cas 4421-08-3, 4-Hydroxy-3-methoxybenzonitrile

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Potassium channel activators based on the benzopyran substructure: Synthesis and activity of the C-8 substituent
The synthesis of a series of methoxy bearing 2,2-dimethyl-2H-1-benzopyrans have been achieved for testing as potassium channel activators. The synthesis involves formation of 6-cyano-8-methoxy-2,2-dimethyl-2H-1-benzopyran from vanillin, epoxidation, then ring opening of the epoxide with nitrogen nucleophiles to produce the new benzopyrans. Biological testing showed a dramatic decrease in activity thus revealing an important site of activity in this class of compounds.
Thompson, Rona,Doggrell, Sheila,Hoberg, John O.
p. 1663 - 1668
(2003)
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Transformation of aldehydes into nitriles in an aqueous medium using O-phenylhydroxylamine as the nitrogen source
The conversion of an aldehyde into a nitrile can be efficiently performed using O-phenylhydroxylamine hydrochloride in buffered aqueous solutions. The reported method is specifically optimized for aqueous-soluble substrates including carbohydrates. Several reducing sugars including monosaccharides, disaccharides, and silyl-protected saccharides were transformed into cyanohydrins in high yields. The reaction conditions are also suitable for the formation of nitriles from various types of hydrophobic aldehyde substrates. Furthermore, cyanide can be eliminated from cyanohydrins, analogous to the Wohl degradation, by utilizing a readily-removed weakly basic resin as a promoter.
Cheewawisuttichai, Thamrongsak,Hurst, Robert D.,Brichacek, Matthew
(2021/03/24)

A Molecular Iron-Based System for Divergent Bond Activation: Controlling the Reactivity of Aldehydes
The direct synthesis of amides and nitriles from readily available aldehyde precursors provides access to functional groups of major synthetic utility. To date, most reliable catalytic methods have typically been optimized to supply one product exclusively. Herein, we describe an approach centered on an operationally simple iron-based system that, depending on the reaction conditions, selectively addresses either the C=O or C-H bond of aldehydes. This way, two divergent reaction pathways can be opened to furnish both products in high yields and selectivities under mild reaction conditions. The catalyst system takes advantage of iron's dual reactivity capable of acting as (1) a Lewis acid and (2) a nitrene transfer platform to govern the aldehyde building block. The present transformation offers a rare control over the selectivity on the basis of the iron system's ionic nature. This approach expands the repertoire of protocols for amide and nitrile synthesis and shows that fine adjustments of the catalyst system's molecular environment can supply control over bond activation processes, thus providing easy access to various products from primary building blocks.
Chatterjee, Basujit,Jena, Soumyashree,Chugh, Vishal,Weyhermüller, Thomas,Werlé, Christophe
p. 7176 - 7185
(2021/06/30)

Discovery and characterization of a novel perylenephotoreductant for the activation of aryl halides
To develop a photocatalyst with catalytical activity for substrates with low reactivities is always highly desired. Herein, based on the principle of structure–property relationships, we rationally designed the natural product cercosporin, the naturally occurring perylenequinonoid pigment, to develop a novel organic perylenephotoreductant, hexacetyl reduced cercosporin (HARCP), through structural manipulation. Compared with cercosporin, HARCP shows prominent electrochemical and photophysical characteristics with greatly improved photoreductive activity, fluorescence lifetime and fluorescence quantum yield. These properties allowed HARCP as a powerful photoreductant to efficiently realize a series of benchmark reactions, including photoreduction, alkoxylation and hydroxylation to construct C–H and C–O bonds using aryl halides as substrates under mild conditions, all of which have never been achieved by the same photocatalyst. Thus, this study well supports the notion that the principle between structural manipulation and photocatalytic activity is of great significance to design customized photocatalysts for photoredox chemistry.
Guo, Baodang,Huang, Shuping,Li, Jia,Li, Min,Liu, Xuanzhong,Rao, Yijian,Wu, Yawen,Yin, Huimin,Yuan, Zhenbo,Zhang, Yan
p. 111 - 120
(2021/06/16)

HCl·DMPU-assisted one-pot and metal-free conversion of aldehydes to nitriles
We report an efficient HCl·DMPU assisted one-pot conversion of aldehydes into nitriles. The use of HCl·DMPU as both an acidic source as well as a non-nucleophilic base constitutes an environmentally mild alternative for the preparation of nitriles. Our protocol proceeds smoothly without the use of toxic reagents and metal catalysts. Diverse functionalized aromatic, aliphatic and allylic aldehydes incorporating various functional groups were successfully converted to nitriles in excellent to quantitative yields. This protocol is characterized by a broad substrate scope, mild reaction conditions, and high scalability. This journal is
Hammond, Gerald B.,Mudshinge, Sagar R.,Potnis, Chinmay S.,Xu, Bo
supporting information
p. 4161 - 4164
(2020/07/14)

Organophotoredox assisted cyanation of bromoarenes: via silyl-radical-mediated bromine abstraction
The insertion of a nitrile (-CN) group into arenes through the direct functionalization of the C(sp2)-Br bond is a challenging reaction. Herein, we report an organophotoredox method for the cyanation of aryl bromides using the organic photoredox catalyst 4CzIPN and tosyl cyanide (TsCN) as the nitrile source. A photogenerated silyl radical, via a single electron transfer (SET) mechanism, was employed to abstract bromine from aryl bromide to provide an aryl radical, which was concomitantly intercepted by TsCN to afford the aromatic nitrile. A range of substrates containing electron-donating and -withdrawing groups was demonstrated to undergo cyanation at room temperature in good yields.
Shah, Sk. Sheriff,Shee, Maniklal,Singh, N. D. Pradeep
supporting information
p. 4240 - 4243
(2020/04/22)

Novel pleconaril derivatives: Influence of substituents in the isoxazole and phenyl rings on the antiviral activity against enteroviruses
Today, there are no medicines to treat enterovirus and rhinovirus infections. In the present study, a series of novel pleconaril derivatives with substitutions in the isoxazole and phenyl rings was synthesized and evaluated for their antiviral activity against a panel of pleconaril-sensitive and -resistant enteroviruses. Studies of the structure-activity relationship demonstrate the crucial role of the N,N-dimethylcarbamoyl group in the isoxazole ring for antiviral activity against pleconaril-resistant viruses. In addition, one or two substituents in the phenyl ring directly impact on the spectrum of antienteroviral activity. The 3-(3-methyl-4-(3-(3-N,N-dimethylcarbamoyl-isoxazol-5-yl)propoxy)phenyl)-5-trifluoromethyl-1,2,4-oxadiazole 10g was among the compounds exhibiting the strongest activity against pleconaril-resistant as well as pleconaril-susceptible enteroviruses with IC50 values from 0.02 to 5.25 μM in this series. Compound 10g demonstrated markedly less CYP3A4 induction than pleconaril, was non-mutagenic, and was bioavailable after intragastric administration in mice. These results highlight compound 10g as a promising potential candidate as a broad spectrum enterovirus and rhinovirus inhibitor for further preclinical investigations.
Egorova, Anna,Ekins, Sean,Jahn, Birgit,Kazakova, Elena,Makarov, Vadim,Schmidtke, Michaela
(2019/12/28)

Iron-Promoted Decarboxylation of Arylacetic Acids for the Synthesis of Aromatic Nitriles with Sodium Nitrite as the Nitrogen Source
A new and effective method was developed for the synthesis of aromatic nitriles from arylacetic acids by using NaNO 2as the nitrogen source and Fe(OTf) 3as the promoter at 50 °C. A series of arylacetic acids underwent this transformation to give the targeted products in yields of 51-90%. Because of the mild conditions, the reaction is compatible with a broad range of functional groups, including ester, carboxy, hydroxy, acetamido, halo, nitro, cyano, methoxy, and even highly reactive formyl groups.
Shen, Zhenpeng,Liu, Wenbo,Tian, Xinzhe,Zhao, Zhe,Ren, Yun-Lai
supporting information
p. 1805 - 1808
(2020/11/02)

Highly Efficient Microwave-assisted One-Pot Synthesis of Aromatic Nitriles from Aromatic Aldehydes
A highly efficient and environmentally benign protocol is described for the microwave-assisted one-pot synthesis of aromatic nitriles from aromatic aldehydes by the reaction with hydroxylamine hydrochloride in DMSO, which involves the intermediate formation of aldoximes and subsequent dehydration. The developed synthetic methodology can be readily accomplished with various aldehydes containing both electron-donor and electron-acceptor groups, providing excellent yields of the target products in shorter reaction times (1–2 min) compared to previously reported methodologies.
Pujari,Thorat,Mahipal,Bhondwe
p. 702 - 706
(2019/07/17)

Natural-Product-Inspired Compounds as Countermeasures against the Liver Carcinogen Aflatoxin B1
Aflatoxin B1 (AfB1) ranks among the most potent liver carcinogens known, and the accidental or intentional exposure of humans and livestock to this toxin remains a serious global threat. One protective measure that had been proposed is employing small-molecule therapeutics capable of mitigating the toxicity of AfB1; however, to date, these efforts have had little clinical success. To identify molecular scaffolds that reduce the toxicity of AfB1, we developed a cell-based high-throughput high-content imaging assay that enabled our team to test natural products (pure compounds, fractions, and extracts) for protection of monolayers and spheroids composed of HepG2 liver cells against AfB1. The spheroid assay showed notable potential for further development, as it afforded greater sensitivity of HepG2 cells to AfB1, which is believed to better mimic the in vivo response of hepatocytes to the toxin. One of the most bioactive compounds to arise from this investigation was alternariol-9-methyl ether (1, purified from an Alternaria sp. isolate), which inspired the synthesis and testing of several structurally related molecules. Based on these findings, it is proposed that several types of natural and synthetic polyarene molecules that have undergone oxidative functionalization (e.g., compounds containing 3-methoxyphenol moieties) are promising starting points for the development of new agents that protect against AfB1 toxicity.
Carter, Adam C.,King, Jarrod B.,Mattes, Allison O.,Cai, Shengxin,Singh, Narender,Cichewicz, Robert H.
p. 1694 - 1703
(2019/06/08)

Thiocyanate radical mediated dehydration of aldoximes with visible light and air
We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol for a wide range of nitriles.
Ban, Yong-Liang,Dai, Jian-Ling,Jin, Xiao-Ling,Zhang, Qing-Bao,Liu, Qiang
supporting information
p. 9701 - 9704
(2019/08/15)

Process for preparing biphenyl compounds
The present invention relates to a process for preparing a compound having the formula (I), said process comprising the following steps: a) the addition of an oxygen source into a solution of a compound of formula (II), in a water-miscible solvent, b) the addition of a laccase in the solution obtained after step a); and c) the possible recovering of the compound of formula (I) thus obtained.
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Page/Page column 19

(2019/01/04)

Preparation method of 3, 4-dihydroxybenzonitrile
The invention discloses a preparation method of 3, 4-dihydroxybenzonitrile. The method comprises the following steps: taking vanillin as a starting material, enabling vanillin to react with hydroxylamine hydrochloride in a polar solvent at low temperature, and then ensuring that vanillin reacts with hydroxylamine hydrochloride at 50 to 120 DEG C, so as to prepare high-purity Chinese cymbidium nitrile; performing elimination to remove methyl with Lewis acid without separation, so as to obtain high-purity 3, 4-dioxybenzene nitrile in a high yield, with the purity reaching up to 99.0 percent. The method has the advantages that the source of raw materials is wide, the technical process is simple, and pilot scale test shows that 3, 4-dihydroxybenzonitrile is easy for industrial production.
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Paragraph 0034; 0035; 0036; 0037

(2017/09/13)

p-TsOH mediated solvent and metal catalyst free synthesis of nitriles from aldehydes via Schmidt reaction
A new and efficient protocol for the conversion of aldehyde into nitriles by modified Schmidt reaction. The reaction is carried out under solvent free condition using sodium azide as a source of nitrogen and catalysed by p-toluene sulphonic acid in presence of silica surface with no side product. This transformation gives good to excellent yield for numerous aromatic, aliphatic and heterocyclic nitriles using very simple reagent. This method has avoided the use of transition metal catalyst, toxic cyanide, hazardous solvent and offers a greener, simple and environment friendly procedure.
Mitra, Bijeta,Pariyar, Gyan Chandra,Singha, Rabindranath,Ghosh, Pranab
supporting information
p. 2298 - 2301
(2017/05/19)

Synthesis of nitrogenated lignin-derived compounds and reactivity with laccases. Study of their application in mild chemoenzymatic oxidative processes
The chemical synthesis of a series of lignin-derived nitrogenated compounds was performed in high yields (73-99%) through simple conventional chemical transformations starting from natural monomers such as vanillin, syringaldehyde or 3,4-dihydroxybenzaldehyde. The study of the vanillin-derived compounds as substrates for commercially available laccases from Trametes versicolor and Myceliophthora thermophila in oxidative transformations, generally led to the isolation of several dimeric species in high to excellent conversions (>70%), while for hydrazone derivatives a more rapidly oxidative coupling was evidenced by the formation of oligomers and/or polymers. Remarkably, vanillin was obtained due to the hydrolysis of some of the nitrogenated functional groups, such as the hydrazone or the hydrazono tetrazole. The three families of lignin-derived compounds can provide a great source of new laccase-mediator systems (LMS), the possibility of employing them for lignin modification being particularly attractive. Preliminary experiments showed promising levels of activity towards the oxidation of a monomer (veratryl alcohol, up to 70% conversion) and a dimer (adlerol, up to 22% conversion) lignin models, higher than those achieved with the natural vanillin and syringaldehyde (up to 7% conversion with veratryl alcohol and almost negligible conversion with adlerol), these processes being also highly influenced by the pH of the reaction medium.
Albarrán-Velo, Jesús,López-Iglesias, María,Gotor, Vicente,Gotor-Fernández, Vicente,Lavandera, Iván
p. 50459 - 50471
(2017/11/10)

Synthesis method of erlotinib hydrochloride
The invention discloses a synthesis method of erlotinib hydrochloride. The synthesis method comprises the following steps: (1) at a first working section: preparing 3-methoxyl-4-hydroxybenzonitrile from vanillin and hydroxylammonium chloride; (2) at a second working section: synthesizing 3,4-dihydroxybenzonitrile; (3) at a third working section: synthesizing 3,4-di(2-methoxyethoxy)phenylacetonitrile; (4) at a fourth section: synthesizing 4,5-di(2-methoxyethoxy)-2-nitrophenylacetonitrile; (5) at a fifth working section: synthesizing 4,5-di(2-methoxyethoxy)-2-aminophenylacetonitrile hydrochloride; and (6) at a sixth working section: synthesizing the erlotinib hydrochloride. The synthesis method of the erlotinib hydrochloride, disclosed by the invention, has the advantages of reasonable design, easiness of obtaining raw materials, relatively low production cost, simplicity and easiness of operation and is suitable for industrial production.
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Paragraph 0039-0042

(2017/08/31)

Fe3O4-nanoparticles catalyzed an efficient synthesis of nitriles from aldehydes
Fe3O4-CTAB NPs have been applied as a competent catalyst for one-pot synthesis of nitriles directly from aldehydes. The present investigation describes the synthesis of nitriles by combination of aromatic/aliphatic/heterocyclic aldehydes and hydroxylamine hydrochloride in the presence of iron oxide nanocatalyst in DMF under reflux condition. Fe3O4-CTAB NPs were prepared by reported method and characterized by FE-SEM, TEM, and XRD analysis. The amount of Fe in Fe3O4-CTAB was quantified by Atomic Absorption Spectroscopy (AAS). The protocol endow with excellent yield of products along with simple reaction set up and economically adept alternative approach.
Ghosh, Pranab,Saha, Bittu,Pariyar, Gyan Chandra,Tamang, Abiral,Subba, Raju
supporting information
p. 3618 - 3621
(2016/07/21)

Improved schmidt conversion of aldehydes to nitriles using azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-Propanol
The Schmidt reaction of aromatic aldehydes using a substoichiometric amount (40 mol %) of triflic acid is described. Low catalyst loading was enabled by a strong hydrogen-bond-donating solvent hexafluoro-2-propanol (HFIP). This improved protocol tolerates a broad scope of aldehydes with diverse functional groups and the corresponding nitriles were obtained in good to high yields without the need for aqueous work up.
Motiwala, Hashim F.,Yin, Qin,Aubé, Jeffrey
(2016/02/05)

Selective laccase-catalyzed dimerization of phenolic compounds derived from lignin: Towards original symmetrical bio-based (bis) aromatic monomers
A laccase-catalyzed process was developed to prepare, selectively, in high yield, dimers of lignin-based phenolic compounds without any purification. The influence of experimental parameters such as laccase loading, nature of solvent and the presence of oxygen on the conversion of vanillin was investigated. After the dimerization, the product obtained as a precipitate is filtered off and the solution containing the enzyme can be re-used several times, which improves the process economics. A phenolic-substrate screening reveals that such process enables to dimerize regioselectively, six ortho-methoxy-para-substituted phenols (vanillin, 4-hydroxy-3-methoxybenzonitrile, acetovanillon, methyl vanillate, 2-methoxy-4-methylphenol, and eugenol) with yields ranging from 87% to 96% and one ortho-disubstituted phenol (2,6-dimethoxyphenol) with 80% yield.
Llevot, Audery,Grau, Etienne,Carlotti, Stéphane,Grelier, Stéphane,Cramail, Henri
p. 34 - 41
(2016/01/25)

FeCl3-silica: A green approach for the synthesis of nitriles from oximes
A green and suitable protocol for the conversion of aldoximes into nitriles is described. The transformation is carried out under solvent-free conditions using FeCl3-silica medium. The protocol offers a green, single-step facile procedure with the use of less toxic metal salt to isolate nitriles in good to excellent yields.
Ghosh, Pranab,Pariyar, Gyan Chandra,Saha, Bittu,Subba, Raju
supporting information
p. 685 - 691
(2016/06/08)

"Nanorust"-catalyzed benign oxidation of amines for selective synthesis of nitriles
Organic nitriles constitute key precursors and central intermediates in organic synthesis. In addition, nitriles represent a versatile motif found in numerous medicinally and biologically important compounds. Generally, these nitriles are synthesized by traditional cyanation procedures using toxic cyanides. Herein, we report the selective and environmentally benign oxidative conversion of primary amines for the synthesis of structurally diverse aromatic, aliphatic and heterocyclic nitriles using a reusable "nanorust" (nanoscale Fe2O3)-based catalysts applying molecular oxygen.
Jagadeesh, Rajenahally V.,Junge, Henrik,Beller, Matthias
p. 92 - 96
(2015/02/19)

Visible-light-mediated efficient conversion of aldoximes and primary amides into nitriles
A photosensitization-based approach for a convenient and efficient conversion of aldoximes and primary amides into nitriles is reported. The protocol involves eosin Y catalysed, visible-light-mediated in situ formation of the Vilsmeier-Haack reagent from CBr4 and a catalytic amount of DMF, which brings about the desired transformation to afford nitriles at r.t.
Yadav, Arvind K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
p. 4181 - 4186
(2014/01/06)

FeCl3 mediated one-pot route to nitriles
A new and convenient protocol for the transformation of aldehydes into nitriles using hydroxylamine hydrochloride by iron III chloride is presented. The protocol offers a very simple, cost efficient, and environmentally benign procedure with good to excellent yield of nitrile.
Ghosh, Pranab,Subba, Raju
supporting information
p. 4885 - 4887
(2013/08/28)

Combustion-derived CuO nanoparticles: An effective and environmentally benign catalyst in the synthesis of aromatic nitriles from aromatic aldehydes
CuO nanoparticles were synthesized using an energy-efficient and rapid solution combustion technique with malic acid employed as a fuel. The combustion-derived CuO nanoparticles were used as catalysts in a one-pot synthesis of aromatic nitriles from aromatic aldehydes and hydroxylamine hydrochloride. The catalyst was characterized by X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray analysis, transmission electron microscopy, and Brunauer-Emmett-Teller surface area analysis. The catalytic activity of the CuO nanoparticles in the synthesis of aromatic nitriles from aromatic aldehydes was evaluated. The present protocol offers the advantages of a clean reaction, simple methodology, short reaction duration (1-2 min), and high yield (85%-98%). The catalytic activity of the CuO nanoparticles was found to be higher than that of bulk CuO powder under the same conditions. The catalyst can also be recovered and reused up to four times with no significant loss of catalytic activity. The present approach is inexpensive and is a convenient technique suitable for industrial production of CuO nanoparticles and nitriles.
Anandakumar, Belladamadu Siddappa,Reddy, Muthukur Bhojegowd Madhusudana,Tharamani, Chikka Nagaiah,Pasha, Mohamed Afzal,Chandrappa, Gujjarahalli Thimmanna
p. 704 - 710
(2013/08/25)

K4[Fe(CN)6] as non-toxic source of cyanide for the cyanation of aryl halides using Pd-Beta zeolite as a heterogeneous catalyst
A new method for the synthesis of aryl nitriles has been developed by the reaction of aryl halides with K4Fe(CN)6 in the presence of Pd-Beta zeolite as efficient and recyclable catalyst.
Sajadi, S. Mohammad,Maham, Mehdi,Mahmoud, Sarbast Ahmad
p. 620 - 622
(2013/11/06)

SOCl 2/β-cyclodextrin: A new and efficient catalytic system for Beckmann rearrangement and dehydration of aldoximes under aqueous condition
A rapid and efficient synthesis of amides via Beckmann rearrangement of ketoximes and dehydration of aldoximes to corresponding nitriles with good to excellent yields has been carried out in the presence of SOCl 2/β-cyclodextrin under aqueous conditions. The β-cyclodextrin has been recovered and reused. Copyright Taylor & Francis Group, LLC.
Patil, Dipak,Dalal, Dipak
p. 118 - 128
(2012/10/30)

Acetohydroxamic acid: A new reagent for efficient synthesis of nitriles directly from aldehydes using Bi(OTf)3 as the catalyst
An efficient method for the preparation of nitriles directly from aldehydes by reaction with AHA using Bi(OTf)3 as the catalyst is described. Bi(OTf)3 is shown to be an efficient catalyst also for the conversion of aldoximes into nitriles.
Sridhar, Madabhushi,Reddy, Mallu Kishore Kumar,Sairam, Vangipuram Venkata,Raveendra, Jillella,Godala, Kondal Reddy,Narsaiah, Chinthala,Ramanaiah, Beeram China,Reddy, Cirandur Suresh
experimental part
p. 3421 - 3424
(2012/08/08)

One pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride using ferrous sulphate in DMF under reflux condition
A rapid and facile one pot synthesis of nitrile has been carried out in high yields from the corresponding aldehydes and hydroxylamine hydrochloride in the presence of anhydrous ferrous sulphate and DMF under reflux condition.
Patil, Dinanath D.,Wadhava, Gurumeet C.,Deshmukh, Arun K.
experimental part
p. 1401 - 1402
(2012/08/28)

An efficient and solvent-free one-pot synthesis of nitriles from aldehydes
Aldehydes are converted into corresponding nitriles in high yields by a one-pot solvent-free reaction with hydroxylamine hydrochloride in the presence of catalytic amount of pyridine under microwave irradiation. The reactions go to completion within one minute. The process is green, efficient and inexpensive.
Pasha,Nizam, Aatika
experimental part
p. 1127 - 1129
(2010/11/02)

Efficient and high-yielding protocol for the synthesis of nitriles from aldehydes
An operationally simple and high-yielding procedure has been developed for the conversion of araldehydes into the corresponding nitriles using p-toluenesulfonic acid (p-TSA) (a mild catalyst) under microwave irradiation. The products are characterized by infrared spectral analysis and by comparison of the melting and boiling points with the reported values. Copyright
Reddy, M. B. Madhusudana,Pasha
experimental part
p. 3384 - 3389
(2010/12/25)

Solvent free, microwave assisted conversion of aldehydes into nitriles and oximes in the presence of NH2OH · HCl and TiO2
Aromatic aldehydes bearing electron-donating groups are easily converted into their respective nitriles using NH2OH · HCl and TiO 2 under microwave irradiation, while those bearing an electron-withdrawing group give the corresponding oximes.
Hoelz, Lucas Villas-Boas,Goncalves, Biank Tomaz,Barros, Jose Celestino,Silva, Joaquim Fernando Mendes Da
experimental part
p. 94 - 99
(2010/05/18)

Zinc chloride-catalyzed expeditious route to nitriles
Zinc chloride has been found to be an excellent catalyst for a one-pot synthesis of nitriles from araldehydes and hydroxylammonium chloride under solvent-free conditions. The features of the present method are short reaction time, easy workup procedure, and good yields of the nitriles.
Paesha,Nizam, Aatika
scheme or table
p. 1276 - 1279
(2010/06/20)

Microwave-enhanced and ligand-free copper-catalyzed cyanation of aryl halides with K4[Fe(CN)6] in water
Copper-catalyzed cyanation of aryl halides was improved to be more economical and environmentally friendly by using water as the solvent and ligand-free Cu(OAc)2·H2O as the catalyst under microwave heating. The suggested methodology
Ren, Yunlai,Wang, Wei,Zhao, Shuang,Tian, Xinzhe,Wang, Jianji,Yin, Weiping,Cheng, Lin
supporting information; experimental part
p. 4595 - 4597
(2009/10/18)

Ligand-free Cu-catalyzed cyanation of aryl halides with K 4[Fe(Cn)6] in water
A simple methodology for Cu-catalyzed cyanation of aryl halides with K 4[Fe(CN)6] was developed with water as the solvent in conjunction with ligand-free Cu(OAc)2·H2O as the catalyst. The suggested methodology i
Ren, Yunlai,Zhao, Shuang,Tian, Xinzhe,Liu, Zhifei,Wang, Jianji,Yin, Weiping
scheme or table
p. 564 - 567
(2010/04/23)

Ionic liquid-promoted dehydration of aldoximes: a convenient access to aromatic, heteroaromatic and aliphatic nitriles
A simple and convenient procedure for the synthesis of nitriles by dehydration of aldoximes using an ionic liquid, 1-pentyl-3-methylimidazolium tetrafluoroborate, [pmim]BF4 under organic solvent-free condition, has been developed. A variety of aromatic, heteroaromatic and aliphatic aldoximes are converted to the corresponding nitriles. The ionic liquid is recovered and reused for subsequent reactions.
Saha, Debasree,Saha, Amit,Ranu, Brindaban C.
experimental part
p. 6088 - 6091
(2010/03/03)

High-yielding cleavage of (aryloxy)acetates
A reliable and high-yielding one-pot sequence for the removal of O-carboxymethyl moieties from phenols is presented. When diethylphosphoryl azide is employed as the azide transfer reagent in the Curtius rearrangement and glycerol in the subsequent hydrolytic workup, the protocol can be reliably applied to a very broad scope of substrates. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Spurg, Anke,Waldvogel, Siegfried R.
p. 337 - 342
(2008/09/18)

Acetonitrile: A convenient reagent for the one-pot preparation of perfumery nitriles from aldehydes
Various aryl and alkyl nitriles have been prepared in high yields in one-pot process by refluxing various aldehydes and hydroxylamine hydrochloride in acetonitrile.
Kanetkar, Vinod R.,Zope, Dhananjay D.,Subrahmanyam
p. 1317 - 1318
(2007/10/03)

Microwave-assisted efficient one-pot synthesis of nitriles from aldehydes in the presence of P2O5/SiO2 in solvent-free media
A rapid and efficient procedure is developed for a one-pot synthesis of nitrites by condensation of aldehydes with hydroxylamine hydrochloride in the presence of P2O5/SiO2 in solvent-free media under microwave irradiation. Copyright Taylor & Francis Inc.
Eshghi, Hossein,Gordi, Zinat
p. 619 - 623
(2007/10/03)

Design and synthesis of low molecular weight compounds with complement inhibition activity
An attempt was made to synthesize a series of non-cytotoxic low molecular weight compounds of varying substitutions and functionalities having pharmacophore activity like carbonyl compounds, carboxylic acid and bioisosteres like tetrazole and phenyl acrylic acid. The in vitro assay of these analogues for the inhibition of complement activity revealed significant inhibitory activity for varying substituents and, particularly, for bioisosteres, that is, tetrazole and phenyl acrylic acid derivatives.
Master, Hoshang E.,Khan, Shabana I.,Poojari, Krishna A.
p. 4891 - 4899
(2007/10/03)

Process for preparing 3,4-dihydroxy-benzonitrile
A process for preparing 3,4-dihydroxybenzonitrile includes the steps of reacting a nitrile compound with an alkali metal halide, followed by treating with an acid.
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(2008/06/13)

One-pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride over silica gel, montmorillonites K-10, and KSF catalysts in dry media under microwave irradiation
A rapid and facile one-pot synthesis of nitriles has been carried out from the corresponding aldehydes and hydroxylamine hydrochloride in the presence of environmentally benign silica gel (84-95%), Mont K-10 (85-96%), and Mont KSF clay (88-98%) catalysts in dry media under microwave irradiation.
Dewan, Sharwan K.,Singh, Ravinder,Kumar, Anil
p. 2025 - 2029
(2007/10/03)

An efficient method for the preparation of nitriles via the dehydration of aldoximes with phthalic anhydride
A new and highly efficient method for the conversion of aldoximes to nitriles was established. By fusing with phthalic anhydride, aldoximes were efficiently and smoothly converted into nitriles, in high yields (over 85%) and in a short time (within 5 minutes). The mixture of phthalic anhydride, a cyclic anhydride, and aldoximes in fusing state set up an ideal transition state for a selective [3.3]-sigmatropic rearrangement of the acylated aldoximes to nitriles.
Wang, Eng-Chi,Huang, Keng-Shiang,Chen, Hsing-Ming,Wu, Chung-Chin,Lin, Gwo-Jiun
p. 619 - 627
(2007/10/03)

Efficient and Rapid One-pot Conversions of Aldehydes into Nitriles and Ketones into Amides Using Silica Chloride under Microwave Irradiation
Under solvent free conditions, several aldehydes and ketones were efficiently and rapidly converted into the corresponding nitriles and amides respectively by treatment with hydroxylamine hydrochloride under microwave irradiation using silica chloride as catalyst. The yields of the products were very high and the time required for their preparation was very short compared to conventional heating experiments.
Srinivas,Mahender,Das, Biswanath
p. 738 - 739
(2007/10/03)

Practical synthesis of a highly functionalized thiazole ketone
Compound 1 is a uniquely substituted ketone prepared via addition of a thiazole anion to an aromatic nitrile in good overall yield. An exploration into the generality of the addition of thiazole anions to nitriles allowed us to make a variety of thiazole ketones in good to excellent yields. The non-odorous thiolate-mediated demethylation reaction used in the synthesis of 1 is also presented.
Frey, Lisa F.,Marcantonio, Karen M.,Chen, Cheng-Yi,Wallace, Debra J.,Murry, Jerry A.,Tan, Lushi,Chen, Weirong,Dolling, Ulf H.,Grabowski, Edward J. J.
p. 6363 - 6373
(2007/10/03)

Beckmann reaction of oximes catalysed by chloral: Mild and neutral procedures
A variety of ketoximes undergo the Beckmann rearrangement when heated with 0.5 molar equiv. of chloral (neat melt/～130°C), to furnish the corresponding amides in excellent yields (generally 80-95%) after simple work-up. (Aromatic aldoximes dehydrated to the corresponding nitriles in excellent yields under similar conditions.) The absence of solvent, Br?nsted acids, strong Lewis acids and by-products, and a simple work-up characterise the procedures.
Chandrasekhar, Sosale,Gopalaiah, Kovuru
p. 755 - 756
(2007/10/03)

Synthesis of nitriles from aldoximes using silica gel as catalyst under microwave irradiation
A rapid and efficient synthesis of nitriles via dehydration from the corresponding aldoximes has been carried out in the presence of Silica gel as catalyst under microwave irradiation in 83-95% yield.
Dewan, Sharwan K.,Singh, Ravinder
p. 3085 - 3088
(2007/10/03)

Highly convenient and efficient one-pot conversions of aldehydes into nitriles and ketones into amides using HY-zeolite
One-pot conversions of aldehydes into nitriles and ketones into amides have been carried out conveniently and efficiently using HY-zeolite as catalyst. Both microwave irradiation and conventional methods have been studied.
Srinivas,Reddy, E. Bolla,Das, Biswanath
p. 625 - 627
(2007/10/03)

bis(trichloromethyl)carbonate, an efficient activator for the one-pot conversion of aldehydes into nitriles under mild conditions
A single step conversion of aldehydes into the corresponding nitriles has been achieved in high yields using stoichiometric amounts of NH2OH·HCl, Et3N and bis(trichloromethyl)-carbonate at room temperature.
Bose, D. Subhas,Goud, P. Ravinder
p. 3621 - 3624
(2007/10/03)

Diethyl chlorophosphite: A versatile reagent
Diethyl chlorophosphite (DECP) was previously described as a reducing agent for nitro compounds to the corresponding amines (Fischer, B.; Sheihet, L. J. Org. Chem. 1998, 63, 393). Here, the utility of this reagent was extended to chemical conversions of other oxygenated functional groups. In this paper we report on the scope of the reaction of DECP with N-oxides, epoxides, sulfones, sulfoxides, hydroxylamines, ketoximes, and aldoximes. The chemoselectivity of DECP is described, and conditions for a stepwise multiple conversion of functional groups on the same molecule with this reagent are provided.
Jie, Zhou,Rammoorty, Vebumani,Fischer, Bilha
p. 711 - 719
(2007/10/03)

Mild, efficient, and rapid dehydration of aldoximes to nitriles mediated by phthalic anhydride under microwave irradiation
Aldoximes can be efficiently and rapidly dehydrated to nitriles by treatment with phthalic anhydride under microwave irradiation.
Hekmatshoar,Heravi,Beheshtiha,Asadolah
p. 111 - 114
(2007/10/03)