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Cyanomethylation of the Benzene Rings and Pyridine Rings via Direct Oxidative Cross-Dehydrogenative Coupling with Acetonitrile
A novel and efficient approach for the amine-directed dehydrogenative C(sp2)-C(sp3) coupling of arylamines with acetonitrile was reported by using FeCl2as the catalyst. Substituted anilines, aminopyridines, naphthylamines, and some nitrogen-containing heterocyclic arylamines react with inactive acetonitrile to form the corresponding arylacetonitriles in moderate to good yields. This protocol features nontoxic iron catalysis, efficient atom economy, nonprefunctionalized starting materials, good regioselectivity, and excellent compatibility of functional groups and aromatic rings, providing a novel, straightforward, and green approach toward arylacetonitriles.
Lin, Sen,Wang, Bingqing,Yan, Zhaohua,Yao, Hua,Zhong, Xiaoyang
supporting information
p. 2030 - 2034
(2022/03/31)

A mild and selective Cu(II) salts-catalyzed reduction of nitro, azo, azoxy, N-aryl hydroxylamine, nitroso, acid halide, ester, and azide compounds using hydrogen surrogacy of sodium borohydride
The first mild, in situ, single-pot, high-yielding well-screened copper (II) salt-based catalyst system utilizing the hydrogen surrogacy of sodium borohydride for selective hydrogenation of a broad range of nitro substrates into the corresponding amine under habitancy of water or methanol like green solvents have been described. Moreover, this catalytic system can also activate various functional groups for hydride reduction within prompted time, with low catalyst-loading, without any requirement of high pressure or molecular hydrogen supply. Notably, this system explores a great potential to substitute expensive traditional hydrogenation methodologies and thus offers a greener and simple hydrogenative strategy in the field of organic synthesis.
Kalola, Anirudhdha G.,Prasad, Pratibha,Mokariya, Jaydeep A.,Patel, Manish P.
supporting information
p. 3565 - 3589
(2021/10/12)

Monolithic Silica Support for Immobilized Catalysis in Continuous Flow
Monolithic and packed-bed reactors featuring immobilized catalysts are well-precedented in continuous flow synthesis but can suffer from adverse pressure drops during use due to their small pore sizes and/or structural changes. Herein, we overcome this challenge with the synthesis of a structurally robust silica-based monolith featuring pore sizes on the millimeter scale. The 3-dimensional solid support structure is constructed from a polystyrene foam-based template and features a functional group handle that can be modified to display a reactive catalyst. Here we functionalize the support with palladium(0) for hydrogenation reactions and a modified proline catalyst for the alpha functionalization of aldehydes. Both reactors showed good activity and excellent catalytic longevity when utilized under continuous flow conditions. (Figure presented.).
Russell, M. Grace,Veryser, Cedrick,Hunter, James F.,Beingessner, Rachel L.,Jamison, Timothy F.
supporting information
p. 314 - 319
(2019/12/24)

Ultrasound-assisted rapid reduction of nitroaromatics to anilines using gallium metal
The reduction of nitroaromatic compounds to anilines is widely used throughout organic synthesis. Typical methods of performing this transformation utilize hydrogenation over a pyrophoric catalyst or a finely divided reducing metal, which often affords heterogeneous mixtures that are difficult to purify. Herein, we report for the first time the use of gallium metal as a reducing agent in organic synthesis. The reaction proceeds under aerobic conditions and affords homogeneous mixtures for a convenient workup. Using this method, twelve anilines were obtained in 33% to quantitative yields with short reaction times of 10-60 minutes.
Bento, Ian,Bernaldez, Mabel,Noguchi, Ryden,Kawakami, Joel
supporting information
p. 1404 - 1407
(2020/03/31)

Simple reversible fixation of a magnetic catalyst in a continuous flow system: Ultrafast reduction of nitroarenes and subsequent reductive amination using ammonia borane
Continuous reductive amination of aldehydes with nitroarenes over a Pd-Pt-Fe3O4 catalyst was performed. We used NH3BH3 as not only a hydrogen source for nitro reduction, but also a reductant for imine reduction. Secondary aromatic amines were obtained in the continuous flow reaction in good to excellent yields.
Byun, Sangmoon,Cho, Ahra,Kang, Dong Yun,Kim, B. Moon,Kim, Ha Joon,Kim, Hong Won,Kim, Seong Min,Lei, Cao,Park, Jin Kyoon
p. 944 - 949
(2020/03/11)

Preparation method of arylamine compound
The invention belongs to the technical field of natural compounds, pharmaceutical and chemical intermediates and related chemistry, and provides a preparation method of arylamine compounds. The methoduses aromatic nitro compounds as raw materials, a nano porous platinum-iron catalyst as a catalyst and hydrogen as a hydrogen source to prepare arylamine through selective hydrogenation. The adoptedcatalyst is the nano porous platinum-iron catalyst, the pore size is 1nm-50nm, and the molar ratio of the aromatic nitro compound to the catalyst is 1:0.01-1:0.5; the pressure of the hydrogen is 0.1-20.0 MPa; and the molar concentration of the nitro compound in the solvent is 0.01-2 mmol/mL. The method has the beneficial effects that the reaction conditions are very mild, the product selectivity is high, the operation and post-treatment are simple, the catalyst activity is high, the property is stable, the price is low, the reproducibility is good, the catalytic effect is not obviously reducedafter repeated use for multiple times, and the possibility is provided for industrialization.
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Paragraph 0036-0043

(2020/12/10)

Hydrogenation of nitroarenes to anilines in a flow reactor using polystyrene supported rhodium in a catalyst-cartridge (Cart-Rh@PS)
The present methodology described the chemo-selective hydrogenation of various nitroarenes in a flow reactor under polystyrene supported rhodium in a catalyst-cartridge (Cart-Rh@PS) as a heterogeneous nano-catalyst. The polystyrene supported Rh (Rh@PS) nanoparticles (NPs) were prepared by following our earlier reported protocol and packed inside the catalyst-cartridge (Cat-Cart) to obtain Cart-Rh@PS, which is compatible with ThalesNano's H-Cube Pro flow system. The advantages of the prepacked catalyst Cart-Rh@PS are as follows: no need for catalyst activation up to 12 runs, negligible metal leaching detected by ICP-AES analysis and significantly less back pressure generated under the flow conditions. The same catalyst, Cart-Rh@PS, was also effective up to a 1 gram scale for the reduction of nitroarenes and reusable for successive runs. The hydrogenation in the flow reactor is a greener approach for the reduction of nitroarenes to their corresponding anilines in high yields.
Sharma, Saurabh,Yamini,Das, Pralay
supporting information
p. 1764 - 1769
(2019/01/28)

Hydrogenation of nitroarenes catalyzed by a dipalladium complex
A dipalladium complex [Pd2(L)Cl2](PF6)2 (2), via the substitution of (PhCN)2PdCl2 with 5-phenyl-2,8-bis(6′-bipyridinyl)-1,9,10-anthyridine (L) followed by the anion exchange, was found to be a good pre-catalyst for the reduction of nitroarenes to yield the corresponding anilines under atmospheric pressure of hydrogen in methanol. This method provides a straightforward access to a diverse array of functionalized anilines, exhibiting a possible application in synthetic chemistry. The catalytic activity of this complex is enhanced by the di-metallic system via the synergistic effect.
Hung, Ming-Uei,Yang, Shu-Ting,Ramanathan, Mani,Liu, Shiuh-Tzung
(2017/09/06)

Preparation method of apatinib
The invention discloses a preparation method of apatinib and belongs to the field of medicine and fine chemical industry. The preparation method is a novel preparation scheme; a target compound that is satisfactory can be acquired with any intermediate. The preparation method has the advantages the advantages of short procedure, simple reacting steps, good safety and reliability, high yield, low cost, high purity, low pollution, good operational simplicity and the like.
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Paragraph 0083; 0091; 0092; 0093; 0094

(2018/09/11)

Preparation of Well-Ordered Mesoporous-Silica-Supported Ruthenium Nanoparticles for Highly Selective Reduction of Functionalized Nitroarenes through Transfer Hydrogenation
MCM-41-type mesoporous silica (OMS-IL) was prepared by using an ionic liquid (1-hexadecyl-3-methylimidazolium bromide) as a template. The XRD and TEM results demonstrated that OMS-IL was more stable than the MCM-41 material. Ru nanoparticles were supported on OMS-IL (Ru/OMS-IL) by impregnating OMS-IL with a RuCl3 aqueous solution, and the resulting material was used for the selective reduction of nitroarenes. The effects of the components of the catalysts and the reaction conditions on the catalytic behavior of the prepared catalysts were investigated in detail. Ru/OMS-IL exhibited high catalytic activity and chemoselectivity for the reduction of various substituted nitroarenes to the corresponding aromatic amines in ethanol with hydrazine hydrate as a hydrogen donor under mild conditions. The Ru/OMS-IL catalysts were highly stable and could easily be recovered by simple filtration over at least six recycling reactions without any observable loss in catalytic performance.
Wei, Ning,Zou, Xiujing,Huang, Haigen,Wang, Xueguang,Ding, Weizhong,Lu, Xionggang
supporting information
p. 209 - 214
(2018/01/26)

Nitrogen-doped graphene-activated metallic nanoparticle-incorporated ordered mesoporous carbon nanocomposites for the hydrogenation of nitroarenes
Herein, nanoscale metallic nanoparticle-incorporated ordered mesoporous carbon catalysts activated by nitrogen-doped graphene (NGr) were fabricated via an efficient multi-component co-assembly of a phenolic resin, nitrate, acetylacetone, the nitrogen-containing compound 1,10-phenanthroline, and Pluronic F127, followed by carbonization. The obtained well-dispersed nitrogen-doped graphene-activated transition metal nanocatalysts possess a 2-D hexagonally arranged pore structure with a high surface area (～500 m2 g-1) and uniform pore size (～4.0 nm) and show excellent activity for the selective hydrogenation-reduction of substituted nitroarenes to anilines in an environmentally friendly aqueous solution. The high catalytic performance and durability is attributed to the synergistic effects among the components, the unique structure of the nitrogen-doped graphene layer-coated metallic nanoparticles, and electronic activation of the doped nitrogen.
Huang, Haigen,Wang, Xueguang,Sheng, Yao,Chen, Chenju,Zou, Xiujing,Shang, Xingfu,Lu, Xionggang
p. 8898 - 8909
(2018/03/08)

Nitrogen-Doped Graphene-Supported Iron Catalyst for Highly Chemoselective Hydrogenation of Nitroarenes
A nitrogen-doped graphene-supported iron catalyst was used for the first time in the hydrogenation of a series of nitroarenes to give the corresponding amines with excellent activity and chemoselectivity under mild reaction conditions. Physicochemical characterization of the catalyst by transmission electron microscopy, X-ray diffraction, X-ray photoelectron spectroscopy, and M?ssbauer spectroscopy revealed the formation of iron particles with an iron oxide core and a metallic iron shell that were coated by a few layers of nitrogen-doped graphene. The unique structure of FeNx/C in the catalyst was proven to contribute to the hydrogenation activity.
Wei, Zuojun,Hou, Yaxin,Zhu, Xinmiao,Guo, Liangyu,Liu, Yingxin,Zhang, Anyun
p. 2009 - 2013
(2018/03/21)

N-doped graphitic carbon-improved Co-MoO3 catalysts on ordered mesoporous SBA-15 for chemoselective reduction of nitroarenes
Metallic Co-MoO3 catalysts supported on ordered mesoporous SBA-15 were first prepared through in situ reaction of SBA-15-supported Co-Mo oxides with 1,10-phenanthroline. The resulting Co-MoO3/NC@SBA-15 catalysts with N-doped carbon (NC) exhibited high catalytic activity and chemoselectivity for selective reduction of various functionalized nitroarenes to the corresponding arylamines in ethanol with hydrazine hydrate at near room temperature (30 °C). For reduction of all tested substrates (28 examples), the catalyst could afford a conversion of >99% and arylamine selectivity of >99%. The excellent catalytic performance of the Co-MoO3/NC@SBA-15 was attributed to the Co-Nχ(C)-Mo active sites generated through the interaction between the surface Co-Nχ(C) and MoO3 species, promoting the dissociation of hydrazine molecule into the active H* species for the reduction of nitro groups. After the seventh cycle for reduction of 4-methoxylnitrobenzene, the 2%Co-MoO3/NC@SBA-15 showed little change in catalytic performance, textural properties, size and dispersion of metal species and valence states of elements, indicating high stability and recyclability.
Huang, Haigen,Liang, Xiangcheng,Wang, Xueguang,Sheng, Yao,Chen, Chenju,Zou, Xiujing,Lu, Xionggang
p. 127 - 137
(2018/05/04)

Catalytic Reduction of Nitroarenes by Dipalladium Complexes: Synergistic Effect
The direct reaction between 2,7-bis(2-pyridinyl)-1,8-naphthyridine (bpnp) and Pd(CH3COO)2 in CF3COOH yields the new dinuclear palladium(II) complex [Pd2(bpnp)(μ-OH)(CF3CO2)2](CF3CO2) (1). Similarly, substitution of Pd(CH3CN)4(BF4)2 with bpnp in DMF gives [Pd2(bpnp)(μ-OH)(DMF)2](BF4)3 (2). Treatment of 1 or 2 with Cl- readily provide the chloro-substituted species [Pd(bpnp)(μ-OH)(Cl)2]+. All complexes were characterized by spectroscopic methods, and the structure of 2 was further confirmed by X-ray crystallography. Complex 1 is an efficient catalyst for the reduction of aromatic nitro compounds leading to the corresponding aniline derivatives under atmospheric pressure of hydrogen at 50 °C. The mechanistic pathway of the catalysis is investigated. From the reaction pathway, it is suggested that a facile condensation of nitroso and hydroxylamine intermediates is enabled by the dipalladium system and the desired transformation proceeds smoothly under mild reaction conditions to yield the reduced product.
Yang, Shu-Ting,Shen, Peng,Liao, Bei-Sih,Liu, Yi-Hung,Peng, Shie-Ming,Liu, Shiuh-Tzung
supporting information
p. 3110 - 3116
(2017/09/05)

Highly chemoselective reduction of nitroarenes over non-noble metal nickel-molybdenum oxide catalysts
The chemoselective reduction of nitroarenes is an important transformation for the production of arylamines, which are the primary intermediates in the synthesis of pharmaceuticals, agrochemicals and dyes. Heterogeneous non-noble metal nickel-molybdenum oxide catalysts supported on ordered mesoporous silica SBA-15 (Ni-MoO3/CN@SBA-15) were prepared for the first time by treating SBA-15-supported nickel-molybdenum oxide materials with 1,10-phenanthroline, and exhibited unprecedented catalytic activity and chemoselectivity for the reduction of various substituted nitroarenes to the corresponding aromatic amines in ethanol with hydrazine hydrate as a hydrogen donor under mild conditions owing to the synergistic effect of metal Ni and MoO3 species, affording excellent yields of >99% within very short reaction periods (≤60 min). The Ni-MoO3/CN@SBA-15 catalysts were highly stable and could easily be recovered by simple filtration or by an external magnetic field for at least ten recycling reactions without any observable loss of catalytic performance or leaching of metal components.
Huang, Haigen,Wang, Xueguang,Li, Xu,Chen, Chenju,Zou, Xiujing,Ding, Weizhong,Lu, Xionggang
p. 809 - 815
(2017/08/15)

Study on a New Method for Synthesis of Mirabegron
Mirabegron is a muscle relaxing drug for the treatment of overactive bladder. The existing synthetic methods for mirabegron produced intermediate product 4-(2-(phenethylamino)ethyl)aniline, which complicated the final product purification process. In this study, we designed a new synthetic route for mirabegron with low cost starting materials and a production of mirabegron at a 99.6% purity and a 61% overall yield. Particularly, this new synthetic route did not produce side product 4-(2-(phenethylamino)ethyl)aniline, which significantly simplified the product purification process.
Xu, Guiqing,Mao, Shen,Mao, Longfei,Jiang, Yuqin,Zhou, Yong,Shen, Jiaxuan,Dong, Wenpei
p. 2703 - 2707
(2017/09/26)

High Performance and Active Sites of a Ceria-Supported Palladium Catalyst for Solvent-Free Chemoselective Hydrogenation of Nitroarenes
Cerium oxide-supported palladium catalysts (Pd/CeO2) prepared by a simple impregnation method exhibit exciting catalytic activity and high chemoselectivity for the solvent-free hydrogenation of a variety of substituted nitroarenes including the reducible functional groups to the corresponding aromatic amines under mild reaction conditions. Taking nitrobenzene as an example, the Pd/CeO2 catalyst can afford aniline yields of >99 % with turnover frequencies as high as 11 411 h?1 and 69 824 h?1 at 40 °C and 100 °C, respectively. Pd2+ ion species exist as isolated single atoms with ?Pd2+?O2??Ce4+? linkages on the surface of PdxCe1?xO2?σ solid solution and are found to be active sites for the selective hydrogenation of nitroarenes in the absence of solvent. The superior catalytic performance can be attributed to the cooperative effect between Pd2+ ions and unique surface sites of CeO2. A possible mechanism is proposed for the hydrogenation of nitroarenes with H2 over the Pd/CeO2. The Pd/CeO2 catalyst can be recovered easily and reused for at least seven recycling reactions without loss of catalytic properties.
Shi, Xiuxiu,Wang, Xueguang,Shang, Xingfu,Zou, Xiujing,Ding, Weizhong,Lu, Xionggang
p. 3743 - 3751
(2017/10/16)

Benzyltin pyrimidine derivatives, their preparation and their use as medicaments
The invention relates to the field of pharmaceutical chemistry, specifically to benzyl pyrimidine derivatives (I), preparation methods thereof, medicinal compositions containing the derivatives and medical application of the derivatives, in particular, application of the derivatives as an immunosuppressant in autoimmune diseases and organ transplantation.
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(2017/01/19)

Solvent-Free Selective Hydrogenation of Nitroarenes Using Nanoclusters of Palladium Supported on Nitrogen-Doped Ordered Mesoporous Carbon
The selective hydrogenation of nitroarenes is a key transformation for the production of aromatic amines, which are primary intermediates in the synthesis of pharmaceuticals, agrochemicals, and dyes. However, most reaction processes require toxic organic solvents and suffer from poor selectivity in the presence of other reducible groups. Herein, we report a successful example of nanoclusters of ultrafine Pd supported on N-modified ordered mesoporous CMK-3 carbon (Pd/N-CMK-3) prepared by a facile two-step impregnation route with aqueous solutions of 1,10-phenanthroline and H2PdCl4 that hydrogenated various nitroarenes highly efficiently and selectively to the corresponding aromatic amines with hydrogen in the absence of solvent. The Pd/N-CMK-3 catalyst could be recovered easily for multiple recycling reactions without a loss of catalytic performance.
Huang, Haigen,Wang, Xueguang,Tan, Mingwu,Chen, Chenju,Zou, Xiujing,Ding, Weizhong,Lu, Xionggang
p. 1485 - 1489
(2016/05/02)

NOVEL PROCESS FOR PREPARATION OF MIRABEGRON AND IT'S INTERMEDIATE
The present invention related to a novel process for preparation of Mirabegron of formula (I) and its intermediate. I
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(2015/11/10)

Indium(III)-Catalyzed Reduction of Nitrobenzenes to Anilines: Scope and Limitations
We have demonstrated that a combination of indium(III) iodide and 1,1,3,3-tetramethyldisiloxane (TMDS) effectively catalyzes the chemoselective reduction of nitrobenzenes with a variety of functional groups (halogens, alkyl, alkoxy, hydroxy, ester, amino, amide, cyanide, thiol, and an alkene moiety), producing the corresponding aniline derivatives.
Sakai, Norio,Asama, Shun,Konakahara, Takeo,Ogiwara, Yohei
p. 3179 - 3185
(2015/10/19)

Highly efficient and selective photocatalytic reduction of nitroarenes using the Ni2P/CdS catalyst under visible-light irradiation
A highly efficient and selective heterogeneous photocatalytic system for nitro reduction to amino organics was established using CdS, Ni2P and Na2S/Na2SO3 as a photosensitizer, a cocatalyst and a sacrificial electron donor in aqueous solution, respectively. Two competing pathways for photocatalytic H2 production and nitro reduction were found. Also, the reduction of nitroarenes to aniline was confirmed to proceed through both the direct and condensation routes.
Gao, Wen-Zheng,Xu, Yong,Chen, Yong,Fu, Wen-Fu
p. 13217 - 13220
(2015/08/18)

Transfer hydrogenation of nitroarenes into anilines by palladium nanoparticles via dehydrogenation of dimethylamine borane complex
This work reports a simple and highly efficient protocol for reduction of nitroarenes to corresponding amines via dehydrogenation of dimethylamine borane using palladium nanoparticle (Pd NPs) as a versatile heterogeneous catalyst. The facile approach for the synthesis of Pd NPs within 15 min in aqueous medium has been reported. The Pd NPs were well characterized using various analytical techniques such as XRD, FEG-SEM, TEM, EDAX and XPS. The developed catalytic system uses environmentally benign dimethylamine borane as a reducing agent which is highly stable, water soluble and nontoxic. The various amines were synthesized from nitroarenes in excellent yields within 10-60 min at room temperature. The catalyst was reused up to four successive cycles without significant loss in its catalytic activity.
Patil, Nilesh M.,Bhosale, Manohar A.,Bhanage, Bhalchandra M.
p. 86529 - 86535
(2015/11/03)

Efficient palladium-catalyzed C-O hydrogenolysis of benzylic alcohols and aromatic ketones with polymethylhydrosiloxane
A simple method has been developed for the reductive deoxygenation of aromatic ketones and benzylic alcohols in the presence of polymethylhydrosiloxane (PMHS). The reductive deoxygenation of aromatic ketones and benzylic alcohols, including secondary alcohols, to the corresponding methylene hydrocarbons has been achieved in good to excellent yields using palladium chloride (PdCl2) as catalyst and PMHS as hydride source. Such deoxygenations were successfully with aryl alkyl ketones and diaryl ketones, as exemplified by the reductive deoxygenation of acetophenone and benzopheneone, respectively. The corresponding benzylic alcohols and secondary alcohol analogues could also be converted into their respective methylene hydrocarbons by the PdCl2/PMHS system.
Wang, Hu,Li, Li,Bai, Xing-Feng,Shang, Jun-Yan,Yang, Ke-Fang,Xu, Li-Wen
supporting information
p. 341 - 347
(2013/05/08)

Enhancement of kinase selectivity in a potent class of arylamide FMS inhibitors
Structure-activity relationship (SAR) studies on a highly potent series of arylamide FMS inhibitors were carried out with the aim of improving FMS kinase selectivity, particularly over KIT. Potent compound 17r (FMS IC50 0.7 nM, FMS cell IC50 6.1 nM) was discovered that had good PK properties and a greater than fivefold improvement in selectivity for FMS over KIT kinase in a cellular assay relative to the previously reported clinical candidate 4. This improved selectivity was manifested in vivo by no observed decrease in circulating reticulocytes, a measure of bone safety, at the highest studied dose. Compound 17r was highly active in a mouse pharmacodynamic model and demonstrated disease-modifying effects in a dose-dependent manner in a strep cell wall-induced arthritis model of rheumatoid arthritis in rats.
Illig, Carl R.,Manthey, Carl L.,Meegalla, Sanath K.,Wall, Mark J.,Chen, Jinsheng,Wilson, Kenneth J.,Desjarlais, Renee L.,Ballentine, Shelley K.,Schubert, Carsten,Crysler, Carl S.,Chen, Yanmin,Molloy, Christopher J.,Chaikin, Margery A.,Donatelli, Robert R.,Yurkow, Edward,Zhou, Zhao,Player, Mark R.,Tomczuk, Bruce E.
p. 6363 - 6369
(2013/11/19)

Pinacol as a new green reducing agent: Molybdenum-catalyzed chemoselective reduction of sulfoxides and nitroaromatics
Pinacol is disclosed as a new chemoselective and environmentally benign reducing agent for sulfoxides and nitroaromatics assisted by readily available dichlorodioxomolybdenum(VI) complexes as catalysts. A wide range of substrates including those bearing challenging functional groups has been efficiently and selectively reduced with acetone and water being the only by-products of these reactions. Copyright
Garcia, Nuria,Garcia-Garcia, Patricia,Fernandez-Rodriguez, Manuel A.,Rubio, Ruben,Pedrosa, Maria R.,Arnaiz, Francisco J.,Sanz, Roberto
supporting information; experimental part
p. 321 - 327
(2012/04/11)

Mixed lanthanide succinate-sulfate 3D MOFs: Catalysts in nitroaromatic reduction reactions and emitting materials
The first series of mixed succinate/sulfate/Ln MOFs, [Ln2(C 2H4C2O4)2(SO 4)(H2O)2] (RPF-16), where Ln = La, Pr, Nd, and Sm, were hydrothermally obtained and their structures determined by X-ray single crystal diffraction. The crystalline products are a series of isostructural 3D polymeric compounds that crystallise in the monoclinic space group P2(1)/n. Their framework comprises infinite crossing chains of LnO9 sharing edges polyhedra, kept together by succinate and sulfate anions. Topological simplification gives rise to a 3D uninodal six connected net of type pcu alpha-Po primitive cubic. These well-defined compounds show high chemoselectivity towards reduction of the nitro group and present bifunctional activity for the one-pot reductive amination of heptanal at near-complete conversion of the substrates. A general overview of the room-temperature luminescence behavior in the new RPF-16 Ln materials is also reported. The Royal Society of Chemistry 2011.
D'Vries, Richard F.,Iglesias, Marta,Snejko, Natalia,Alvarez-Garcia, Susana,Gutierrez-Puebla, Enrique,Monge, M. Angeles
experimental part
p. 1191 - 1198
(2012/04/04)

Palladium-catalyzed cyanomethylation of aryl halides through domino Suzuki coupling-isoxazole fragmentation
A one-pot protocol for the cyanomethylation of aryl halides through a palladium-catalyzed reaction with isoxazole-4-boronic acid pinacol ester was developed. Mechanistically, the reaction proceeds through (1) Suzuki coupling, (2) base-induced fragmentation, and (3) deformylation as shown by characterization of all postulated intermediates. Under optimized conditions (PdCl2dppf, KF, DMSO/H2O, 130 °C) a broad spectrum of aryl bromides could be converted into arylacetonitriles with up to 88% yield.
Velcicky, Juraj,Soicke, Arne,Steiner, Roland,Schmalz, Hans-Guenther
supporting information; experimental part
p. 6948 - 6951
(2011/06/19)

Selective reduction of nitro compounds using CeY zeolite under microwaves
Aliphatic and aromatic nitro compounds were selectively reduced to their corresponding amino derivatives in good yields using formic acid and CeY zeolite under monomode reactor. This system is found to be compatible with several sensitive functionalities. Beside the recycling result showed it had a long catalyst lifetime and could maintain activity even after being used for 20 cycles.
Arya, Kapil,Dandia, Anshu
experimental part
p. 55 - 58
(2010/09/05)

Efficient reducing system based on iron for conversion of nitroarenes to anilines
Reduction of nitroarenes with low solubility in EtOH-H2O to anilines easily occurs in a Fe-NH4Cl-acetone-H2O system, and treatment of the same nitroarenes with Fe-NH4Cl-EtOH-H2O hardly furnished the corresponding products. Under the reaction condition, the reducible or hydrolysable groups are not affected.
Xiao, Zhu-Ping,Wang, Ying-Chun,Du, Gao-Yu,Wu, Jun,Luo, Tao,Yi, Shou-Fu
experimental part
p. 661 - 665
(2011/03/19)

Synthesis, analgesic and anti-inflammatory activities of novel 3-(4-acetamido-benzyl)-5-substituted-1,2,4-oxadiazoles
A series of 3-(4-acetamido-benzyl)-5-substituted-1,2,4-oxadiazoles (7a-7n) were synthesized and screened for analgesic and in vivo anti-inflammatory activities using acetic acid writhing in mice model and carrageenan-induced paw oedema method in mice, respectively. The analgesic activity of compounds 7i and 7m is superior while that of 7d, 7c, 7f and 7j is equal to the reference standard, diclofenac sodium. The anti-inflammatory activity of compounds 6, 7c, 7e, 7f, 7i, 7l, 7m and 7n is found to be superior than that of diclofenac sodium which is used as a reference, while compounds 7d and 7g are found to be equipotent with the reference compound.
Farooqui, Mazahar,Bora, Rajesh,Patil
scheme or table
p. 794 - 799
(2009/09/08)

Synthesis of 3,5-disubstituted [1,2,4]-oxadiazoles
Substituted amidoximes have been synthesized, and converted to corresponding oxadiazoles as a novel heterocyclic compounds under mild conditions in good to excellent yield.
Bora, Rajesh O.,Farooqui, Mazahar
experimental part
p. 569 - 573
(2009/07/18)

Synthesis of substituted 1,2,4-oxadiazoles from substituted acid chlorides and amidoximes under mild conditions
(Chemical Equation Presented) Substituted amidoximes have been synthesized, isolated and converted into substituted oxadiazoles as a novel heterocyclic compounds under mild conditions in good to excellent yield.
Bora, Rajesh O.,Farooqui, Mazahar
p. 645 - 649
(2008/09/17)

Polymer-supported formate and zinc: A novel system for the transfer hydrogenation of aromatic nitro compounds
A mild and efficient catalytic transfer hydrogenation (CTH) system has been developed for the facile reduction of aromatic nitro compounds using recyclable polymer-supported formate in the presence of commercial zinc dust at room temperature. This method is found to give the product amine in excellent yield (92-98%) without the need for any chromatographic purification steps. Many other sensitive functional groups such as halogen, alkene, nitrile, carbonyl, ester and amide are compatible with the present system.
Srinivasa,Abiraj,Gowda, D. Channe
p. 297 - 301
(2007/10/03)

Facile water mediated chemo-selective synthesis of anilines from nitroarenes using triethylammonium formate
A simple and efficient protocol for the chemo-selective reduction of substituted nitroarenes to corresponding anilines in good yields using inexpensive commercial zinc dust and triethylammonium formate in water at ambient temperature and pressure is established. Many other reducible functional groups like methoxy, methyl, ester, nitrile, amide, acid, phenol and halogens are unaltered with the present systems.
Sridhara,Srinivasa,Gowda, D. Channe
p. 1304 - 1307
(2007/10/03)

Analysis of structure-activity relationships for the 'A-region' of N-(4-t-butylbenzyl)-N′-[4-(methylsulfonylamino)benzyl]thiourea analogues as TRPV1 antagonists
The structure-activity relationships for the 'A-region' of N-(4-t-butylbenzyl)-N′-[4-(methylsulfonylamino)benzyl]thiourea analogues have been investigated as TRPV1 receptor antagonists. The 2-halogen analogues showed enhanced antagonism compared to the prototype antagonist.
Lee, Jeewoo,Kang, Sang-Uk,Kil, Min-Jung,Shin, Myoungyoup,Lim, Ju-Ok,Choi, Hyun-Kyung,Jin, Mi-Kyoung,Kim, Su Yeon,Kim, Sung-Eun,Lee, Yong-Sil,Min, Kyung-Hoon,Kim, Young-Ho,Ha, Hee-Jin,Tran, Richard,Welter, Jacqueline D.,Wang, Yun,Szabo, Tamas,Pearce, Larry V.,Lundberg, Daniel J.,Toth, Attila,Pavlyukovets, Vladimir A.,Morgan, Matthew A.,Blumberg, Peter M.
p. 4136 - 4142
(2007/10/03)

Transfer hydrogenation of aromatic nitro compounds using polymer-supported formate and Pd-C
Transfer hydrogenation of aromatic nitro compounds using recyclable polymer-supported formate as hydrogen donor and Pd-C as a catalyst produces corresponding amines in excellent yields (90-98%).
Abiraj,Srinivasa,Gowda, D. Channe
p. 223 - 230
(2007/10/03)

Simple and efficient reduction of aromatic nitro compounds using recyclable polymer-supported formate and magnesium
Aromatic nitro compounds were chemoselectively reduced to the corresponding amines using recyclable polymer-supported formate as a hydrogen donor in the presence of low-cost magnesium powder at room temperature. Use of the immobilized hydrogen donor affords the product amine in excellent yield (90-97%) without the need for any Chromatographic purification steps. This method was found to be highly facile with selectivity over several other functional groups, such as halogen, alkene, nitrile, carbonyl, ester, amide, methoxy, phenol, and hydroxyl groups. CSIRO 2005.
Abiraj, Keelara,Srinivasa, Gejjalagere R.,Gowda, D. Channe
p. 149 - 151
(2007/10/03)

SELECTIVE HYDROGENATION OF NITROGEN CONTAINING AROMATICS
The present invention describes an improved catalyst and process for the selective hydrogenation of nitro aromatics, nitrosoaromatics and aromatic hydroxyl amines to their corresponding amines using gaseous hydrogen, in the presence of soluble iron compounds as a catalyst and optionally other reducible groups.
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Page/Page column 8

(2008/06/13)

A practical and chemoselective reduction of nitroarenes to anilines using activated iron
Reduction of nitroarenes to anilines using activated iron generated by Fe/HCl or Zn/FeSO4 is described. A variety of functional groups such as alkyne, ketone, enone, nitrile, lactone, and aromatic halide are well tolerated under these conditions.
Liu, Yugang,Lu, Yansong,Prashad, Mahavir,Repic, Oljan,Blacklock, Thomas J.
p. 217 - 219
(2007/10/03)

Polymer-supported formate and magnesium: An efficient transfer hydrogenation system for the facile reduction of azo compounds
A mild and efficient method was developed for the chemo-selective reduction of azo compounds to the corresponding amine/s using recyclable polymer-supported formate as hydrogen donor in the presence of low cost magnesium powder at room temperature.
Srinivasa,Abiraj,Gowda, D. Channe
p. 123 - 125
(2007/10/03)

Clean and efficient hydrogenative cleavage of azo compounds using polymer-supported formate and zinc
Azo compounds, both symmetric and asymmetric, were chemoselectively reduced to the corresponding amine(s) using recyclable polymer-supported formate as a hydrogen donor in the presence of zinc at room temperature. Copyright Taylor & Francis, Inc.
Srinivasa,Abiraj,Channe Gowda
p. 1161 - 1165
(2007/10/03)

Palladium-catalyzed simple and efficient hydrogenative cleavage of azo compounds using recyclable polymer-supported formate
Palladium-catalyzed room temperature transfer hydrogenation of azo compounds using recyclable polymer-supported formate as the hydrogen donor produces corresponding amine(s) in excellent yields (88%-98%). This method was found to be highly facile with selectivity over a number of other functional groups such as halogen, alkene, nitrile, carbonyl, amide, methoxy, and hydroxyl.
Abiraj, Keelara,Srinivasa, Gejjalagere R.,Gowda, D. Channe
p. 517 - 520
(2007/10/03)

Chemoselective hydrogenation of substituted nitroaromatics using novel water-soluble iron complex catalysts
Chemoselective hydrogenation of substituted nitroaromatic compounds by water-soluble iron complex catalysts with molecular hydrogen has been reported for the first time. This biphasic catalyst presents an opportunity for a solvent-free hydrogenation. This catalyst system provides a low-cost, efficient alternative to the selective but environmentally unacceptable stoichiometric reductions as well as the supported noble metal catalysts used for hydrogenation. An efficient recycling strategy has resulted in a cumulative turnover number above 6000.
Deshpande, Raj. M.,Mahajan, Avinash. N.,Diwakar, Makarand. M.,Ozarde, Prakash. S.,Chaudhari
p. 4835 - 4838
(2007/10/03)

Selective reduction of alkenes, α,β-unsaturated carbonyl compounds, nitroarenes, nitroso compounds, N,N-hydrogenolysis of azo and hydrazo functions as well as simultaneous hydrodehalogenation and reduction of substituted aryl halides over PdMCM-41 catalyst under transfer hydrogen conditions
Chemoselective reductions of alkenes, α,β-unsaturated carbonyl compounds, nitro and nitroso compounds, N,N-hydrogenolysis of azo and hydrazo functions as well as simultaneous reduction and hydrodehalogenation of substituted aryl halides, including bulkier substrates, were achieved by catalytic transfer hydrogenation (CTH) using mesoporous PdMCM-41 catalyst. The yields were practically unaffected upon recycling of the catalyst. Further, the CTH process is accomplished without affecting the reduction of any other reducible functional group.
Selvam, Parasuraman,Sonavane, Sachin U.,Mohapatra, Susanta K.,Jayaram, Radha V.
p. 3071 - 3075
(2007/10/03)

Analysis of structure-activity relationships with the N-(3-acyloxy-2- benzylpropyl)-N′-[4-(methylsulfonylamino)benzyl]thiourea template for vanilloid receptor 1 antagonism
In a continuing effort to elucidate the structure-activity relationships of the lead antagonist N-[2-(3,4-dimethylbenzyl)-3-pivaloyloxypropyl]-N ′-[4-(methylsulfonylamino)benzyl]thiourea (1), the distances between the proposed four pharmacophores in 1 have been varied by insertion or deletion of one carbon to optimize their fit to the receptor. In addition, the acyloxy group of the C region was replaced with amide and N-hydroxy amide to identify the pharmacophoric importance of the ester group in the C2 region. The results indicated that the pharmacophoric arrangement of 1 was optimal for receptor binding affinity and antagonism, and the ester of the C2 region was significant for receptor binding. Among the derivatives, compound 19 showed distinct behavior with a 2-fold improvement in antagonism but a 13-fold reduction in binding affinity compared to 1. The partial separation of pharmacophoric requirements of these two assays has been noted before and compound 19 is thus selective for the calcium entry-linked receptor population. The conformational analysis of 1 generated three distinct conformers having different types of hydrophobic interactions, which will be utilized for exploring the active conformation of the VR1 ligand.
Lee, Jeewoo,Kim, Su Yeon,Lee, Jiyoun,Kang, Myungsim,Kil, Min-Jung,Choi, Hyun-Kyung,Jin, Mi-Kyung,Wang, Yun,Toth, Attila,Pearce, Larry V.,Lundberg, Daniel J.,Tran, Richard,Blumberg, Peter M.
p. 3411 - 3420
(2007/10/03)

Hydrazinium monoformate: A new hydrogen donor. Selective reduction of nitrocompounds catalyzed by commercial zinc dust
The nitro group in aliphatic and aromatic nitro compounds also containing reducible substituents such as ethene, nitrile, acid, phenol, halogen, ester, etc., are selectively and rapidly reduced at room temperature to corresponding amines in good yields by employing hydrazinium monoformate, in the presence of commercial zinc dust. It was observed that, hydrazinium monoformate is more effective than hydrazine or formic acid and reduction of nitro group occurs without hydrogenolysis in the low cost zinc dust compared to expensive metals like palladium.
Gowda, Shankare,Gowda, B. K. Kempe,Gowda, D. Channe
p. 281 - 289
(2007/10/03)

Zinc/hydrazine: A low cost-facile system for the reduction of nitro compounds
The nitro group in aliphatic and aromatic nitro compounds also containing reducible substituents such as ethene, nitrile, carboxylic acid, phenol, halogen, ester etc., are selectively and rapidly reduced at room temperature to corresponding amines in good yields by employing 99-100% hydrazine hydrate, in the presence of commercial zinc dust. It was observed that, this system is equally compatible with existing methods, which employ expensive catalysts like palladium, platinum, ruthenium etc.
Gowda, Shankare,Gowda, D. Channe
p. 180 - 183
(2007/10/03)

A facile reduction of nitroarenes to anilines using FeCl 3·6H2O/indium
Reduction of a variety of nitroaromatic compounds to the corresponding anilines occurs chemoselectively in high yields upon treatment with a new reduction system consisting of FeCl3·6H2O/indium in aqueous methanol.
Yoo, Byung Woo,Choi, Jin Woo,Hwang, Sun Kyun,Kim, Dong Yoon,Baek, Heung Soo,Choi, Kyung Il,Kim, Joong Hyup
p. 2985 - 2988
(2007/10/03)

Magnesium/ammonium formate promoted rapid, low-cost and selective reduction of nitro compounds
The reduction of nitro compounds, both aliphatic and aromatic into corresponding amines has been achieved at room temperature in good yields by employing ammonium formate in the presence of low cost magnesium powder. The hydrogenation is fast and selective in the presence of other sensitive functionalities such as halogens, -OH, -OCH3, -CN, -COOR, -COOH etc. It was observed that, this system is equally compatible with existing methods, which employ expensive catalysts like palladium, platinum, ruthenium etc.
Srinivasa,Abiraj,Gowda, D. Channe
p. 2882 - 2884
(2007/10/03)