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Journal articles on the topic 'Nitriles – Synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Ren, Yun-Lai, Jianji Wang, Xinzhe Tian, Fangping Ren, Xinqiang Cheng, and Shuang Zhao. "Direct Conversion of Benzyl Ethers into Aryl Nitriles." Synlett 29, no. 18 (2018): 2444–48. http://dx.doi.org/10.1055/s-0037-1611062.

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A direct method was developed for the conversion of benzyl ethers into aryl nitriles by using NH4OAc as the nitrogen source and oxygen as the terminal oxidant with catalysis by TEMPO/HNO3; the method is valuable for both the synthesis of aromatic nitriles and for the deprotection of ether-protected hydroxy groups to form nitrile groups in multistep organic syntheses.

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2

Robertson, Dan E., Jennifer A. Chaplin, Grace DeSantis, et al. "Exploring Nitrilase Sequence Space for Enantioselective Catalysis." Applied and Environmental Microbiology 70, no. 4 (2004): 2429–36. http://dx.doi.org/10.1128/aem.70.4.2429-2436.2004.

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ABSTRACT Nitrilases are important in the biosphere as participants in synthesis and degradation pathways for naturally occurring, as well as xenobiotically derived, nitriles. Because of their inherent enantioselectivity, nitrilases are also attractive as mild, selective catalysts for setting chiral centers in fine chemical synthesis. Unfortunately, <20 nitrilases have been reported in the scientific and patent literature, and because of stability or specificity shortcomings, their utility has been largely unrealized. In this study, 137 unique nitrilases, discovered from screening of >600

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3

Neugebauer, Witold, Eric Pinet, Munsok Kim, and Paul R. Carey. "Modified method of synthesis of N-substituted dithioesters of amino acids and peptides in the Pinner reaction." Canadian Journal of Chemistry 74, no. 3 (1996): 341–43. http://dx.doi.org/10.1139/v96-038.

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An improved method for the synthesis of dithioesters of amino acids and peptides has been developed. The syntheses have been carried out from the nitriles. The addition of thiol to the nitrile derivative in the Pinner step of dithioester synthesis was activated with hydrogen fluoride. A few examples of dithioester synthesis using liquid HF are described. Some novel dithioesters, which are model compounds for resonance Raman spectroscopic studies of dithioacylpapain intermediates, are described. Key words: dithioesters, amino acids, Pinner reaction, HF, isotopes.

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4

Marquez, Carlos, Matthieu Corbet, Simon Smolders, Philippe Marion, and Dirk De Vos. "Double metal cyanides as heterogeneous Lewis acid catalysts for nitrile synthesis via acid-nitrile exchange reactions." Chemical Communications 55, no. 86 (2019): 12984–87. http://dx.doi.org/10.1039/c9cc05382d.

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5

Bartmann, E., J. Krause та E. Merck. "Synthesis of α,α-difluoro-nitriles from α-oxo-nitriles". Journal of Fluorine Chemistry 54, № 1-3 (1991): 384. http://dx.doi.org/10.1016/s0022-1139(00)83893-2.

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6

Danek, Stefan K., David P. Kelly, Algirdas K. Serelis, and Peter J. Steel. "Stereospecific synthesis of azo nitriles." Journal of Organic Chemistry 52, no. 13 (1987): 2911–19. http://dx.doi.org/10.1021/jo00389a047.

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7

Brackman, W., and P. J. Smit. "A new synthesis of nitriles." Recueil des Travaux Chimiques des Pays-Bas 82, no. 8 (2010): 757–62. http://dx.doi.org/10.1002/recl.19630820803.

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8

Chavan, Prashant, Suhas Pednekar, Ramesh Chaughule, and Anushree Lokur. "Microwave-assisted Efficient One-pot Synthesis of Nitriles Using Recyclable Magnetite (Fe3O4) Nanoparticles as Catalyst and Water as Solvent: A Greener Approach." Nanoscience & Nanotechnology-Asia 10, no. 4 (2020): 507–17. http://dx.doi.org/10.2174/2210681209666190218144322.

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Background: There has been an increasing curiosity over the past few years to carry out organic reactions over heterogeneous nanocatalysts. Microwave activation coupled with a nanocatalyst along with water as a reaction medium makes the process further green. Microwave activation as a green process reduces reaction times, enhances product purity and improves chemical yield. Methods: Nitrile group chemistry has been explored by many researchers across the globe owing to its interesting properties and its importance in synthetic chemistry. Despite several methods being available for the synthesi

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9

Selvam, Nagarajan Panneer, Sundar Saranya, and Paramasivan T. Perumal. "A convenient and efficient protocol for the synthesis of symmetrical N,N′-alkylidine bisamides by sulfamic acid under solvent-free conditions." Canadian Journal of Chemistry 86, no. 1 (2008): 32–38. http://dx.doi.org/10.1139/v07-134.

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A simple and convenient approach to the synthesis of symmetrical N,N′-alkylidine bisamides is described. Aromatic and aliphatic nitriles react with aromatic aldehydes in the presence of sulfamic acid to give the corresponding bisamides in moderate yields.Key words: alkylidine bisamides, nitrile, sulfamic acid.

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10

Stuart, John G., та Kenneth M. Nicholas. "Cobalt-Mediated Synthesis of Propargyl Nitriles and α-Alkoxy Propargyl Nitriles". Synthesis 1989, № 06 (1989): 454–55. http://dx.doi.org/10.1055/s-1989-27287.

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11

Ghozlan, Said Ahmed Soliman, Fatma Abd El Maksoud Abd El Aal, Mona Hassan Mohamed, and Mohamed Hilmy Elnagdi. "Nitriles in Heterocyclic Synthesis: Novel Syntheses of Functionally Substituted Isoxazoles, Pyrazoles, Pyrazines and their Condensed Derivatives." Zeitschrift für Naturforschung B 41, no. 4 (1986): 489–95. http://dx.doi.org/10.1515/znb-1986-0414.

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Novel syntheses of functionally substituted isoxazoles, pyrazoles and pyrazines have been reported utilizing ethyl tosyloximinoglyoxalate (1) and the pyridinium salt 2 as starting materials. Functionally substituted nitriles are versatile reagents and their utility in heterocyclic synthesis has received considerable recent attention [3 - 7]. In previous work we have reported several new approaches for the synthesis of azoles, azines and azoloazines utilizing simple readily obtainable polyfunctional nitriles as starting materials [8-12]. Although 1 and 2 can be readily prepared from ethyl cyano

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12

Cao, Zhicheng, Jianchao Liu, Youqun Chu, Fengming Zhao, Yinghong Zhu, and Yuanbin She. "Paired Electro-synthesis of Aryl Nitriles." Chinese Journal of Organic Chemistry 39, no. 9 (2019): 2499. http://dx.doi.org/10.6023/cjoc201903052.

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13

Kita, Yusuke. "Direct Synthesis of Nitriles from Hydrocarbons." Journal of Synthetic Organic Chemistry, Japan 72, no. 8 (2014): 940–41. http://dx.doi.org/10.5059/yukigoseikyokaishi.72.940.

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14

Kawęcki, Robert. "Facile Synthesis of Dihydropyridones from Nitriles." Synthesis 2001, no. 06 (2001): 0828–30. http://dx.doi.org/10.1055/s-2001-13413.

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15

Wang, W. T., L. L. Lin, X. H. Liu, and X. M. Feng. "ChemInform Abstract: Asymmetric Synthesis of Nitriles." ChemInform 43, no. 30 (2012): no. http://dx.doi.org/10.1002/chin.201230265.

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16

Fleming, Fraser F., and Zhiyu Zhang. "Cyclic nitriles: tactical advantages in synthesis." Tetrahedron 61, no. 4 (2005): 747–89. http://dx.doi.org/10.1016/j.tet.2004.11.012.

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17

Larock, Richard C., Qingping Tian, and Alexandre A. Pletnev. "Carbocycle Synthesis via Carbopalladation of Nitriles." Journal of the American Chemical Society 121, no. 13 (1999): 3238–39. http://dx.doi.org/10.1021/ja984086w.

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18

Rao, Sadhu Srinivas, Chittireddy Venkata Ramana Reddy, and Pramod Kumar Dubey. "An Ultrasound Mediated Green Synthesis of Benzimidazolylthiounsaturatednitriles Using Water as a Green Solvent." Organic Chemistry International 2014 (November 9, 2014): 1–5. http://dx.doi.org/10.1155/2014/403803.

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Reaction of 2-cyanothiomethylbenzimidazole 1 with an aromatic aldehydes in water under ultrasonic irradiation for 10–13 min gave the corresponding unsaturated nitriles 2a–h which is an efficient and simple method under green conditions. The unsaturated nitrile derivatives were obtained in 86–98% yield with a short reaction time without any tedious workup procedures.

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19

Foden, Callum S., Saidul Islam, Christian Fernández-García, Leonardo Maugeri, Tom D. Sheppard, and Matthew W. Powner. "Prebiotic synthesis of cysteine peptides that catalyze peptide ligation in neutral water." Science 370, no. 6518 (2020): 865–69. http://dx.doi.org/10.1126/science.abd5680.

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Peptide biosynthesis is performed by ribosomes and several other classes of enzymes, but a simple chemical synthesis may have created the first peptides at the origins of life. α-Aminonitriles—prebiotic α–amino acid precursors—are generally produced by Strecker reactions. However, cysteine’s aminothiol is incompatible with nitriles. Consequently, cysteine nitrile is not stable, and cysteine has been proposed to be a product of evolution, not prebiotic chemistry. We now report a high-yielding, prebiotic synthesis of cysteine peptides. Our biomimetic pathway converts serine to cysteine by nitril

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20

Light, Kenneth M., Yasuaki Yamanaka, Masafumi Odaka, and Edward I. Solomon. "Spectroscopic and computational studies of nitrile hydratase: insights into geometric and electronic structure and the mechanism of amide synthesis." Chemical Science 6, no. 11 (2015): 6280–94. http://dx.doi.org/10.1039/c5sc02012c.

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In addition to its activation of coordinated nitriles, nitrile hydratase utilizes a coordinated sulfenate ligand as a well-oriented nucleophile to form a five-membered intermediate which subsequently undergoes attack by H<sub>2</sub>O to ultimately form the amide product.

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21

Hinzmann, Alessa, Selina Sophie Druhmann, and Harald Gröger. "Synthesis of Bifunctional Molecules for the Production of Polymers Based on Unsaturated Fatty Acids as Bioderived Raw Materials." Sustainable Chemistry 1, no. 3 (2020): 275–89. http://dx.doi.org/10.3390/suschem1030018.

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Currently, investigations of polymer-building blocks made from biorenewable feedstocks such as, for example, fatty acids, are of high interest for the chemical industry. An alternative synthesis of nitrile-substituted aliphatic carboxylic acids as precursors for ω-amino acids, which are useful to produce polymers, was investigated starting from biorenewable fatty acids. By hydroformylation of unsaturated fatty acids or unsaturated acids being accessible from unsaturated fatty acids by cross-metathesis reactions, aldehydes are formed. In this work, the hydroformylation of such unsaturated acids

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22

S. Ibrahim, Nadia, Fathy M. Abdel Galil, Ramadan M. Abdel-Motaleb, and Mohamed H. Elnagdi. "Nitriles in Heterocyclic Synthesis: Novel Synthesis of Pyridazine Derivatives." HETEROCYCLES 24, no. 5 (1986): 1219. http://dx.doi.org/10.3987/r-1986-05-1219.

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23

Jachak, Madhukar, Martin Mittelbach, and Hans Junek. "Synthesis with Nitriles: 92. Synthesis of 5-Formylcytosine Derivatives." HETEROCYCLES 36, no. 10 (1993): 2281. http://dx.doi.org/10.3987/com-93-6416.

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24

Ibrahim, Nadia Sobhy, Fathy Mohamed Abdel-Galil, Ramadan Maawad Abdel-Motaleb, and Mohamed Hilmy Elnagdi. "Nitriles in Heterocyclic Synthesis. Novel Synthesis of Pyridazine Derivatives." Bulletin of the Chemical Society of Japan 60, no. 12 (1987): 4486–88. http://dx.doi.org/10.1246/bcsj.60.4486.

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25

Sadek, Kamal Usef, Mohamed Abdallah El-Maghraby, Maghraby Ali Selim, and Mohamed Hilmy Elnagdi. "Activated Nitriles in Heterocyclic Synthesis. Synthesis of Pyrimidine Derivatives." Bulletin of the Chemical Society of Japan 61, no. 2 (1988): 539–41. http://dx.doi.org/10.1246/bcsj.61.539.

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26

Kore, Nitin, and Pavel Pazdera. "New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for “Click” Chemistry: Synthesis of 1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5-amine." Current Organic Synthesis 15, no. 4 (2018): 552–65. http://dx.doi.org/10.2174/1570179415666180110152642.

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Aim and Objective: The aim of our work is to demonstrate catalytic application of our previously reported simple Cu(I) ion supported on weakly acidic polyacrylate resin for Azide-Alkyne cycloaddition (CuAAC), Azide-Nitrile cycloaddition and in synthesis of 1-azido-4-methoxybenzene. Material and Method: To investigate the catalytic ability of title Cu(I) catalyst we performed the reaction of different aryl azide with a broader spectrum of different terminal alkyne and nitrile compounds. Results: The title supported Cu(I) catalyzes cycloaddition reactions of aryl azide with aliphatic, aromatic,

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27

Hijji, Yousef Mohammad, Rajeesha Rajan, Hani Darwish Tabba, Imad Ali Abu-Yousef, Said Mansour, and Hamdi Ben Yahia. "Microwave assisted one pot conversion of aromatic aldehydes to nitriles." European Journal of Chemistry 9, no. 3 (2018): 269–74. http://dx.doi.org/10.5155/eurjchem.9.3.269-274.1751.

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Nitriles are versatile organic precursors in organic synthesis and have numerous applications. An efficient microwave assisted method for conversion of aromatic aldehydes to the corresponding nitriles is reported. Aldehydes are readily converted to oxime followed by acetylation and acetic acid elimination to provide nitriles in good yields within minutes. The method proved to be efficient for the synthesis of aromatic and heterocyclic nitriles. The reaction proceeds smoothly by microwave at 150 °C for 5 minutes. The obtained products are isolated simply by filtration or extraction.

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28

Lu, Jian, Dong-Huai Tu, Yang Li, et al. "Nickel-Catalyzed Addition of Arylboronic Acids to Alkyl Nitriles for Synthesis of Aryl Ketones in Fluorinated Solvent." Synlett 29, no. 05 (2017): 593–96. http://dx.doi.org/10.1055/s-0036-1589137.

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A mild and efficient nickel-catalyzed addition of arylboronic acids to alkyl nitriles in a fluorinated solvent for the synthesis of various aryl ketones is described. A broad range of arylboronic acids and alkyl nitriles were investigated, and the desired products were obtained with good to excellent yields under the optimized conditions. This method provides an opportunity for the synthesis of aryl ketones from alkyl nitriles, especially acetonitrile, with a non-noble metal catalyst in one pot.

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29

Caldarelli, Marina, Giovanni Biasoli, Paolo Cozzi, and Nicola Mongelli. "Novel synthesis of aliphatic nitriles from amidines." Tetrahedron Letters 39, no. 21 (1998): 3551–54. http://dx.doi.org/10.1016/s0040-4039(98)00546-2.

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30

Ramachandran, P. Veeraraghavan, Wataru Mitsuhashi, and Daniel R. Nicponski. "Synthesis of 2-substituted pyrrolidines from nitriles." Tetrahedron Letters 54, no. 37 (2013): 5001–3. http://dx.doi.org/10.1016/j.tetlet.2013.06.075.

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31

Wang, Mei-Xiang. "Enantioselective Biotransformations of Nitriles in Organic Synthesis." Accounts of Chemical Research 48, no. 3 (2015): 602–11. http://dx.doi.org/10.1021/ar500406s.

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32

Frutos, Rogelio P., Isabelle Gallou, Diana Reeves, Yibo Xu, Dhileepkumar Krishnamurthy, and Chris H. Senanayake. "Expedient synthesis of substituted imidazoles from nitriles." Tetrahedron Letters 46, no. 48 (2005): 8369–72. http://dx.doi.org/10.1016/j.tetlet.2005.09.153.

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33

Popov, Yu V., T. G. Korchagina, and V. S. Kamaletdinova. "Synthesis of nitriles containing 3-phenoxyphenyl fragment." Russian Journal of General Chemistry 80, no. 4 (2010): 776–80. http://dx.doi.org/10.1134/s107036321004016x.

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34

Sung, Dae Dong, Jung Ah Jang, Gui Tac Lim, et al. "A simple, effective synthesis of carborane nitriles." Mendeleev Communications 6, no. 1 (1996): 26. http://dx.doi.org/10.1070/mc1996v006n01abeh000563.

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35

Kamiñski, Rafal, Richard S. Glass, and Aleksandra Skowroñska. "A Convenient Synthesis of Selenocarboxamides from Nitriles." Synthesis 2001, no. 09 (2001): 1308–10. http://dx.doi.org/10.1055/s-2001-15232.

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36

Fleming, Fraser F., Qunzhao Wang та Omar W. Steward. "Hydroxylated α,β-Unsaturated Nitriles: Stereoselective Synthesis". Journal of Organic Chemistry 66, № 6 (2001): 2171–74. http://dx.doi.org/10.1021/jo005692o.

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37

Wang, Mei-Xiang. "Enantioselective Biotransformations of Nitriles in Organic Synthesis." Topics in Catalysis 35, no. 1-2 (2005): 117–30. http://dx.doi.org/10.1007/s11244-005-3817-1.

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38

Elagamey, Abdel Ghani A., Mamdouh A. Sofan, Zaghloul E. Kandeel, and Mohamed H. Elnagdi. "Nitriles in organic synthesis: A novel synthesis of 2-thienylbiaryls." Collection of Czechoslovak Chemical Communications 52, no. 6 (1987): 1561–65. http://dx.doi.org/10.1135/cccc19871561.

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A novel synthesis of 2-thienylbiaryls via the reaction of the 2-cyano-3-(2-thienyl)crotononitrile with cinnamonitriles is reported. The same products were also obtained from the reaction of 1,1-dicyano-2-thienyl-4-arylbuta-1,3-dienes with malononitrile or ethyl cyanoacetate.

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39

Salaheldin, Abdellatif M., Ana M. F. Oliveira-Campos, and Lígia M. Rodrigues. "Heterocyclic Synthesis with Nitriles: Synthesis of Pyrazolopyrimidine and Pyrazolopyridine Derivatives." Synthetic Communications 39, no. 7 (2009): 1186–95. http://dx.doi.org/10.1080/00397910802517814.

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40

Ji, Min, Chengliang Feng, Bin Yan, Guibo Yin, and Junqing Chen. "Fe(ClO4)3·H2O-Catalyzed Ritter Reaction: A Convenient Synthesis of Amides from Esters and Nitriles." Synlett 29, no. 17 (2018): 2257–64. http://dx.doi.org/10.1055/s-0037-1610658.

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An efficient and inexpensive synthesis of N-substituted amides from the Ritter reaction of nitriles with esters catalyzed by Fe(ClO4)3·H2O is described. Fe(ClO4)3·H2O is an economically efficient catalyst for the Ritter reaction under solvent-free conditions. Reactions of a range of esters (benzyl, sec-alkyl, and tert-butyl esters) with nitriles (primary, secondary, tertiary, and aryl nitriles) were performed to provide the corresponding amides in high to excellent yields.

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41

Abed, N. M., N. S. Ibrahim, S. M. Fahmy, and M. H. Elnagdi. "ACTIVATED NITRILES IN HETEROCYCLIC SYNTHESIS. NOVEL SYNTHESES OF PYRIMIDINES AND PYRIDINES." Organic Preparations and Procedures International 17, no. 2 (1985): 107–14. http://dx.doi.org/10.1080/00304948509355482.

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42

Eshghi, Hossein, Seyed Mohammad Seyedi, and Elaheh Rahimi Zarei. "Ferric Hydrogensulfate As a Reusable Heterogeneous Catalyst for the Synthesis of 5-Substituted-1H-Tetrazoles and Amides." ISRN Organic Chemistry 2011 (March 29, 2011): 1–5. http://dx.doi.org/10.5402/2011/195850.

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Ferric hydrogensulfate catalyzed the synthesis of 5-substituted 1H-tetrazoles via [2 + 3] cycloaddition of nitriles and sodium azide. This method has the advantages of high yields, simple methodology, and easy workup. The catalyst can be recovered by simple filtration and reused delivering good yields. Also, ferric hydrogensulfate catalyzed the hydrolysis of nitriles to primary amides under aqueous conditions. Various aliphatic and aromatic nitriles converted to the corresponding amides in good yields without any contamination with carboxylic acids.

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43

Rychnovsky, Scott D., and Sonja S. Swenson. "Tandem radical nitrile transfer-cyclization reactions of 1,3-dioxane-4-nitriles: Synthesis of spirocyclic systems." Tetrahedron 53, no. 48 (1997): 16489–502. http://dx.doi.org/10.1016/s0040-4020(97)01030-2.

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44

Veer, Sachin D., Kamlesh V. Katkar, and Krishnacharya G. Akamanchi. "Sulfated tungstate catalyzed activation of nitriles: addition of amines to nitriles for synthesis of amidines." Tetrahedron Letters 57, no. 36 (2016): 4039–43. http://dx.doi.org/10.1016/j.tetlet.2016.07.073.

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45

Mecozzi, Tiziana, Marino Petrini та Roberto Profeta. "Reaction of α-Amidoalkylphenyl Sulfones with Lithiated Nitriles: Syn-Selective Synthesis of β-Amino Nitriles". Journal of Organic Chemistry 66, № 24 (2001): 8264–67. http://dx.doi.org/10.1021/jo0160423.

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46

Mourad Sherif, Sherif, Mohamed Hilmy Elnagdi, and Rafat Milad Mohareb. "The Synthetic Potentialities of Nitriles in Heterocyclic Synthesis." HETEROCYCLES 26, no. 2 (1987): 497. http://dx.doi.org/10.3987/r-1987-02-0497.

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47

Lanari, Daniela, Matteo Alonzi, Francesco Ferlin, Stefano Santoro, and Luigi Vaccaro. "A Catalytic Peterson-like Synthesis of Alkenyl Nitriles." Organic Letters 18, no. 11 (2016): 2680–83. http://dx.doi.org/10.1021/acs.orglett.6b01121.

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48

Winkler, Margit, Ludmila Martínková, Astrid C. Knall, Stefan Krahulec та Norbert Klempier. "Synthesis and microbial transformation of β-amino nitriles". Tetrahedron 61, № 17 (2005): 4249–60. http://dx.doi.org/10.1016/j.tet.2005.02.057.

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49

Caddick, Stephen, Alexandra K. de K. Haynes, Duncan B. Judd, and Meredith R. V. Williams. "Convenient synthesis of protected primary amines from nitriles." Tetrahedron Letters 41, no. 18 (2000): 3513–16. http://dx.doi.org/10.1016/s0040-4039(00)00410-x.

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50

Nikolaev, A. E., V. E. Semenov, I. V. Galyametdinova, L. F. Saifina, D. R. Sharafutdinova, and V. S. Reznik. "Trimerization of nitriles in the synthesis of multipyrimidinophanes." Russian Journal of Organic Chemistry 49, no. 7 (2013): 1096–98. http://dx.doi.org/10.1134/s1070428013070270.

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