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Journal articles on the topic 'Cyanoacetamide'

Author: Grafiati

Published: 5 June 2025

Last updated: 15 July 2025

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1

Wang, Kan, Katrina Nguyen, Yijun Huang, and Alexander Dömling. "Cyanoacetamide Multicomponent Reaction (I): Parallel Synthesis Of Cyanoacetamides." Journal of Combinatorial Chemistry 11, no. 5 (2009): 920–27. http://dx.doi.org/10.1021/cc9000778.

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2

El-Behairy, Mohammed Farrag, Rasha M. Hassan, and Eirik Sundby. "Enantioselective Chromatographic Separation and Lipase Catalyzed Asymmetric Resolution of Biologically Important Chiral Amines." Separations 8, no. 10 (2021): 165. http://dx.doi.org/10.3390/separations8100165.

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Cyanoacetamides are vital synthons in synthetic organic chemistry. However, methods to enantiopure cyanoacetamides have not yet been well explored. In this work, the preparation of cyanoacetamide synthons RS-(1a–4a) or methoxyacetamides RS-(1b–4b) in enantiopure/enriched form was investigated. Compounds S-1, S-2, R-1b, R-1a, andR-2b were prepared in enantiopure form (ee > 99%) while compounds S-4, R-2a, and R-4a were achieved in ee 9%, 80%, and 76%, respectively. Many baselines enantioselective HPLC separations of amines 1–4, their cyanoacetamides (1a–4a), and methoxyacetamides (1b–4b) were achieved by utilizing diverse mobile-phase compositions and two cellulose-based CSPs (ODH® and LUX-3® columns). Such enantioselective HPLC separations were used to monitor the lipase-catalyzed kinetic resolution of amines RS-(1–4).

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3

Zdzienicka, Anna. "2-Cyanoacetamide." Synlett 24, no. 09 (2013): 1162–63. http://dx.doi.org/10.1055/s-0033-1338942.

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4

Sanz-Novo, M., I. León, J. L. Alonso, A. Largo, and C. Barrientos. "Formation of interstellar cyanoacetamide: a rotational and computational study." Astronomy & Astrophysics 644 (November 24, 2020): A3. http://dx.doi.org/10.1051/0004-6361/202038766.

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Context. Cyanoacetamide is a –CN bearing molecule that is also an amide derivative target molecule in the interstellar medium. Aims. The aim of our investigation is to analyze the feasibility of a plausible formation process of protonated cyanoacetamide under interstellar conditions and to provide direct experimental frequencies of the ground vibrational state of the neutral form in the microwave region in order to enable its eventual identification in the interstellar medium. Methods. We used high-level theoretical computations to study the formation process of protonated cyanoacetamide. Furthermore, we employed a high-resolution laser-ablation molecular beam Fourier transform spectroscopic technique to measure the frequencies of the neutral form. Results. We report the first rotational characterization of cyanoacetamide, and a precise set of the relevant rotational spectroscopic constants have been determined as a first step to identifying the molecule in the interstellar medium. We fully explored the potential energy surface to study a gas-phase reaction on the formation process of protonated cyanoacetamide. We found that an exothermic process with no net activation barrier is initiated by the high-energy isomer of protonated hydroxylamine, which leads to protonated cyanoacetamide.

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5

Kantlehner, Willi, Rüdiger Stieglitz, Hansjörg Lehmann, and Markus Vettel. "Orthoamide und Iminiumsalze, IIIC. Weitere Ergebnisse bei der Umsetzung von Orthoamiden der Alkincarbonsäuren mit CH2- und CH2/NH-aciden Verbindungen." Zeitschrift für Naturforschung B 74, no. 11-12 (2019): 925–38. http://dx.doi.org/10.1515/znb-2019-0078.

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AbstractThe 1,1-bis(dimethylamino)-1,3-butadienes (keten aminals) 11a–l are prepared from orthoamide derivatives of alkyne carbonxylic acids 9b, d, e, i and CH2-acidic compounds 10a–c, f–h, k, o. The C-silylated orthoamide derivative 9c shows an ambivalent behaviour towards CH-acidic compounds. Reactions of 9c with strong CH2-acidic compounds like the nitro alkanes 10m, n and strongly enolized carbonyl compounds as methyl acetoacetate, cyanoacetamide, dibenzoylmethane, 1,3-dimethylbarbituric acid proceed under desilylation to give the ketene aminals 11u–z. In contrast to these reactions, the C-silylated ketene aminals 11o–t are obtained from 9c and weaker CH2-acidic compounds as dimethyl malonate, cyanoacetic acid derivatives and benzylcyanides. CH2/NH2-acidic compounds [cyanoacetamide (10d) and N-ethyl-cyanoacetamide (10f)] react with the orthoamide derivatives 9b, e–g at the acidic carbon-hydrogen bond to give the ketene aminals 11ac, ad, af, ag, ai, which cyclize to the pyridones 14a–d, d–g on heating. From the reaction of the orthoamide 9d with cyanoacetamide the pyridone 14c results directly. The persubstituted pyridone derivative 19 is formed by the reaction of cyanoacetamide with a mixture of the isomeric orthoamides 15 and 16. The 5,5-diamino-2,4-pentadienamide 11v attacks the orthoamide 9a at C3/C1. In the product 20 a cross conjugated multiple bond system is formed which contains an 1-aza-2,3-diamino function and a further ketene aminal function.

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6

Prlainovic, Nevena, Dejan Bezbradica, Zorica Knezevic-Jugovic, Dusan Velickovic, and Dusan Mijin. "Enzymatic synthesis of vitamin B6 precursor." Journal of the Serbian Chemical Society 78, no. 10 (2013): 1491–501. http://dx.doi.org/10.2298/jsc130322050p.

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3-Cyano-4-ethoxymethyl-6-methyl-2-pyridone is an important precursor in the synthesis of vitamin B6, obtained in the addition reaction between 2-cyanoacetamide and 1-ethoxy-2,4-pentanedione catalyzed by lipase from Candida rugosa (triacylglycerol ester hydrolases, EC 3.1.1.3). This work shows new experimental data and mathematical modeling of lipase catalyzed synthesis of 3-cyano-4-ethoxymethyl-6-methyl-2-pyridone, starting from 1-ethoxy-2,4-pentanedione and 2-cyanoacetamide. Kinetic measurements were done at 50 oC with enzyme concentration of 1.2 % w/v. Experimental results were fitted with two kinetic models: the ordered bi-ter and ping-pong bi-ter model, and the initial rates of the reaction were found to correlate best with a ping-pong bi-ter mechanism with inhibition by 2-cyanoacetamide. Obtained specificity constants indicated that lipase from C. rugosa had higher affinity towards 1-ethoxy-2,4-pentanedione and less bulky substrates.

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7

Gandhi, Sham S., and Martin S. Gibson. "Condensation reactions of 1,1-dimorpholinoethene and of 1,1-dipiperidinoethene with carbon acids." Canadian Journal of Chemistry 65, no. 12 (1987): 2717–21. http://dx.doi.org/10.1139/v87-451.

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1,1-Dimorpholinoethene and 1,1-dipiperidinoethene condense with such compounds as malononitrile, ethyl cyanoacetate, cyanoacetamide, and diethyl malonate to give the corresponding β,β-disubstituted enamine, a molecule of morpholine or piperidine being eliminated in the process. Similar reactions with acetylacetone and ethyl acetoacetate proceed with loss of the acetyl group to give the β-substituted enamine. 1,1-Dipiperidinoethene and nitromethane give the β-nitroenamine. Secondary processes of either hydrolysis or further Michael addition and elimination are noted in condensations of 1,1-dimorpholinoethene or 1,1-dipiperidinoethene with cyanoacetamide under more basic conditions.1,1-Dipiperidinoethene is arylated at the 2-position by 2,4-dinitrochlorobenzene.

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8

NIRMALANANDA, PALIT. "A MODIFICATION OF THE GUARESCHI PYRIDINE SYNTHESIS. PART III." Journal of Indian Chemical Society Vol.26 No.10, Oct. 1949 (2022): 501–3. https://doi.org/10.5281/zenodo.7263393.

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9

Vala, Ruturajsinh M., Divyang M. Patel, Mayank G. Sharma, and Hitendra M. Patel. "Impact of an aryl bulky group on a one-pot reaction of aldehyde with malononitrile and N-substituted 2-cyanoacetamide." RSC Advances 9, no. 49 (2019): 28886–93. http://dx.doi.org/10.1039/c9ra05975j.

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10

Ibrahim, N. S., R. M. Mohareb, and H. Z. Shams. "Nitriles in Heterocyclic Synthesis: New Approaches for Synthesis of Some Pyridine Derivatives." Zeitschrift für Naturforschung B 43, no. 10 (1988): 1351–54. http://dx.doi.org/10.1515/znb-1988-1023.

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Abstract A variety of pyridines was prepared from reaction of N-benzylidenecyanoethanoic hydrazide (2) with malononitrile, benzoylacetonitrile, cyanoacetamide and cinnamonitrile derivatives. The reactivity of 2 towards a variety of ketones was studied.

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11

Tamaddon, Fatemeh, and Sajedeh Maddah-Roodan. "Advanced Guareschi–Thorpe synthesis of pyridines in green buffer, and pH-controlled aqueous medium with ammonium carbonate." RSC Advances 13, no. 35 (2023): 24846–53. http://dx.doi.org/10.1039/d3ra04590k.

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Hydroxy-cyanopyridines are easily synthesized via an advanced version of the Guareschi–Thorpe reaction by three-component condensation of alkyl cyanoacetate or cyanoacetamide with 1,3-dicarbonyls and ammonium carbonate in aqueous medium.

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12

Šafář, Peter, Pavel Čepec, František Považanec, Anna Koreňová, and Naďa Prónayová. "One-Step Synthesis of 2-Amino-3-furancarboxylic Acid Derivatives from 2-Furancarbaldehyde." Collection of Czechoslovak Chemical Communications 59, no. 11 (1994): 2481–92. http://dx.doi.org/10.1135/cccc19942481.

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Reaction of derivatives of 2-furancarbaldehyde or 2-acetylfuran with malononitrile, methyl cyanoacetate or cyanoacetamide in the presence of secondary amines afforded derivatives of 2-amino-3-furancarboxylic acid in 45 - 88% yields.

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13

Zakhari, Nashaat A. "Spectrophotometric Assay of Certain Aminoglycosides Using Cyanoacetamide." Analytical Letters 23, no. 10 (1990): 1843–56. http://dx.doi.org/10.1080/00032719008052531.

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14

Eldin, Sameer H., and Alfred Renner. "Cyanoacetamide accelerators for the epoxide/isocyanate reaction." Journal of Applied Polymer Science 41, no. 78 (1990): 1505–16. http://dx.doi.org/10.1002/app.1990.070410713.

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15

Mohareb, R. M., A. Habashi, H. Z. Shams, and S. M. Fahmy. "Polyfunctionally Substituted Pyridines from Cyanoacetamide and Cyanoacetanilide." Archiv der Pharmazie 320, no. 7 (1987): 599–604. http://dx.doi.org/10.1002/ardp.19873200706.

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16

Dotsenko, V. V., A. E. Sinotsko, E. A. Varzieva, et al. "Reaction of N,N′-diphenyldithiomalondiamide with aromatic aldehydes and cyanoacetamide." Журнал общей химии 93, no. 10 (2023): 1586–91. http://dx.doi.org/10.31857/s0044460x23100062.

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The reaction of dithiomalondianilide ( N,N′-diphenyldithiomalondiamide) with aromatic aldehydes and cyanoacetamide in the presence of morpholine c yielded previously undescribed 6-amino-4-aryl-7-phenyl-3(phenylimino)-4,7-dihydro-3 H -[1,2]dithiolo[3,4- b ]pyridine-5-carboxamides.

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17

Khazaei, Marziyeh, Mohammad Anary-Abbasinejad, Alireza Hassanabadi, and Bahareh Sadeghi. "ZnO Nanoparticles: An Efficient Reagent, Simple and One-Pot Procedure for Synthesis of Highly Functionalized Dihydropyridine Derivatives." E-Journal of Chemistry 9, no. 2 (2012): 615–20. http://dx.doi.org/10.1155/2012/780470.

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A new and efficient one-pot synthesis of dihydropyridones derivatives by four-component reaction between cyanoacetamide, aryl aldehydes, and ethyl acetoacetate with ammonium acetate using nano ZnO is described. The reaction was performed in ethanol under reflux conditions and afforded good yields of products.

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18

Mijin, Dusan, Gordana Uscumlic, and Natasa Valentic. "Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones." Journal of the Serbian Chemical Society 66, no. 8 (2001): 507–16. http://dx.doi.org/10.2298/jsc0108507m.

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A number of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones from cyanoacetamide and the corresponding alkyl ethyl acetoacetates were synthesized according to modified literature procedures. The alkyl ethyl acetoacetates were obtained by the reaction of C-alkylation of ethyl acetoacetate. An investigation of the reaction conditions for the synthesis of 4-methyl-3-cyano-6-hydroxy-2-pyridone from cyanoacetamide and ethyl acetoacetate in eight different solvents was also performed. The ultraviolet absorption spectra of synthesized pyridones were measured in nine different solvents in the range 200-400 nm. The effects of solvent polarity and hydrogen bonding on the absorption spectra are interpreted by means of linear solvation energy relationships using a general equation of the form v = vo + s?*+a?+b?, where ?* is a measure of the solvent polarity, ? is the scale of the solvent hydrogen bond donor acidities and ? is the scale of the solvent hydrogen bond acceptor basicities.

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19

Khrapova, Ekaterina A., Natalya A. Ryzhkova, Victor V. Dotsenko, and Nicolai A. Aksenov. "The Aminometylation of 4-(Alkylthio)-6-amino-2-oxo(thioxo)-1,2-dihydropyridine-3,5-dicarbonitriles." Chemistry Proceedings 3, no. 1 (2020): 30. http://dx.doi.org/10.3390/ecsoc-24-08401.

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Easily available 2-(bis(alkylthio)methylene)malononitriles react with cyanoacetamide or cyanothioacetamide to give 4-(alkylthio)-6-amino-2-oxo(thioxo)-1,2-dihydropyridine-3,5-dicarbonitriles. Upon treatment with primary amines and/or HCHO, the compounds undergo heterocyclization to afford new pyrido[1,2-a][1,3,5]triazines or ring-condensed 1,3,5,7-tetrazocine derivatives.

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20

Mourad Sherif, Sherif, Fathy Mohamed Abdel-Galil, and Mohamed Hilmy Elnagdi. "Utiliry of Cyanoacetamide and Cyanothioacetamide in Heterocyclic Synthesis." HETEROCYCLES 24, no. 7 (1986): 2023. http://dx.doi.org/10.3987/r-1986-07-2023.

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21

Yang, Jiabin, Guoqiang Su, Yu Ren, and Yang Chen. "Reaction Mechanism of Vinamidinium Salts and Cyanoacetamide Derivatives." Journal of Chemical Research 39, no. 1 (2015): 41–43. http://dx.doi.org/10.3184/174751915x14197029812826.

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22

Zingiridis, Marios, Danae Papachristodoulou, Despoina Menegaki, Konstantinos G. Froudas, and Constantinos G. Neochoritis. "Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide." Beilstein Journal of Organic Chemistry 21 (January 24, 2025): 217–25. https://doi.org/10.3762/bjoc.21.13.

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C1 chemistry has a central role in the efficient utilization of single-carbon molecules, contributing significantly to sustainability, innovation and economic growth across various sectors. In this study, we present an efficient and rapid method for synthesizing a variety of heteroannulated pyrimidones using cyanoacetamide-based multicomponent reaction (MCR) chemistry. By utilizing specific MCR-based scaffolds as precursors and employing the abundant and inexpensive formamide as a C1 feedstock under neat conditions, we were able to efficiently access substituted thieno-, quinolino- and indolopyrimidones without the need of column chromatography. Further, a single-crystal X-ray structure was obtained, revealing certain geometrical features.

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23

Wang, Kan, Dabin Kim, and Alexander Dömling. "Cyanoacetamide MCR (III): Three-Component Gewald Reactions Revisited." Journal of Combinatorial Chemistry 12, no. 1 (2010): 111–18. http://dx.doi.org/10.1021/cc9001586.

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24

Štetinová, Jarmila, Rudolf Kada, Ján Leško, Lubomír Zalibera, Dušan Ilavský, and Alexander Bartovič. "Synthesis and Properties of Substituted 1-(2-Benzothiazolyl)-2-pyridones." Collection of Czechoslovak Chemical Communications 60, no. 6 (1995): 999–1008. http://dx.doi.org/10.1135/cccc19950999.

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The studied 1-(2-benzothiazolyl)-2-pyridones Va-Vf were prepared from N-(2-benzothiazolyl)cyanoacetamide (II) which on reaction with 4-substituted benzaldehydes afforded 3-aryl-N-(2-benzothiazolyl)-2-cyano-2-propenamides IVa-IVg. Compounds IVa-IVf were cyclized with malonodinitrile in the presence of piperidine to give the corresponding pyridones Va-Vf.

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25

H., A. Latif, and A. Elrady E. "Simple synthesis of some new heterocyclic derivatives incorporation coumarin -2-one moiety." Chemistry International 3, no. 3 (2017): 487–93. https://doi.org/10.5281/zenodo.1473410.

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3-(1-ethoxy-3-oxo-3-phenylpropyle-1-enyl)-2H-coumarin-2-one (2), had been synthesized and reacted with some selected reagents such as hydrazine hydrate, urea, cyanoacetamide, cyanoacetohydrazide, orthophenylene diamine, ortho-aminophenol and 5-aminotriazole in ethanol piperidine solution to afford new multisubtituted 3-(pyrazol, pyrimidine, pyridine, diazepine, oxazepin, triazol)-2H- coumarin-2-one derivatives.

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26

Kariuki, Benson M., Bakr F. Abdel-Wahab, Hanan A. Mohamed, and Gamal A. El-Hiti. "Synthesis and Structure Determination of 2-Cyano-3-(1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl)acrylamide." Molbank 2022, no. 2 (2022): M1372. http://dx.doi.org/10.3390/m1372.

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2-Cyano-3-(1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl)acrylamide (3) was synthesized in 90% yield from condensation of equimolar equivalents of 1-phenyl-3-(thiophen-2-yl)-1H-pyrazole-4-carbaldehyde (1) and 2-cyanoacetamide (2) in boiling ethanol under basic condition for 45 min. The structure of 3 was determined using NMR spectroscopy and single crystal X-ray diffraction.

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27

Staples, Richard J., and Nicholas Vidnovio. "Crystal structure of N-(4-chlorophenyl)-2-cyanoacetamide, C9H7ClN2O." Zeitschrift für Kristallographie - New Crystal Structures 222, no. 3 (2007): 269–70. http://dx.doi.org/10.1524/ncrs.2007.0114.

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28

Dostanic, Jasmina, Natasa Valentic, Gordana Uscumlic, and Dusan Mijin. "Synthesis of 5-(substituted phenylazo)-6-hydroxy-4-methyl-3- cyano-2-pyridones from ethyl 3-oxo-2-(substituted phenyldiazenyl)butanoates." Journal of the Serbian Chemical Society 76, no. 4 (2011): 499–504. http://dx.doi.org/10.2298/jsc100618044d.

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A new procedure for the synthesis of known azo pyridone dyes is presented. A series of 5-(substituted arylazo)-6-hydroxy-4-methyl-3- cyano-2-pyridones were prepared from ethyl 3-oxo-2-(substituted phenyldiazenyl)butanoates and cyanoacetamide in acetone using potassium hydroxide as a catalyst by simple refluxing the reaction mixture. The structure of these dyes was confirmed by FT-IR, NMR and UV-Vis spectroscopy.

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29

Eriksson, Magnus, Xingzhong Zeng, Jinghua Xu, et al. "The Guareschi–Thorpe Cyclization Revisited – An Efficient Synthesis of Substituted 2,6-Dihydroxypyridines and 2,6-Dichloropyridines." Synlett 29, no. 11 (2018): 1455–60. http://dx.doi.org/10.1055/s-0037-1609685.

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DBU as base is key in a practical modified Guareschi–Thorpe cyclization of β-keto esters and 2-cyanoacetamide to allow the synthesis of substituted pyridones in good to excellent yields. The chlorination of DBU salts of pyridones with POCl3 in the presence of a quaternary ammonium salt under standard atmospheric reflux conditions as opposed to the typical pressure equipment led to high yields of substituted 2,6-dichloropyridines.

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30

Kantlehner, Willi, Jochen Mezger, Ralf Kreß, and Wolfgang Frey. "Orthoamide und Iminiumsalze, XCII. Synthese und Reaktionen von Orthoamiden aus ethinylierten Terpenderivatena." Zeitschrift für Naturforschung B 73, no. 7 (2018): 437–55. http://dx.doi.org/10.1515/znb-2018-0011.

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Abstract β-Ionone and camphor were ethynylated to give the alkynols 14, 16, 17 which can be transformed to the alkynolethers 5b, 5i, 5j, 5k, 5l, 5m by treatment with dimethylsulfate and chlorotrimethylsilane, respectively. From the alkynolethers 5h, 5i, 5j/5k, 5l/5m the orthoamide derivatives 4h, 4i, 4j/4k, 4l/4m can be prepared by treatment with N,N,N′,N′,N″,N″-hexamethylguanidinium chloride (8) in the presence of sodium hydride. The orthoamides 4h, 4i react with the sulfonamide 30 under condensation yielding the N-sulfonylated acrylamidines 31, 32. From the orthoamide 4h and p-nitroaniline the propiolamidine 29 could be obtained. The orthoamides 4j/4k and 4l/4m, react with benzamidine to give the pyrimidines 33, 34, respectively. In the reaction of malonodinitrile (9a) with the orthoamides 4i and 4j/4k, mixtures of 1,1-diamino-1,3-butadienes 36, 38 and 1,3-diamino-1,3-butadienes 37 and 39 are produced, respectively. From CH2-acidic compounds as ethylcyanacetate (9b), diethyl-malonate (9c) and nitromethane (9d) and the orthoamide 4i the 1,1-diamino-1,3-butadienes 36b–d were produced. The pyridone derivative 40 can be prepared from cyanoacetamide (9e) and the orthoamide 4i. The condensation of the orthoamides 4j/4k with cyanoacetamide (9e) affords a mixture of the pyrimidone 41 and the nicotinonitrile 42.

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31

Štetinová, Jarmila, Rudolf Kada, Ján Leško, Miloslava Dandárová, and Marcela Krublová. "Synthesis and Spectral Properties of 1-(6-Methoxy-2-benzothiazolyl)-2-pyridones." Collection of Czechoslovak Chemical Communications 61, no. 6 (1996): 921–29. http://dx.doi.org/10.1135/cccc19960921.

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Substituted 1-(6-methoxy-2-benzothiazolyl)-2-pyridones 5a-5f have been prepared from N-(6-methoxy-2-benzothiazolyl)cyanoacetamide (2) which on reactions with 4-substituted benzaldehydes gives 3-aryl-2-cyano-N-(6-methoxy-2-benzothiazolyl)-2-propenamides 4a-4g. Derivatives 4a-4f were cyclized with malonodinitrile in the presence of piperidine to give the corresponding 2-pyridones 5a-5f. The IR, UV, 1H NMR and mass spectra of the substances synthesized are discussed.

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32

KAI, Hiroyuki, Kuniyoshi NAKAYAMA, Hiroki TSUJI, Michio MASUKO, and Akira TAKASE. "Synthesis and Fungicidal Activity of 2-Alkoxyimino-2-cyanoacetamide Derivatives." Journal of Pesticide Science 23, no. 1 (1998): 44–48. http://dx.doi.org/10.1584/jpestics.23.44.

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33

Fouda, A. S., H. E. Megahed, T. Younis, and Sh Abd El-Salam. "Corrosion control of steel in HCl solutions by cyanoacetamide derivatives." Protection of Metals and Physical Chemistry of Surfaces 50, no. 2 (2014): 254–65. http://dx.doi.org/10.1134/s2070205114020075.

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34

Eberlin, Alex, and D. Lyn H. Williams. "Halogenation of enol tautomers of 2-cyanoacetamide and malonamic acid." Journal of the Chemical Society, Perkin Transactions 2, no. 7 (May 29, 2002): 1316–19. http://dx.doi.org/10.1039/b202542f.

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35

Dotsenko, V. V., A. E. Sinotsko, E. A. Varzieva, et al. "Reaction of N,N′-Diphenyldithiomalondiamide with Aromatic Aldehydes and Cyanoacetamide." Russian Journal of General Chemistry 93, no. 10 (2023): 2518–22. http://dx.doi.org/10.1134/s1070363223100067.

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36

Slouka, Jan, and Vojtěch Bekárek. "Synthesis and cyclization of some N-oxides of 2-pyridylhydrazones of mesoxalic acid derivatives." Collection of Czechoslovak Chemical Communications 53, no. 3 (1988): 626–32. http://dx.doi.org/10.1135/cccc19880626.

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Coupling of diazotized 2-aminopyridine-1-oxide with ethyl cyanoacetylcarbamate, cyanoacetamide, malononitrile, and 2-benzimidazolylacetonitrile in an acid medium afforded N-oxides of the corresponding 2-pyridylhydrazones Ia-Id, which also exist in the N-hydroxyazine tautomeric forms IIa-IId as confirmed by IR spectroscopy. Hydrazone Ia was thermally cyclized to give 2-(pyridine-1-oxide-2-yl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile (IIIa) which was converted into the corresponding thioamide IIIb, acid IIIc, and amidoxime IIId.

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37

Datta, Arup. "Bismuth (III) Triflate: A Mild, Efficient Promoter for the Synthesis of Trisubstituted Alkenes through Knoevenagel Condensation." Oriental Journal Of Chemistry 36, no. 05 (2020): 843–49. http://dx.doi.org/10.13005/ojc/360507.

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In this work, smooth efficient and eco-friendly two component coupling method is reported for the synthesis of Knoevenagel Condensation product in presence of Bi(OTf)3 catalyst under solvent free condition. Catalyst has participated in condensation between substituted aldehydes (aromatic and hetero-aromatic) and active methylene compounds (ethyl cyanoacetate, malononitrile and cyanoacetamide) effectively to generate an excellent yield of the product. Bi(OTf)3 catalyst is stable, inexpensive and easily available was used for four times in this reaction without loss of catalytic activity.

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38

Jimenez, David Esteban Quintero, Lucas Lima Zanin, Luan Farinelli Diniz, Javier Ellena, and André Luiz Meleiro Porto. "Green Synthetic Methodology of (E)-2-cyano-3-aryl Selective Knoevenagel Adducts Under Microwave Irradiation." Current Microwave Chemistry 6, no. 1 (2019): 54–60. http://dx.doi.org/10.2174/2213335606666190906123431.

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Background: The Knoevenagel condensation is an important reaction in organic chemistry because of its capacity to form new C-C bonds and its products are mainly used in organic synthesis as intermediates, due to the large number of reactions they can undergo. Based on the importance of the Knoevenagel adducts, a sustainable synthetic methodology was developed employing microwave irradiation. Objective: Develop a synthetic methodology employing microwave irradiation and green solvents to obtain Knoevenagel adducts with high yields. Methods: Knoevenagel condensation reactions were evaluated with different basic catalysts, as well as in the presence or absence of microwave irradiation. The scope of the reaction was expanded using different aldehydes, cyanoacetamide or methyl cyanoacetate. The geometry of the formed products was also evaluated. Results: After the optimization process, the reactions between aldehydes and cyanoacetamide were performed with triethylamine as catalyst, in the presence of microwave irradiation, in 35 minutes, using NaCl solution as solvent and resulted in high yields 90-99%. The reactions performed between aldehydes and methyl cyanoacetate were also performed under these conditions, but showed better yields with EtOH as solvent 70-90%. Finally, from X-ray analysis, the (E)-geometry of these compounds was confirmed. Conclusion: In this study we developed synthetic methodology of Knoevenagel condensation using triethylamine, green solvents and microwave irradiation. In 35 minutes, products with high yields (70- 99%) were obtained and the (E)-geometry of the adducts was confirmed.

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39

Krishnan, K. Gokula, V. Saravanan, C. Udhaya Kumar, and C. Ramalingan. "Fused Thiazine Tethered Metal-Free Dyes for Dye Sensitized Solar Cells: A Computational Investigation." Asian Journal of Chemistry 33, no. 10 (2021): 2373–78. http://dx.doi.org/10.14233/ajchem.2021.23340.

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Three novel cyanoacetamide decorated phenothiazines (1a-c) have been designed. Structural and photo-physical properties of the molecules 1a-c have been investigated. To better realize the charge transport process involved in the dye-sensitized solar cells (DSSCs), computational studies have been performed using B3LYP and CAM-B3LYP method for the dyes 1a-c. Theoretical findings for DSSCs include LHE (light-harvesting efficiency) and driving forces such as electron injection (ΔGinject) and dye regeneration have been calculated to envisage the most appropriate dyes for the application of DSSC.

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40

Collins, DJ, and AM James. "4-(6'-Methoxy-3',4'-dihydronaphthalen-1'-yl)butan-2-one and the Derived Guareschi Imide." Australian Journal of Chemistry 42, no. 1 (1989): 215. http://dx.doi.org/10.1071/ch9890215.

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4-(6′-Methoxy-3′,4′-dihydronaphthalen-1′-yl)butan-2-one (6b) was condensed with ethyl cyano-acetate to give a mixture of the geometric isomers of the α, β unsaturated cyano ester (8), reaction of which with the anion derived from cyanoacetamide gave the Guareschi imide (7). Attempts to hydrolyse this to 3-[2′-(6″-methoxy-3″,4″-dihydronaphthalen-1″-yl)ethyl]-3-methylglutaric acid (4) gave only polymeric material. The preparations of 2,2-ethylenedioxy-4-(6′-methoxynaphthalen-1′-yl)butane (5a) and the corresponding butanone (5b) are also described.

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41

Thabet, H. Kh, Mohd Imran, Mohd Imran, Saleh Alaql, and M. H. M. Helal. "Bis(2-cyanoacetamide) in Heterocyclic Synthesis: Synthesis of Some Bis[2-oxopyridine, 2-iminochromene, Chromeno[3,4-c]pyridine, Benzochromeno[3,4-c]pyridine] Derivatives." Oriental Journal Of Chemistry 40, no. 1 (2024): 65–73. http://dx.doi.org/10.13005/ojc/400108.

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N,N'-(methylenebis(1,4-phenylene))bis-(2-cyanoacetamide) was exploited as a precursor for synthesing some bis (benzylidene 5a-c, pyridines 7, 8, 10a,b, chromene 14, benzochromene 15) derivatives containing diphenyl-methylene spacer via the reaction with each of aromatic aldehydes, pentane-2,4-dione, acetaldehyde/ malononitrile, arylidene-malononitriles, ethyl cinnamates, 2-hydroxybenzaldehyde, and 2-hydroxy-1-naphthaldehyde). Bis(chromeno[3,4-c]pyridines 16&18) were synthesized via Michael's addition of malononitrile or ethyl cyanoacetate to bis(chromene) derivative. The newly prepared compound structures were established via ir, NMR spectroscopic data.

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42

El-Sharkawy, R., and Reda Abdullah. "Biological Activity of some Synthetic Cyanoacetamide Derivatives against some Cotton Pests." Journal of Plant Protection and Pathology 11, no. 5 (2020): 249–52. http://dx.doi.org/10.21608/jppp.2020.95610.

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43

Bayat, Mohammad, Shima Nasri, and Behrouz Notash. "Synthesis of new 3-cyanoacetamide pyrrole and 3-acetonitrile pyrrole derivatives." Tetrahedron 73, no. 11 (2017): 1522–27. http://dx.doi.org/10.1016/j.tet.2017.02.005.

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44

Lopez Aparicio, F. J., F. Santoyo Gonzalez, P. Garcia Mendoza, and J. A. Dominguez Martinez. "Synthesis of C-glycopyranosylfuran derivatives by reaction of dialdehydes with cyanoacetamide." Carbohydrate Research 147, no. 2 (1986): 237–45. http://dx.doi.org/10.1016/s0008-6215(00)90634-7.

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45

Bakulev, V. A., M. Yu Kolobov, A. N. Grishakov, and V. S. Mokrushin. "Dual reactivity of 2-diazo-2-cyanoacetamide relative to hydrogen sulfide." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 37, no. 1 (1988): 178–80. http://dx.doi.org/10.1007/bf00962685.

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46

Crowther, Roger S., and Ralph F. Wetmore. "Fluorometric assay of O-linked glycoproteins by reaction with 2-cyanoacetamide." Analytical Biochemistry 163, no. 1 (1987): 170–74. http://dx.doi.org/10.1016/0003-2697(87)90108-4.

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47

Stec, Jozef, and William H. Witola. "Alternatives to piperidine in Knoevenagel condensation of 2-cyanoacetamide with benzaldehydes." Results in Chemistry 6 (December 2023): 101212. http://dx.doi.org/10.1016/j.rechem.2023.101212.

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48

Hishmat, O. H., Kh M. A. Khalil, Sh I. El-Naem, and A. H. Abd el-Rahman. "Synthesis of Pyranobenzopyranopyridines and Benzodipyran Derivatives." Zeitschrift für Naturforschung B 41, no. 2 (1986): 252–58. http://dx.doi.org/10.1515/znb-1986-0217.

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6-Formyl-7-hydroxy-5-methoxy-2-methylchromone on bromination yields the 8-bromo derivative or the 8-bromo-6-formyl-5,7-dihydroxy derivative depending on the reaction condition. Cyclization of both leads to the corresponding 3-acetyl-, 3-benzoyl-, 3-carboxamido-, 3-carbethoxybenzodipyran derivatives.The 3-acetylbenzodipyran derivative when treated with ethyl acetoacetate or ethyl cyanoacetate in the presence of ammonium acetate yields the corresponding dihydropyranobenzopyranopyridine dione or the dihydropyranobenzopyranopyridine trione.The reaction of the 3-acetyl derivative with cyanoacetamide in the presence of ammonium acetate affords the substituted pyranobenzopyranopyridine dione.The 3-acetyl derivative undergoes self condensation to form the substituted benzopyranobenzopyran derivative.

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49

Abdelhamid, Abdou O., and Sobhi M. Gomha. "Synthesis of New Pyrazolo[1,5-a]pyrimidine, Triazolo[4,3-a]pyrimidine Derivatives, and Thieno[2,3-b]pyridine Derivatives from Sodium 3-(5-Methyl-1-phenyl-1H-pyrazol-4-yl)-3-oxoprop-1-en-1-olate." Journal of Chemistry 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/327095.

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Condensation of sodium 3-oxo-3-(1-phenyl-1H-pyrazol-4-yl)prop-1-en-1-olate (2) with several heterocyclic amines, cyanoacetamide, cyanothioacetamide, and 2-cyanoacetohydrazide gives pyrazolo[1,5-a]pyrimidines (5a–d), pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine (9), benzo[4,5]imidazo[1,2-a]pyrimidine (10), [1,2,4]triazolo[1,5-a]pyrimidine (11), and pyridine derivatives (12–14). Also, thieno[2,3-b]pyridines (15–18) were synthesized via pyridinethione (13) withα-halo ketones andα-halo ester. Structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data, alternative synthetic routes, and chemical transformation whenever possible.

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50

Almansour, Abdulrahman I., Raju Suresh Kumar, Natarajan Arumugam, Alireza Basiri, Yalda Kia, and Mohamed Ashraf Ali. "An Expedient Synthesis, Acetylcholinesterase Inhibitory Activity, and Molecular Modeling Study of Highly Functionalized Hexahydro-1,6-naphthyridines." BioMed Research International 2015 (2015): 1–9. http://dx.doi.org/10.1155/2015/965987.

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A series of hexahydro-1,6-naphthyridines were synthesized in good yields by the reaction of 3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones with cyanoacetamide in the presence of sodium ethoxide under simple mixing at ambient temperature for 6–10 minutes and were assayed for their acetylcholinesterase (AChE) inhibitory activity using colorimetric Ellman’s method. Compound4ewith methoxy substituent atortho-position of the phenyl rings displayed the maximum inhibitory activity with IC50value of 2.12 μM. Molecular modeling simulation of4ewas performed using three-dimensional structure ofTorpedo californicaAChE (TcAChE) enzyme to disclose binding interaction and orientation of this molecule into the active site gorge of the receptor.

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