100-54-9Relevant articles and documents
Metalloporphyrin catalyzed oxidation of N-hydroxyguanidines: A biomimetic model for the H2O2-dependent activity of nitric oxide synthase
Keseru, Gyoergy M.,Balogh, Gyoergy T.,Karancsi, Tamas
, p. 1775 - 1777 (2000)
A chemical model for the H2O2 promoted oxidation by nitric oxide synthase (NOS) has been developed. Biomimetic oxidations were carried out using H2O2 and tetrakis(perfluorophenyl)porphyrinato-iron(III) chloride (FeTPPF20) as a catalyst. Similarly to NOS our model system produces N(δ)-cyanoornithine, citrulline and NO from NOHA and did not oxidize arginine itself. Based on these results we propose a peroxide shunt to be involved in the catalytic cycle of NOS. To the best of our knowledge this is the first chemical system that semiquantitatively mimics NOS activity. (C) 2000 Elsevier Science Ltd. All rights reserved.
Rhenium(VII) oxo complexes as extremely active catalysts in the dehydration of primary amides and aldoximes to nitriles
Ishihara, Kazuaki,Furuya, Yoshiro,Yamamoto, Hisashi
, p. 2983 - 2986 (2002)
An economical and environmentally benign process for the preparation of nitriles by the dehydration of primary amides and aldoximes is catalyzed by rhenium(VII) oxo complexes such as perrhenic acid and trimethylsilylperrhenate (see scheme). The reaction proceeds at azeotropic reflux (with the removal of water) under essentially neutral conditions.
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Aumann,Deady
, p. 32 (1973)
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1-Cyanoimidazole as a mild and efficient electrophilic cyanating agent
Wu, Yong-Qian,Limburg, David C.,Wilkinson, Douglas E.,Hamilton, Gregory S.
, p. 795 - 797 (2000)
formula presented A mild and high-yielding cyanating reaction of amine, sulfur, and carbanion nucleophiles is reported here using 1-cyanoimidazole as an electrophilic cyanating agent.
Dispersion and 3-Picoline Ammonoxidation Investigation of V2O5/α-Al2O3 Catalysts
Reddy, Benjaram Narasimha,Reddy, Benjaram Mahipai,Subrahmanyam, Machiraju
, p. 1649 - 1655 (1991)
The effect of changing the precursor on the dispersion and 3-picoline ammonoxidation activity of various α-Al2O3 supported V2O5 catalysts has been investigated by the techniques of X-ray fluorescence, AES, SEM, EPR, XRD, oxygen chemisorption at 195 K and
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Woodward et al.
, p. 540,542 (1944)
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Iodine/aqueous NH4OAc: An improved reaction system for direct oxidative conversion of aldehydes and alcohols into nitriles
Ren, Yi-Ming,Zhu, Yi-Zhong,Cai, Chun
, p. 18 - 19 (2008)
A convenient method for direct oxidative conversion of aldehydes and alcohols into nitriles has been developed by using the inexpensive and environmentally friendly reagent I2/aqueous NH4OAc. The aqueous NH4OAc as a non-toxic cyanide source is more eco-friendly than aqueous ammonia, because gaseous ammonia evaporates easily from aqueous ammonia but not from aqueous NH4OAc.
A Selective and Mild Oxidation of Primary Amines to Nitriles with Trichloroisocyanuric Acid
Chen, Fen-Er,Kuang, Yun-Yan,Dai, Hui-Fang,Lu, Liang,Huo, Ming
, p. 2629 - 2631 (2003)
An efficient and highly selective method for the oxidative conversion of primary amines to the corresponding nitriles using trichloroisocyanuric acid in the presence of catalytic TEMPO under mild reaction conditions is described. Other functional groups such as C,C-double bonds, benzyloxy etc. were found to be unaffected under the reaction conditions. This procedure provides a new entry to the synthesis of various aliphatic, aromatic and heterocyclic nitriles in excellent yield.
Hydrothermal synthesis of microporous W-V-O as an efficient catalyst for ammoxidation of 3-picoline
Goto, Yoshinori,Shimizu, Ken-Ichi,Murayama, Toru,Ueda, Wataru
, p. 118 - 122 (2016)
W-V complex metal oxide (W-V-O) was prepared by hydrothermal synthesis method. Characterization by XRD, XPS, ICP-AES, N2 adsorption, and STEM showed that W-V-O had a layered structure with micropore. W-V-O was tested for the vapor phase ammoxid
Potassium hexacyanoferrate(II) - A new cyanating agent for the palladium-catalyzed cyanation of aryl halides
Schareina, Thomas,Zapf, Alexander,Beller, Matthias
, p. 1388 - 1389 (2004)
A new advantageous cyanating agent, potassium hexacyanoferrate(II), is described for the palladium-catalyzed cyanation of aryl halides. All cyanide ions on the iron(II) center can be transferred to the aryl halide using palladium(II) acetate and dppf as the catalyst. Under optimized reaction conditions good yields of benzonitriles and unprecedented catalyst productivities are observed.
A simple method for the synthesis of nitriles from primary amides under neutral conditions
Bose, D. Subhas,Sunder, K. Sugnana
, p. 4235 - 4239 (1999)
1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) is a very useful reagent for the preparation of nitriles in good yields under neutral conditions.
TrocCl mediated efficient synthesis of nitriles from primary amides
Bose, D. Subhas,Kumar, K. Kiran
, p. 3047 - 3052 (2000)
In order to establish a rapid conversion method of primary amides to nitriles, various types of carboxamides were treated with 2,2,2- trichloroethyl chloroformate and Et3N, as a dehydrating agent to obtain the desired nitriles in 82-95% yields.
A convenient procedure for the palladium-catalyzed cyanation of aryl halides
Sundermeier, Mark,Zapf, Alexander,Beller, Matthias
, p. 1661 - 1664 (2003)
A useful source of cyanide for the palladium-catalyzed cyanation of aryl halides is acetone cyanohydrin (see scheme; dpppe = 1,5-bis(diphenylphosphanyl) pentane, tmeda = N,N,N′,N′-tetramethylethylenediamine). The key to the success of the reaction is the slow dosage of the cyanation reagent to the reaction mixture to prevent the deactivation of the palladium catalyst caused by excess cyanide ions in solution.
Aryl chlorothionoformate: A new versatile reagent for the preparation of nitriles and isonitriles under mild conditions
Subhas Bose,Ravinder Goud
, p. 747 - 748 (1999)
Aryl chlorothionoformate is a very useful reagent for the preparation of nitriles and isonitriles in high yields under essentially neutral conditions.
Transformation of alkaloid anabasin into nicotinonitrile
Iskakova,Kagarlitskii
, p. 656 - 658 (1999)
The possibility of preparing nicotinonitrile from the natural alkaloid anabasin via oxidative ammonolysis using a vanadium - titanium catalyst (V2O5:TiO2 = 1.0:0.5) is examined.
Sulfate additives generate robust and highly active palladium catalysts for the cyanation of aryl chlorides
Shevlin, Michael
, p. 4833 - 4836 (2010)
The use of sulfate additives such as H2SO4 greatly increases the reactivity of palladium catalysts for the cyanation of aryl and heteroaryl chlorides and renders them more robust toward adventitious air. Using this method, a wide variety of aromatic and heteroaromatic nitriles were prepared in high yield.
Triphenylphosphine-iodine: An efficient reagent system for the synthesis of nitriles from aldoximes
Venkat Narsaiah,Sreenu,Nagaiah
, p. 137 - 140 (2006)
A wide range of aldoximes were smoothly converted to the corresponding nitriles with triphenylphosphine-iodine. Copyright Taylor & Francis LLC.
Development of Pd/C-catalyzed cyanation of Aryl halides
Yu, Hannah,Richey, Rachel N.,Miller, William D.,Xu, Jiansheng,May, Scott A.
, p. 665 - 668 (2011)
A practical method for palladium-catalyzed cyanation of aryl halides using Pd/C is described. The new method can be applied to a variety of aryl bromide and active aryl chloride substrates to effect efficient conversions. The process features many advantages over existing cyanation conditions and the practical utility of the process has been demonstrated on scale.
Rapid cyanation of aryl iodides in water using microwave promotion
Arvela, Riina K.,Leadbeater, Nicholas E.,Torenius, Hanna M.,Tye, Heather
, p. 1119 - 1121 (2003)
We show that using water in conjunction with microwave heating it is possible to prepare aryl nitriles from the corresponding aryl iodides rapidly and in high yield without the need for a palladium catalyst.
New method of obtaining nicotinic acid from 2-methyl-5-ethylpyridine
Suvorov,Yakovlev,Kagarlitskii,Guseinov,Kutzhanov,Kan,Lebedeva
, p. 495 - 497 (1977)
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Studies on the ammoxidation of N heterocyclic compounds. I. Vapor phase ammoxidation of 3 picoline (Japanese)
Okada,Morita,Miwa
, p. 1443 - 1450 (1972)
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A SIMPLE REDUCTION OF AROMATIC HETEROCYCLIC N-OXIDES WITH HEXAMETHYLDISILANE: REACTIONS WITH HEXAMETHYLDISILANE AND FLUORIDE ION I
Vorbrueggen, Helmut,Krolikiewicz, Konrad
, p. 5337 - 5338 (1983)
Aromatic heterocyclic N-Oxides are readily reduced at room temperature by hexamethyldisilane in the presence of fluoride ion in THF.
Preparation of nitriles from primary amides under Swern oxidation conditions
Nakajima, Noriyuki,Ubukata, Makoto
, p. 2099 - 2102 (1997)
In order to establish a mild conversion method of primary amides to nitriles, various types of carboxamides were heated under Swern oxidation conditions, (COCl)2-DMSO and Et3N, as a dehydrating agent to obtain desired nitriles in 75-96% yields.
The Semmler-Wolff Aromatization and Schmidt Reaction Applied to Some Pyridopyrazolobenzotriazines
Kocevar, Marijan,Stanovnik, Branko,Tisler, Miha
, p. 597 - 604 (1988)
Pyridopyrazolobenzotriazin-4(1H)ones were transformed via their oximes in a Semmler-Wolff aromatization process in the tetracyclic heteroaromatic amines 4 or by Schmidt reaction into a mixture of the same amine 4 and a ring enlarg
A facile microwave-assisted palladium-catalyzed cyanation of aryl chlorides
Chobanian, Harry R.,Fors, Brett P.,Lin, Linus S.
, p. 3303 - 3305 (2006)
We report an efficient method for the preparation of aryl nitriles from aryl chlorides under either microwave assisted or thermal conditions. A catalyst system comprising tris(dibenzylidene acetone)dipalladium (Pd2(dba)3) and 2-(2′,6′-dimethoxybiphenyl)dicyclohexylphosphine (S-Phos) is shown to effectively promote cyanation of various aryl chlorides with Zn(CN)2 as the cyanide source.
Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones
Ano, Yusuke,Chatani, Naoto,Higashino, Masaya,Yamada, Yuki
supporting information, p. 3799 - 3802 (2022/04/07)
The Pd-catalyzed transformation of N-phthaloyl hydrazones into nitriles involving the cleavage of an N-N bond is reported. The use of N-heterocyclic carbene as a ligand is essential for the success of the reaction. N-Phthaloyl hydrazones prepared from aromatic aldehydes or cyclobutanones are applicable to this transformation, which gives aryl or alkenyl nitriles, respectively.
Recyclable and Reusable Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O System for Cyanation of Aryl Chlorides with Potassium Ferrocyanide
Cai, Mingzhong,Huang, Bin,Liu, Rong,Xu, Caifeng
, (2021/12/03)
Pd(OAc)2/XPhos–SO3Na in a mixture of poly(ethylene glycol) (PEG-400) and water is shown to be a highly efficient catalyst for the cyanation of aryl chlorides with potassium ferrocyanide. The reaction proceeded smoothly at 100 or 120?oC with K2CO3 or KOAc as base, delivering a variety of aromatic nitriles in good to excellent yields. The isolation of the crude products is facilely performed by extraction with cyclohexane and more importantly, both expensive Pd(OAc)2 and XPhos–SO3Na in PEG-400/H2O system could be easily recycled and reused at least six times without any apparent loss of catalytic efficiency. Graphical Abstract: Palladium-catalyzed cyanation of aryl chlorides with potassium ferrocyanide leading to aryl nitriles by using Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O as a highly efficient and recyclable catalytic system is described.[Figure not available: see fulltext.]
Method for dehydrating primary amide into nitriles under catalysis of cobalt
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Paragraph 0126-0128, (2021/06/21)
The invention provides a method for dehydrating primary amide into nitrile. The method comprises the following steps: mixing primary amide (II), silane, sodium triethylborohydride, aminopyridine imine tridentate nitrogen ligand cobalt complex (I) and a reaction solvent under the protection of inert gas, carrying out reacting at 60-100 DEG C for 6-24 hours, and post-treating reaction liquid to obtain a nitrile compound (III). According to the invention, an effective method for preparing nitrile compounds by cobalt-catalyzed primary amide dehydration reaction by using the novel aminopyridine imine tridentate nitrogen ligand cobalt complex catalyst is provided; and compared with existing methods, the method has the advantages of simple operation, mild reaction conditions, wide application range of reaction substrates, high selectivity, stable catalyst, high efficiency, and relatively high practical application value in synthesis.
