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Journal articles on the topic 'Cyanoacetamides'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

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

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2

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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3

Ilic, Natasa, Aleksandar Marinkovic, Dusan Mijin, Marina Nevescanin, and Slobodan Petrovic. "EI/MS/MS spectra of N-monosubstituted cyanoacetamides." Chemical Industry and Chemical Engineering Quarterly 16, no. 4 (2010): 387–97. http://dx.doi.org/10.2298/ciceq100421042i.

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The electron-ionization induced mass spectra of twenty six N-monosubstituted cyanoacetamides were recorded and their fragmentation patterns were studied. The effect of Nalkyl and N-aryl substituent to the fragmentation of the investigated compounds was discussed. Mechanistic generalization lead to a conclusion that fission of the carbon-carbon bonds next to carbonyl function or nitrogen were processes common for N-alkyl and N-(4-substituted phenyl) cyanoacetamides. In some amides, the elimination of acyl group by ketene fragment, gave rise to the more stable ion. Cycloalkyl amides could not fr

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4

Abdelhamid, Ismail Abdelshafy, Said A. S. Ghozlan, Amr M. Abdelmoniem, Muhammed A. Ramadan, Hassan M. Abdelwahab, and Mohamed Gamal Mohamed Abdelrahman. "Synthesis, and Synthetic Applications of Cyanoacetamides." Arkivoc 2020, no. 1 (2020): 297–399. http://dx.doi.org/10.24820/ark.5550190.p011.254.

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5

Renner, Alfred, Roland Moser, Miriam Bellus, Hermann Fuhrer, Othmar Hosang, and Gustav Szekely. "Cure of epoxy resins with cyanoacetamides." Journal of Polymer Science Part A: Polymer Chemistry 26, no. 5 (1988): 1361–76. http://dx.doi.org/10.1002/pola.1988.080260510.

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6

Al-Awadi, Nouria A., Mohamed H. Elnagdi, Tommy Mathew, and Mervat Abdel Khalik. "Pyrolysis of aminonitriles, cyanohydrazones, and cyanoacetamides. Part II. Elimination reactions of arylacetylhydrazone, arylcyanoacetylhydrazone, and substituted cyanoacetamides." International Journal of Chemical Kinetics 28, no. 10 (1996): 749–54. http://dx.doi.org/10.1002/(sici)1097-4601(1996)28:10<749::aid-kin5>3.0.co;2-n.

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7

Kong, Lingbin, Rong Huang, Haodan He, Yunxiang Fan, Jun Lin, and Shengjiao Yan. "Multi-component solvent-free cascade reaction of 2-cyanoacetamides: regioselective synthesis of pyridin-2-ones bearing quaternary centers." Green Chemistry 22, no. 1 (2020): 256–64. http://dx.doi.org/10.1039/c9gc03692j.

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8

Ibrahim, Hamada Mohamed, Wael Abdelgayed Ahmed Arafa, and Haider Behbehani. "l-Proline catalyzed one-pot synthesis of polysubstituted pyridine system incorporating benzothiazole moietyviasustainable sonochemical approach." RSC Advances 8, no. 66 (2018): 37606–17. http://dx.doi.org/10.1039/c8ra07013j.

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Thel-proline catalyzed ultrasonic-mediated synthesis of polysubstituted pyridone derivatives through the reaction ofN-(benzothiazol-2-yl)-2-cyanoacetamides with an assortment of arylidenes has demonstrated as an efficient protocol.

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9

Marinkovic, Aleksandar, Jelena Nedeljkovic, Dusan Mijin, Natasa Ilic, and Slobodan Petrovic. "Correlation analysis of IR, 1H and 13C NMR spectral data of N-alkyl and N-cycloalkyl cyanoacetamides." Chemical Industry and Chemical Engineering Quarterly 17, no. 3 (2011): 307–14. http://dx.doi.org/10.2298/ciceq110302016m.

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Linear free energy relationships (LFER) were applied to the IR, 1H and 13C NMR spectral data in Nalkyl and N-cycloalkyl cyanoacetamides. N-alkyl and N-cycloalkyl cyanocetamides were synthesized from corresponding amine and ethyl cyanoacetate. A number of substituents were employed for alkyl substitution, and fairly good correlations were obtained, using simple Hammett equation. In N-alkyl and N-cycloalkyl cyanoacetamides substituent cause SCS of N-H hydrogen primarily by steric interaction, polar subtituent effect influences SCS shift of C=O carbon, while steric effect of N-alkyl substituent c

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10

Adhikari, Raju, Dionne A. Jones, Andris J. Liepa та Roland H. Nearn. "Synthesis of N-Substituted γ-Methylene γ-Lactams". Australian Journal of Chemistry 58, № 12 (2005): 882. http://dx.doi.org/10.1071/ch05286.

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N-Substituted cyanoacetamides 1 were condensed with 1,2-diketones 2 under base catalysis to form γ-hydroxy γ-lactams 3. Treatment of 3 with acids gave novel fungicidal γ-methylene γ-lactams 4. The exocyclic double bond of 4b reacted reversibly with 4-toluene sulfinate.

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11

Chikava, Alexandra R., Alexei A. Dolganov, and Victor V. Dotsenko. "On the Acylation of 1,6-Diamino-2-oxo-1,2-dihydropyridine-3,5-dicarbonitriles." Chemistry Proceedings 3, no. 1 (2020): 34. http://dx.doi.org/10.3390/ecsoc-24-08315.

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Here, 1,6-diamino-2-oxo-1,2-dihydropyridine-3,5-dicarbonitriles, prepared by the reaction of cyanoacethydrazide with arylmethylene malononitriles, react with 1-cyanoacetyl-3,5-dimethylpyrazole and chloroacetyl chloride to give corresponding cyanoacetamides and chloroacetamides. The reaction with phthalic anhydride proceeds under harsh conditions to give 4,7-dioxo-4,7-dihydropyrido[1′,2′:2,3][1,2,4]triazolo[5,1-a]isoindole- 1,3-dicarbonitriles.

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12

Sanad, Sherif M. H., Ahmed H. M. Elwahy, and Ismail A. Abdelhamid. "Bis(2-cyanoacetamides): versatile precursors for bis(dihydropyridine-3,5-dicarbonitriles)." Arkivoc 2018, no. 7 (2018): 39–49. http://dx.doi.org/10.24820/ark.5550190.p010.683.

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13

Rauf, Abdul, Khalil Ahmed Nazish, Faiz-ul Hassan Nasim, Asma Yaqoob, and Ashfaq Mahmood Qureshi. "Synthesis of novel cyanoacetamides derivatives and their urease inhibition studies." European Journal of Chemistry 6, no. 2 (2015): 163–68. http://dx.doi.org/10.5155/eurjchem.6.2.163-168.1224.

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14

Alharbi, Osama, Ateyatallah Aljuhani, Ziad Moussa, Hanan I. Althagbi, and Moustafa A. Gouda. "Synthesis of new 2H-2-iminocoumarins incorporating fluorobenzene moiety." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 35, no. 02 (2025): 319. https://doi.org/10.59467/ijhc.2025.35.319.

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Fluorine plays a crucial role in modern pharmaceutical development owing to its distinct properties, such as high electronegativity and a compact atomic size. These features enable fluorine to improve a drug efficacy, selectivity, metabolic stability, and cell membrane permeability. To leverage these benefits, chromene-3-carboxamide derivatives (15a-e), incorporating a 2-fluorobenzene core, were synthesized by condensing salicylaldehydes (14a-d) or 1-hydroxy-2- naphthaldehyde (14e) with N-(2-fluorophenyl)acetamide (13) in a piperidine/ethanol mixture.. KEYWORDS :Cyanoacetamides, Chromene, Coum

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15

Wang, Kan, Eberhardt Herdtweck, and Alexander Dömling. "Cyanoacetamides (IV): Versatile One-Pot Route to 2-Quinoline-3-carboxamides." ACS Combinatorial Science 14, no. 5 (2012): 316–22. http://dx.doi.org/10.1021/co3000133.

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16

Vastag, Gyöngyi, Suzana Apostolov, Borko Matijević, and Tatjana Djaković-Sekulić. "Structure-interaction relationship study ofN-(4-phenylsubstituted) cyanoacetamides by multivariate methods." Journal of Chemometrics 30, no. 4 (2015): 210–16. http://dx.doi.org/10.1002/cem.2769.

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17

Lobodin, Vladislav V., Yuriy Yu Morzherin, Tom Blumenthal, et al. "The gas phase cyclization of deprotonated N-aryl-2-diazo-2-cyanoacetamides." Arkivoc 2005, no. 4 (2005): 189–98. http://dx.doi.org/10.3998/ark.5550190.0006.415.

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18

Zhang, Zhiguo, Can Xue, Xiao Liu, Qian Zhang, and Qun Liu. "Synthesis of polysubstituted 3H-pyrimidin-4-ones from cyanoacetamides under Vilsmeier conditions." Tetrahedron 67, no. 37 (2011): 7081–84. http://dx.doi.org/10.1016/j.tet.2011.07.006.

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19

Chigorina, E. A., A. V. Bespalov, and V. V. Dotsenko. "Synthesis and Cyclizations of N-(Thieno[2,3-b]pyridin-3-yl)cyanoacetamides." Russian Journal of General Chemistry 89, no. 10 (2019): 2018–26. http://dx.doi.org/10.1134/s1070363219100062.

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20

Wang, Fang, Bo-Lun Hu, Lizhi Liu, Hai-Yong Tu, and Xing-Guo Zhang. "One-Pot Synthesis of Quinoxalinones via Tandem Nitrosation/Cyclization of N-Aryl Cyanoacetamides." Journal of Organic Chemistry 82, no. 20 (2017): 11247–52. http://dx.doi.org/10.1021/acs.joc.7b01930.

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21

Kislyi, V. P., E. B. Danilova, E. P. Zakharov, and V. V. Semenov. "Synthesis of 4-aminoisoxazole-3-carboxamides using base-promoted nitrosation of N-substituted cyanoacetamides." Russian Chemical Bulletin 53, no. 3 (2004): 622–25. http://dx.doi.org/10.1023/b:rucb.0000035646.13790.8a.

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22

Litvinov, Victor P. "Cyanoacetamides and their thio- and selenocarbonyl analogues as promising reagents for fine organic synthesis." Russian Chemical Reviews 68, no. 9 (1999): 737–63. http://dx.doi.org/10.1070/rc1999v068n09abeh000533.

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23

Lebedev, A. T., P. A. Sharbatyan, A. G. Kazaryan, V. A. Bakulev, Yu M. Shafran, and V. S. Petrosyan. "Mass-spectrometric study of the cyclization of diazo compounds. 9. 2-Diazo-2-cyanoacetamides." Chemistry of Heterocyclic Compounds 22, no. 10 (1986): 1087–93. http://dx.doi.org/10.1007/bf00473484.

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24

Carles, Lionel, Kesavaram Narkunan, Sébastien Penlou, Laurence Rousset, Denis Bouchu, and Marco A. Ciufolini. "2-Pyridones from Cyanoacetamides and Enecarbonyl Compounds: Application to the Synthesis of Nothapodytine B." Journal of Organic Chemistry 67, no. 12 (2002): 4304–8. http://dx.doi.org/10.1021/jo025546d.

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25

Zhang, Zhiguo, Can Xue, Xiao Liu, Qian Zhang, and Qun Liu. "ChemInform Abstract: Synthesis of Polysubstituted 3H-Pyrimidine-4-ones from Cyanoacetamides under Vilsmeier Conditions." ChemInform 43, no. 5 (2012): no. http://dx.doi.org/10.1002/chin.201205190.

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26

Ke, Shaoyong. "Convenient Structural Diversity‐Guided Synthesis of Functionalized Sulfur‐Containing Heterocycles via α‐Substituted Cyanoacetamides". Journal of Heterocyclic Chemistry 54, № 3 (2016): 1957–62. http://dx.doi.org/10.1002/jhet.2792.

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27

Manikowski, Andrzej, and Zofia Kolarska. "Facile and Versatile Room-Temperature Synthesis of N,N-Disubstituted Cyanoacetamides from Malonic Ester Chloride." Synthetic Communications 39, no. 20 (2009): 3621–38. http://dx.doi.org/10.1080/00397910902788216.

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28

Matijević, Borko M., Đenđi Đ. Vaštag, Nada U. Perišić-Janjić, et al. "Solvent and structural effects on the UV absorption spectra of N-(substituted phenyl)-2-cyanoacetamides." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 117 (January 2014): 568–75. http://dx.doi.org/10.1016/j.saa.2013.08.040.

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29

Fefelova, S. R., D. A. Krasnikov, V. D. Dyachenko, and A. D. Dyachenko. "Regioselective Synthesis of Pyridin-2-One Derivatives Based on Ethyl(1-Phenylethylidene)- Cyanoacetate and Cyanoacetamides." Chemistry of Heterocyclic Compounds 50, no. 8 (2014): 1133–36. http://dx.doi.org/10.1007/s10593-014-1573-5.

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30

Marinkovic, Aleksandar, Dominik Brkic, Jelena Martinovic, Dusan Mijin, Milos Milcic, and Slobodan Petrovic. "Substituent effect on IR, 1H and 13C NMR spectral data in n-(substituted phenyl)-2-cyanoacetamides: A correlation study." Chemical Industry and Chemical Engineering Quarterly 19, no. 1 (2013): 67–78. http://dx.doi.org/10.2298/ciceq120109044m.

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Linear free energy relationships (LFER) were applied to the IR, 1H and 13C NMR spectral data of N-(substituted phenyl)-2-cyanoacetamides. A variety of substituents were employed for phenyl substitution and fairly good correlations were obtained using the simple Hammett and the Hammett-Taft dual substituent parameter equations. The correlation results of the substituent induced 13C NMR chemical shifts (SCS) of the C1, C=O and N-H atom indicated different sensitivity with respect to electronic substituent effects. A better correlation of the SCSC=O with a combination of electrophilic and nucleop

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31

Litvinov, V. P. "ChemInform Abstract: Cyanoacetamides and Their Thio- and Selenocarbonyl Analogues as Promising Reagents for Fine Organic Synthesis." ChemInform 31, no. 14 (2010): no. http://dx.doi.org/10.1002/chin.200014272.

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32

Lebedev, Albert T., Vasily A. Bakulev, Roger N. Hayes, and John H. Bowie. "Anionic rearrangement in the gas phase. The collision-induced dissociations of deprotonated 2-diazo-2-cyanoacetamides." Rapid Communications in Mass Spectrometry 5, no. 5 (1991): 234–37. http://dx.doi.org/10.1002/rcm.1290050505.

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33

DOROKHOV, V. A., S. V. BARANIN, A. DIB, and V. S. BOGDANOV. "ChemInform Abstract: Butylthiodibutylborane-Induced Dimerization of N-(2-Pyridyl)- and N-(5- Methyl-2-pyridyl)cyanoacetamides." ChemInform 23, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.199206192.

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34

Carles, Lionel, Kesavaram Narkunan, Sebastien Penlou, Laurence Rousset, Denis Bouchu, and Marco A. Ciufolini. "ChemInform Abstract: 2-Pyridones from Cyanoacetamides and Enecarbonyl Compounds: Application to the Synthesis of Nothapodytine B." ChemInform 33, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.200248148.

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35

Gao, Pei-Sen, Ning Li, Jin-Lei Zhang, et al. "Highly Efficient Palladium-Catalyzed Allylic Alkylation of Cyanoacetamides with Controllable and Chemoselective Mono- and Double Substitutions." ChemCatChem 8, no. 22 (2016): 3466–74. http://dx.doi.org/10.1002/cctc.201601021.

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36

Gao, Pei-Sen, Ning Li, Jin-Lei Zhang, et al. "Highly Efficient Palladium-Catalyzed Allylic Alkylation of Cyanoacetamides with Controllable and Chemoselective Mono- and Double Substitutions." ChemCatChem 8, no. 22 (2016): 3420. http://dx.doi.org/10.1002/cctc.201601400.

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37

Ammar, Yousry A., Samir Y. Abbas, Mostafa M. Ghorab, and Mansour S. Al Said. "Transmonocyanoacetylation of phenylenediamines: a simple and efficient synthesis of novel N-(aminophenyl)-2-cyanoacetamides and their derivatives." Tetrahedron Letters 57, no. 3 (2016): 275–77. http://dx.doi.org/10.1016/j.tetlet.2015.11.098.

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38

Wu, Zhong-Liu, та Zu-Yi Li. "Enantioselective biotransformation of α,α-disubstituted dinitriles to the corresponding 2-cyanoacetamides using Rhodococcus sp. CGMCC 0497". Tetrahedron: Asymmetry 14, № 15 (2003): 2133–42. http://dx.doi.org/10.1016/s0957-4166(03)00456-7.

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39

Yakovenko, Georgiy G., Marta S. Yagodkina, Andriy V. Bol’but, Svitlana V. Shishkina, and Mykhailo V. Vovk. "Synthesis of new triazolo[1,5-b][2,4]benzodiazepines via tandem cyclization of o-(azidomethyl)benzoates with cyanoacetamides." Monatshefte für Chemie - Chemical Monthly 148, no. 6 (2017): 1035–41. http://dx.doi.org/10.1007/s00706-016-1905-5.

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40

Kornev, Mikhail Yu, Vladimir S. Moshkin, and Vyacheslav Ya Sosnovskikh. "Synthesis of 2-amino-6-oxo-5-salicyloyl-1,6-dihydropyridine- 3-carboxamides from 3-carbamoylchromones and cyanoacetamides." Chemistry of Heterocyclic Compounds 51, no. 7 (2015): 688–90. http://dx.doi.org/10.1007/s10593-015-1758-6.

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41

Lebedev, Albert T., Tatiana N. Alekseeva, Vasiliy A. Bakulev, Mikhail Yu Kolobov, and Valeriy S. Petrosyan. "Electron impact fragmentation of isomeric 2-diazo-2-cyanoacetamides and 4-cyano-5-hydroxy-l,2,3-triazoles." Organic Mass Spectrometry 23, no. 12 (1988): 825–28. http://dx.doi.org/10.1002/oms.1210231206.

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42

Fefelova, S. R., D. A. Krasnikov, V. D. Dyachenko, and A. D. Dyachenko. "ChemInform Abstract: Regioselective Synthesis of Pyridin-2-one Derivatives Based on Ethyl(1-phenylethylidene)cyanoacetate and Cyanoacetamides." ChemInform 46, no. 16 (2015): no. http://dx.doi.org/10.1002/chin.201516215.

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43

Dorokhov, V. A., S. V. Baranin, A. Dib, and V. S. Bogdanov. "Dimerization of N-(pyrid-2-YL)- and N-(5-methylpyrid-2-YL) cyanoacetamides by the action of butylthiodibutylborane." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 40, no. 1 (1991): 152–56. http://dx.doi.org/10.1007/bf00959648.

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44

Alshaye, Najla A., Al-Shimaa Badran, and Magdy A. Ibrahim. "Linear and Angular Heteroannulated Pyridines Tethered 6-Hydroxy-4,7-Dimethoxybenzofuran: Synthesis and Antimicrobial Activity." Molecules 29, no. 18 (2024): 4496. http://dx.doi.org/10.3390/molecules29184496.

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2-Chloropyridine-3-carbonitrile derivative 1 was utilized as a key precursor to build a series of linear and angular annulated pyridines linked to a 6-hydroxy-4,7-dimethoxybenzofuran moiety. Reaction of substrate 1 with various hydrazines afforded pyrazolo[3,4-b]pyridines. Treatment of substrate 1 with 1,3-N,N-binucleophiles including 3-amino-1,2,4-triazole, 5-amino-1H-tetrazole, 3-amino-6-methyl-1,2,4-triazin-5(4H)-one and 2-aminobenzimidazole produced the novel angular pyrido[3,2-e][1,2,4]triazolo[4,3-a]pyrimidine, pyrido[3,2-e][1,2,4]tetrazolo[1,5-a]pyrimidine, pyrido[3′,2′:5,6] pyrimido[2,

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45

Abdellaoui, Hassane, та Jiaxi Xu. "Versatile synthesis of 4-spiro-β-lactam-3-carbonitriles via the intramolecular nucleophilic cyclization of N-(p-hydroxyphenyl)cyanoacetamides". Tetrahedron 70, № 29 (2014): 4323–30. http://dx.doi.org/10.1016/j.tet.2014.05.008.

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46

Yang, Jiabin, Guoqiang Su, Yu Ren, and Yang Chen. "One step synthesis of 1,5-diaryl pyridin-2(1H)-ones from 2-aryl vinamidinium salts and N-aryl cyanoacetamides." Tetrahedron 70, no. 45 (2014): 8642–47. http://dx.doi.org/10.1016/j.tet.2014.09.041.

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47

Sosnovskikh, Vyacheslav Ya, Alexander V. Safrygin, Viktor A. Anufriev, Oleg S. Eltsov, and Viktor O. Iaroshenko. "Reactions of 2-(trifluoromethyl)chromones with cyanoacetamides, ethyl cyanoacetate and diethyl malonate. Unexpected synthesis of benzo[c]coumarin derivatives." Tetrahedron Letters 52, no. 47 (2011): 6271–74. http://dx.doi.org/10.1016/j.tetlet.2011.09.082.

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48

Kornev, Mikhail Yu, Vladimir S. Moshkin, and Vyacheslav Ya Sosnovskikh. "ChemInform Abstract: Synthesis of 2-Amino-6-oxo-5-salicyloyl-1,6-dihydropyridine-3-carboxamides from 3-Carbamoylchromones and Cyanoacetamides." ChemInform 47, no. 13 (2016): no. http://dx.doi.org/10.1002/chin.201613159.

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49

Elinson, Michail N., Fedor V. Ryzhkov, Anatoly N. Vereshchagin, Sergey V. Gorbunov, and Mikhail P. Egorov. "Multicomponent assembling of salicylaldehydes, malononitrile and cyanoacetamides: A simple and efficient approach to medicinally relevant 2-amino-4H-chromene scaffold." Comptes Rendus Chimie 18, no. 5 (2015): 540–46. http://dx.doi.org/10.1016/j.crci.2014.09.005.

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50

Bogdanov, V. S., S. V. Baranin, A. Dib, I. P. Yakovlev, and V. A. Dorokhov. "Synthesis of boron chelates from N-(pyrid-2-YL)- and (N-4-methylpyrid-2-YL) cyanoacetamides and their tautomeric transformations." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 40, no. 1 (1991): 147–51. http://dx.doi.org/10.1007/bf00959647.

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