeier-Haack reagent from CBr4 and a catalytic amount of DMF for activation of ketoximes at room temperature. The method is operationally simple and avoids the need for any corrosive, water-sensitive reagents and elevated temperatures. Georg Thieme Verlag Stuttgart New York.
Srivastava, Vishnu P.,Yadav, Arvind K.,Yadav, Lal Dhar S.
supporting information
p. 665 - 670
(2014/04/03)

A novel silver nanoparticle embedded mesoporous polyaniline (mPANI/Ag) nanocomposite as a recyclable catalyst in the acylation of amines and alcohols under solvent free conditions
A mesoporous polyaniline/silver (mPANI/Ag) nanocomposite has been prepared using mesoporous organic polymer polyaniline with silver nitrate via radical polymerization of aniline monomer in the presence of hydrochloric acid. The mPANI/Ag nanocomposite has been characterized by powder X-ray diffraction (XRD), transmission electron microscopy (TEM), energy-dispersive X-ray spectra (EDX), Fourier transform infrared spectroscopy (FT-IR), and ultraviolet-visible absorption spectra (UV-vis). The XRD patterns indicated that the crystalline phase of Ag is cubic. TEM images show that the Ag nanoparticles are well dispersed in the mesoporous polyaniline matrix. The mPANI/Ag acts as an efficient heterogeneous nanocatalyst in the acylation of substituted amines and alcohols using acetic acid. The catalyst is air-stable, inexpensive, easy to prepare and can be reused several times without a significant decrease in activity and selectivity. This journal is
Mandi, Usha,Roy, Anupam Singha,Banerjee, Biplab,Islam, Sk. Manirul
p. 42670 - 42681
(2015/02/19)

Phosphoric acid modified montmorillonite clay: A new heterogeneous catalyst for nitration of arenes
The easily available montmorillonite clay is treated with phosphoric acid and 10 wt.% is found to be the optimum concentration of phosphoric acid that can be adsorbed chemically on the surface of the clay. Acidity of this phosphoric acid treated montmorillonite clay (PAM) is determined by volumetric as well as potentiometric titration and characterized. Catalytic efficacy of PAM in nitration of various aromatic compounds is reported.
Bharadwaj, Saitanya K.,Boruah, Purna K.,Gogoi, Pradip K.
p. 124 - 128
(2014/12/11)

Regioselective ortho-nitration of N-phenyl carboxamides and primary anilines using bismuth nitrate/acetic anhydride
An efficient and one-pot synthetic method for the regioselective ortho-nitration of the N-phenyl carboxamides and primary anilines has been developed by using bismuth nitrate and acetic anhydride as the nitrating reagents. Reaction proceeds at room temperature and results in corresponding ortho-nitrated products in moderate to excellent yields. This method provides an operationally simple, regioselective, and efficient access to synthesize o-nitro anilines under the mild conditions.
Lu, Yang,Li, Yaming,Zhang, Rong,Jin, Kun,Duan, Chunying
supporting information
p. 9422 - 9427
(2013/10/08)

Lewis basic ionic liquid as an efficient and facile catalyst for acetylation of alcohols, phenols, and amines under solvent-free conditions
The Lewis basic ionic liquid 1,8-diazabicyclo[5.4.0]undec-7-en-8-ium acetate was employed for the acetylation of various phenols, alcohols, and amines in good-to-excellent yields at 50 C under solvent-free conditions in a short time. Compared with existing methods based on conventional catalysts and toxic solvents, the reported method is simple, mild and environmentally viable. Furthermore, the ionic liquid was conveniently separated from the products and easily recycled to catalyze other acetylation reactions with excellent yields. .
Ji, Li,Qian, Chao,Chen, Xin-Zhi
p. 369 - 374
(2013/05/21)

Design, synthesis and anticancer activity evaluation of diazepinomicin derivatives
A series of diazepinomicin derivatives were synthesized and evaluated in vitro for their growth inhibitory activity against the human carcinoma cell lines. The results indicated the anticancer selectivity of this kind of compounds. Based on the results, preliminary structure-activity relationships were discussed.
Yu, Yongguo,Wu, Jianbo,Lei, Fan,Chen, Lei,Wan, Weili,Hai, Li,Guan, Mei,Wu, Yong
p. 369 - 373
(2013/07/26)

Copper-promoted sandmeyer trifluoromethylation reaction
A copper-promoted trifluoromethylation reaction of aromatic amines is described. This transformation proceeds smoothly under mild conditions and exhibits good tolerance of many synthetically relevant functional groups. It provides an alternative approach for the synthesis of trifluoromethylated arenes and heteroarenes. It also constitutes a new example of the Sandmeyer reaction.
Dai, Jian-Jun,Fang, Chi,Xiao, Bin,Yi, Jun,Xu, Jun,Liu, Zhao-Jing,Lu, Xi,Liu, Lei,Fu, Yao
supporting information
p. 8436 - 8439
(2013/07/19)

Recyclable, highly efficient and low cost nano-MgO for amide synthesis under SFRC: A convenient and greener 'NOSE' approach
A clean synthesis of amide derivatives has successfully been accomplished utilizing reusable nano-MgO under 'SFRC' (solvent free reaction condition). The 'green-ness' of this protocol makes it a benign alternative for the large scale synthesis.
Das, Vijay Kumar,Devi, Rashmi Rekha,Thakur, Ashim Jyoti
p. 118 - 125
(2013/06/26)

Nano rod-shaped and reusable basic Al2O3 catalyst for N-formylation of amines under solvent-free conditions: A novel, practical and convenient 'NOSE' approach
An expeditious, simple, highly efficient, practical and green protocol for the N-formylation of alkyl/aryl amines and indole derivatives catalyzed by novel nano rod-shaped basic Al2O3 under solvent-free conditions has been developed. The catalyst is efficiently recycled up to the 5th run, an important point in the domain of green chemistry. The methodology provides cleaner conversion, shorter reaction times and high selectivity which makes the protocol attractive. The Royal Society of Chemistry 2012.
Das, Vijay Kumar,Devi, Rashmi Rekha,Raul, Prasanta Kumar,Thakur, Ashim Jyoti
supporting information; experimental part
p. 847 - 854
(2012/04/23)

Amorphous carbon-silica composites bearing sulfonic acid as solid acid catalysts for the chemoselective protection of aldehydes as 1,1-diacetates and for N-, O- and S-acylations
Amorphous carbon-silica composites bearing sulfonic acid derived from inexpensive natural organic compounds (glucose, maltose, cellulose, chitosan and starch) were prepared by partial carbonization followed by sulfonation and their catalytic activity was evaluated for the protection of aldehydes as 1,1-diacetates and for N-, O- and S-acylations under solvent-free conditions. Different biomaterials have been chosen, with a view to select the most active solid acid catalyst. Carbon-silica composites were characterized by FTIR, XRD and elemental analysis. Sulfonated carbon-silica composite derived from starch was found to be the most active and could be recycled for several runs without loss of significant activity. It was also characterized by TGA, SEM and TEM.
Gupta, Princy,Paul, Satya
experimental part
p. 2365 - 2372
(2011/10/31)

Mild and efficient nitration of aromatic compounds mediated by transitionmetal complexes
Aromatic compounds were efficiently nitrated under facile reaction conditions by employing 69% nitric acid catalyzed by transition-metal complexes such as [Co(NH3)5Cl]Cl2, [Cu(NH 3)4]SO4, Mn(acac)3, [Ni(NH 3)6]Cl2, [Ni(en)3]S 2O3, and Hg[Co(SCN)4]. The reaction was completed smoothly at room temperature and afforded corresponding mono-nitro derivatives in quantitative yield. This new method offers efficient and facile regioselective mononitration of aromatic compounds. Taylor & Francis Group, LLC.
Abdulla,Amina,Kumar, Y. Arun,Arifuddin,Rajanna
experimental part
p. 2946 - 2951
(2011/09/12)

Thermally decomposed Ni-Fe-hydrotalcite: A highly active catalyst for the solvent-free N-acylation of different amines by acid chlorides
A composite Ni-Fe catalyst obtained from the thermal decomposition of Ni-Fe-hydrotalcite at 600 °C shows very high activity in the solvent-free N-acylation of amines by different acid chlorides with high product yields under very mild reaction conditions (viz. room temperature, short reaction period and small amount of catalyst). The catalyst also shows excellent reusability in the reaction. The crystalline phases present in the catalyst are mixed oxides and hydroxides of nickel and iron. The high catalytic activity of the decomposed Ni-Fe-hydrotalcite is attributed to the formation of uniformly distributed Ni-Fe metal oxides and hydroxides.
Choudhary,Dumbre
experimental part
p. 1351 - 1356
(2012/01/06)

Synthesis of benzimidazoles by phosphine-mediated reductive cyclisation of ortho-nitro-anilides
Heating ortho-nitro-anilides 1-3 and 2-methyl-N-(3-nitropyridin-2-yl) propanamide (5) with 4 equiv. of a phosphine led to the 2-substituted benzimidazoles 6-8 and to the imidazo[4,5-b]pyridine 10, respectively, in yields between 45 and 85%. Heating 1 with (EtO)3P effected cyclisation and N-ethylation, leading to the 1-ethylbenzimidazole 6b. The slow cyclisation of the N-pivaloylnitroaniline 2b allowed isolation of the intermediate phosphine imide 11 that slowly transformed into the 1H-benzimidazole 7b. The structure of 11 was established by crystal-structure analysis. While the N-methylated ortho-nitroacetanilide 3 cyclised to the 1,2-dimethyl-1H-benzimidazole (8), the 2-methylpropananilide 4 was transformed into 1-methyl-3-(1-methylethyl)-2H- benzimidazol-2-one (9).
Duchek, Jan,Vasella, Andrea
experimental part
p. 977 - 986
(2011/08/05)

Beckmann rearrangement of oximes using pivaloyl chloride/DMF complex
A new complex of pivaloyl chloride and DMF was found to be very effective for converting ketoximes into their corresponding amides or lactams with excellent conversion via the Beckmann rearrangement. This method offers significant advantages such as efficiency and mild reaction conditions with shorter reaction time.
Narahari, Srinivasa Reddy,Reguri, Buchi Reddy,Mukkanti
experimental part
p. 4888 - 4891
(2011/10/05)

Synthesis, photophysical and NMR evaluations of thiourea-based anion receptors possessing an acetamide moiety
The synthesis and photophysical evaluation of three diaryl thiourea-based anion receptors (4-6) for comparison with their urea counterparts (1-3) is outlined. These anion receptors posses an acetamide functionality on one of the aryl groups and an electron-withdrawing CF3 group on the other. By varying the position of the acetamide group, in the o-, m- and p-positions of 4-6, respectively, the anion binding ability was both tuneable and found to be, in some cases, significantly different from that seen for the urea analogues 1-3. The binding affinities of the receptors 4-6, as well as the binding stoichiometries, were evaluated using UV-vis absorption spectroscopy in MeCN. However, these receptors were not sufficiently emissive to quantify the anion recognition using fluorescence. The results confirmed strong binding of these receptors to anions such as fluoride, acetate, phosphate, pyrophosphate and chloride. Nevertheless, the overall results obtained did not conform to the anticipated trends seen for 1-3, which is most likely due to the enhanced binding affinity of the thiourea analogues 4-6. The binding interactions were also investigated by using 1H NMR which confirmed that these receptors interacted with the anions in a stepwise manner, where the primary anion binding interaction occurred at the thiourea side, which led to an activation of the acetamide moiety towards the second anion binding interaction, an example of an allosteric activation mode.
Boyle, Elaine M.,McCabe, Thomas,Gunnlaugsson, Thorfinnur
experimental part
p. 586 - 597
(2011/01/03)

Microwave-assisted synthesis of nano-sized cadmium oxide as a new and highly efficient catalyst for solvent free acylation of amines and alcohols
In present studies, a new and efficient method for synthesis of cadmium oxide nanoparticles by using microwave (MW) activation is reported. To ensure the specific efficiency of microwave irradiation versus conventional heating, the synthesis of Cd(OH)2 as precursor of CdO was carried out under similar temperature (80 °C), time and reaction conditions without microwave irradiation. The formation of CdO was characterized by XRD, TEM, FT-IR analysis. Catalytic activity of CdO nanopowder for acylation of alcohols, phenols and amines has been investigated. The results show that the reaction times and yields of desired products were improved by using CdO.
Mazaheritehrani,Asghari,Orimi, R. Lotfi,Pahlavan
experimental part
p. 2554 - 2564
(2010/10/21)

Mild and useful method for n-acylation of amines
Iodine is found to promote quantitative N-acylation of primary and secondary amines (aliphatic and aromatic) in a very short time with an equimolar amount of acetyl chloride and benzoyl chloride under solvent-free conditions at room temperature. This catalytic acylation of amines offers an additional useful method for the acetylation using acetyl chloride instead of acetic anhydride and other acetylating agents. This method is also useful in the N-acylation of heterocycles. Mild reaction condition, high selectivity, efficiency, and good yields are some of the major advantages of the procedure.
Phukan, Kandarpa,Ganguly, Mausumi,Devi, Nirada
experimental part
p. 2694 - 2701
(2009/12/06)

Chemoselective acylation of amines, thiols and phenols using 2,4,6-triacyloxy-1,3,5-triazine (TAT) as a new and effective reagent under mild condition
A facile chemoselective acylation of amines, thiols and phenols using 2,4,6-triacyloxy-1,3,5-triazine (TAT) under mild condition is described. New reagent, high product yield, short reaction time, ease of operation and solvent free reaction condition is the most acceptable feature of the present method.
Gholap, Somnath S.,Tambe, Ganesh B.,Gill, Charansingh H.
experimental part
p. 179 - 182
(2010/04/05)

Silica supported zinc chloride catalyzed acetylation of amines, alcohols and phenols
Silica supported zinc chloride (SiO2-ZnCl2) has been prepared and found to efficiently catalyze the acetylation of amines, alcohols and phenols by stirring in acetonitrile at 80°C under heterogeneous conditions. The catalyst can be separated from the reaction medium simply by filtration and re-used up to four times.
Gupta, Raman,Kumar, Vineet,Gupta, Monika,Paul, Satya,Gupta, Rajive
experimental part
p. 1739 - 1743
(2009/06/28)

The recognition and sensing of anions through "positive allosteric effects" using simple urea-amide receptors
(Chemical Equation Presented) The design, synthesis, and X-ray crystallographic analysis of three simple diaryl-urea based anion receptors possessing an amide moiety on one of the aryl groups, and an electron withdrawing CF3 group on the other, is described. The three receptors differ only in the position of the amide functionality relative to the hydrogen bonding urea moiety (being para, meta, and ortho for 1, 2, and 3, respectively). This simple modification was shown to have a significant effect on the anion recognition ability, the strength of the recognition process, and the stoichiometry (host/guest) for these sensors. We demonstrate, by using both UV-vis absorption and 1H NMR spectroscopy, that these factors are caused by the ability of the amide moiety to both modulate the anion binding selectivity and the sensitivity of the urea moiety. We also demonstrate that, in the case of 1 and 2, this anion recognition at the urea moiety leads to concomitant activation (through enhanced inductive effect) in the amide functionality toward anions, which leads to the formation of an overall 1:2 (sensor/anion) binding stoichiometry for these receptors. This "activation" we describe as being an example of a "positive allosteric activation" by the urea site, caused directly by the first anion binding interaction, which to the best of our knowledge, has not been previously demonstrated for anion recognition and sensing.
Dos Santos, Cidalia M. G.,McCabe, Thomas,Watson, Graeme W.,Kruger, Paul E.,Gunnlaugsson, Thorfinnur
supporting information; experimental part
p. 9235 - 9244
(2009/04/06)

SO42-/SnO2: Efficient, chemoselective, and reusable catalyst for acylation of alcohols, phenols, and amines at room temperature
SO42-/SnO2 was employed for the acylation of a variety of alcohols, phenols, and amines under solvent-free conditions at room temperature. This method showed preferential selectivity for acetylation of the amino group in the presence of a hydroxyl group. The reported method is simple, mild, and environmentally viable, using several other acid anhydrides at room temperature. Copyright Taylor & Francis Group, LLC.
Satam, Jitendra R.,Gawande, Manoj B.,Deshpande, Sameer S.,Jayaram, Radha V.
p. 3011 - 3020
(2008/02/12)

Acetylation of some organic compounds under microwave irradiation
Acetic acid has been used for acetylation of seven aromatic amines and two phenols under microwave exposure. The time taken for these reactions ranges from 18-25 min with reasonability good yields (65-77%).
Jain, Deepika,Soni, Murli Dhar,Vardia, Jitendra,Punjabi,Ameta, Suresh C.
p. 188 - 188
(2008/03/11)

Nitration of aromatic compounds catalyzed by divanadium-substituted molybdophosphoric acid, H5[PMo10V2O 40]
The nitration of aromatic compounds was carried out in the presence of divanadium-substituted molybdophosphoric acid, H5PMo 10V2O40, as catalyst and a mixture of nitric acid and acetic anhydride as nitrating agent. In the presence of this heteropolyacid the ortho- and para-nitro compounds were obtained in good to excellent yields under mild reaction conditions. Springer-Verlag 2007.
Heravi, Majid M.,Bakhtiari, Khadijeh,Benmorad, Tina,Bamoharram, Fatemeh F.,Oskooie, Hossein A.,Tehrani, Maryam H.
p. 449 - 452
(2008/02/02)

Helical conformational dynamics and photoisomerism of alternating pyridinedicarboxamide/m-(phenylazo)azobenzene oligomers
Alternating sequences of pyridine-2,6-dicarboxamides and meta-(phenylazo)azobenzenes have been assembled into oligomers composed of four (8) and eight (9) azobenzene linkages. X-ray crystallography confirmed that oligomer 8 adopts a two-turn helical conformation with a helical pitch of approximately 3.4 A in the solid state. The presence of a two- and four-turn helical conformation of 8 and 9, respectively, in polar and nonpolar solvents was elucidated by the anisotropic upfield shifting of protons located within the helices, NOE enhancements between protons oriented toward the helix interior, and the diastereotopicity of the terminal benzyloxycarbonyl (CBz) methylene protons. 1H NMR line shape analysis of the CBz methylene hydrogens at the chain ends revealed a dynamic equilibria interconverting M and P helical conformations with energetic barriers (ΔG?) of 11.1 (ΔS? = -19.4 ± 1.6 cal mol-1 K-1; ΔH? = 6.5 ± 0.4 kcal/mol) for 8 and 13.8 kcal/mol (ΔS? = -6.6 ± 6.2 cal mol -1 K-1; ΔH? = 11.8 ± 1.8 kcal/mol) for 9. Irradiation of the oligomers with 350 nm light induces an E → Z isomerization of the azo linkages that decreases in efficacy at longer helix lengths. The suppression of E -Z isomerization is a consequence of the contrasting behavior of the azo linkages located at the helix termini, which afford ZIE ratios similar to those of model compound 7d, and the internal azo groups, which undergo significantly lower ZIEconversion ratios compared with 7e.
Tie, Chenyang,Gallucci, Judith C.,Parquette, Jon R.
p. 1162 - 1171
(2007/10/03)