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Journal articles on the topic 'Malononitrile'

Author: Grafiati

Published: 4 June 2021

Last updated: 27 July 2025

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1

Zanardi, Franca, Claudio Curti, Andrea Sartori та Lucia Battistini. "Exploring the Remote Reactivity of π-Extended Carbonyl Compounds: The Vinylogous Alkylidene Malononitrile Activation Strategy". Synlett 29, № 03 (2017): 266–81. http://dx.doi.org/10.1055/s-0036-1589125.

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The installation of malononitrile into π-extended carbonyl compounds gives rise to vinylogous alkylidene malononitriles (also known as π-extended dicyanovinylidenes), the direct functionalization of which at remote C(sp3) pronucleophilic sites becomes possible and viable. Starting from easily accessible representative polyunsaturated malononitriles, mild conditions were found to directly couple them to complementary enal acceptors. In all cases, the malononitrile handle proved an indispensable (and optionally traceless) activating ingredient for the vinylogous reactions to proceed efficiently

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2

Szwed, Krystyna Bogdanowicz, Hanna Feret, and Małgorzata Lipowska. "The Reaction of Malononitrile with Some Enamines of 1-Indanone Synthesis of o-Aminonitriles of Indenopyridine and Indenothiopyran." Zeitschrift für Naturforschung B 42, no. 5 (1987): 623–27. http://dx.doi.org/10.1515/znb-1987-0518.

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(4).The reaction of enamines of 1-oxo-indan-2-carboxylic acid anilides (1) with malononitrile yielded 2-arylcarbamylindenylidene-malononitriles (3), which in alkaline solution underwent cyclization to indenopyridines Enamines of 1-oxo-indan-2-carbothionic acid anilides (2) reacted with malononitrile yielding indenothiopyrans (6), which under influence of alkalis were transformed to indenopyridines (8).

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3

Reddy Gajulapalli, V. Pratap, Poopathy Vinayagam, and Venkitasamy Kesavan. "Enantioselective assembly of functionalized carbocyclic spirooxindoles using anl-proline derived thiourea organocatalyst." RSC Advances 5, no. 10 (2015): 7370–79. http://dx.doi.org/10.1039/c4ra13711f.

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4

Dotsenko, Victor V., Inessa A. Kotlova, Nikolai A. Aksenov, and Inna V. Aksenova. "Synthesis of (3-Cyano-5,6,7,8-Tetrahydroquinolin-2(1H)-ylidene) Malononitriles." Proceedings 41, no. 1 (2019): 32. http://dx.doi.org/10.3390/ecsoc-23-06524.

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5

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 com

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6

Dhivare, Ravindra S., and S. S. Rajput. "Malononitrile: A Versatile Active Methylene Group." International Letters of Chemistry, Physics and Astronomy 57 (August 2015): 126–44. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.57.126.

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The title role of malononitrile in the development of Knoevenagel condensation of organic synthesis and their new findings are explored in this review. The active methylene group of malononitriles is very important attacking part in the heterocyclic conversions and also having a great potency towards several microbial and biological systems.

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7

Dhivare, Ravindra S., and S. S. Rajput. "Malononitrile: A Versatile Active Methylene Group." International Letters of Chemistry, Physics and Astronomy 57 (August 4, 2015): 126–44. http://dx.doi.org/10.56431/p-5354je.

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The title role of malononitrile in the development of Knoevenagel condensation of organic synthesis and their new findings are explored in this review. The active methylene group of malononitriles is very important attacking part in the heterocyclic conversions and also having a great potency towards several microbial and biological systems.

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8

R., S. Dhivare, and S. Rajput S. "Malononitrile: A Versatile Active Methylene Group." International Letters of Chemistry, Physics and Astronomy 57 (August 4, 2015): 126–44. https://doi.org/10.18052/www.scipress.com/ilcpa.57.126.

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Abstract: The title role of malononitrile in the development of Knoevenagel condensation of organic synthesis and their new findings are explored in this review. The active methylene group of malononitriles is very important attacking part in the heterocyclic conversions and also having a great potency towards several microbial and biological systems.

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9

Saikia, Anil. "Malononitrile." Synlett, no. 12 (2004): 2247–48. http://dx.doi.org/10.1055/s-2004-832822.

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10

Kozyrod, RP, J. Morgan та JT Pinhey. "The C-Arylation of α-Cyano Esters and Malononitriles by Aryllead(IV) Triacetates". Australian Journal of Chemistry 44, № 3 (1991): 369. http://dx.doi.org/10.1071/ch9910369.

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The arylation of soft carbon nucleophiles by aryllead (IV) triacetates has been extended to α- cyano esters and malononitriles. Arylation did not occur with the parent compounds, ethyl cyanoacetate and malononitrile, but in both series monosubstituted compounds reacted to give α-aryl derivatives in synthetically useful yields. A study of the effect of some tertiary aromatic amines and dimethyl sulfoxide, substances which complex with lead(IV), has been carried out, and in two cases the influence of bulky α- substituents has been examined.

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11

Ibrahim, Yusria R. "Synthesis of spiro(cyclohexa-diene-pyrazolo[1,5-a]pyrimidine-4-ylidene)-malononitrile derivatives." Journal of Chemical Research 2009, no. 8 (2009): 495–98. http://dx.doi.org/10.3184/030823409x466717.

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The reaction of 4-substituted aryldiazenyl-1 H-pyrazole-3,5-diamines with 7,7′,8,8′-tetra-cyanoquinodimethane gave 2-(2′,7′-diamino-6′-cyano-3′-(aryldiazenyl)-4′ H-spiro(cyclohexa[2,5]-diene-1,5′-pyrazolo[1,5- a]pyrimidine-4-ylidene) malononitriles in 63–79% yield, while, by reaction of 2-aminobenzimidazole with 7,7′,8,8′-tetracyanoquinodimethane, 2-(3′-amino-4′-cyano-6′ H-spiro-(cyclohexa[2′,5′]diene-1,5′-benzo( d)-imidazo[1,2- a]pyrimidine)-4-ylidene)malononitrile was formed in 71% yield. Rationales for these transformations are presented.

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12

Gheorghe, Viorel, Catalina Gabriela Gheorghe, Daniela Roxana Popovici, et al. "Synthesis, Purity Check, Hydrolysis and Removal of o-Chlorobenzyliden Malononitrile (CBM) by Biological Selective Media." Toxics 11, no. 8 (2023): 672. http://dx.doi.org/10.3390/toxics11080672.

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The removal yield of organic substances present in water depends on the environmental conditions, on the chemical composition of the water and on the chemical substance dissolved in the water, which constitutes the substrate of the metabolic activities of the microalgae that use these substances in the biochemical reactions of cellular enzyme complexes. o-Chlorobenzylidene malononitrile (CS, to use its military designation) was synthesized in-house, for research purposes, by a condensing reaction between o-chlorobenzaldehide and malononitrilein the presence of diethylamine. The detection, iden

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13

Al-Adiwish, Wedad M., and Wedad M. Barag. "Synthesis and Study of the Crystal Structure of 2-[(Dipyrrolidin-1-yl) methylene] malononitrile." Al-Mukhtar Journal of Sciences 37, no. 2 (2022): 105–12. http://dx.doi.org/10.54172/mjsc.v37i2.383.

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This study aims to synthesis 2-[(dipyrrolidin-1-yl)methylene] malononitrile 2 and identify its crystal structure by X-ray diffraction analysis. 2-[(dipyrrolidin-1-yl)methylene] malononitrile was prepared by a direct displacement of the methylthio group (SMe) in the 2-[bis(methylthio)methylene] malononitrile 1 with pyrrolidine as cyclic secondary amine by conjugating addition-elimination reaction under reflux conditions for two hours. The compound was obtained in high yield (80%). The structure of compound 2-[(dipyrrolidin-1-yl)methylene] malononitrile2 was identified by performing X-ray diffra

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14

Sammelson, Robert, Fariba Tayyari, Dwight Wood, and Phillip Fanwick. "Monosubstituted Malononitriles: Efficient One-Pot Reductive Alkylations of Malononitrile with Aromatic Aldehydes." Synthesis 2008, no. 2 (2008): 279–85. http://dx.doi.org/10.1055/s-2007-990945.

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15

Hammouda, M., A. S. El-Ahl, Y. M. El-Toukhee, and M. A. Metwally. "Reactions of Ketonic Mannich Bases with Malononitrile and Malononitrile dimer." Journal of Chemical Research 2002, no. 2 (2002): 89–94. http://dx.doi.org/10.3184/030823402103171258.

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The reaction of malononitrile with the tertiary Mannich base hydrochloride derived from acetophenone and some related compounds 1, 3, 5 and 7, in piperidine at 50°C afforded the pyrido[1,2-a]pyrimidine derivatives 2, tetrahydronaphthalene derivative 4 substituted quinolines 6 and benzopyran derivatives 8. While the condensation of malononitrile dimer with acetophenone, cyclohexanone and/ or α-tetralone Mannich bases hydrochloride 1, 3 and 9 gave the pyridine, isoquinoline and benzo[f]isoquinoline derivatives 10–12 in moderate to good yield.

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16

Hammouda, M., A. S. El-Ahl, Y. M. El-Toukhee, and M. A. Metwally. "Reactions of Ketonic Mannich Bases with Malononitrile and Malononitrile Dimer." ChemInform 33, no. 35 (2010): 41. http://dx.doi.org/10.1002/chin.200235041.

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17

Estrada, Leandro A., Antonio Francés-Monerris, Igor Schapiro, Massimo Olivucci, and Daniel Roca-Sanjuán. "Mechanism of excited state deactivation of indan-1-ylidene and fluoren-9-ylidene malononitriles." Physical Chemistry Chemical Physics 18, no. 48 (2016): 32786–95. http://dx.doi.org/10.1039/c6cp05231b.

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A joint experimental and computational study on the non-radiative double bond isomerisation decay channel of indan-1-ylidene malononitrile and fluoren-9-ylidene malononitrile is presented in this work.

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18

Shirotori, Mahiro, Shun Nishimura, and Kohki Ebitani. "One-pot synthesis of furfural derivatives from pentoses using solid acid and base catalysts." Catal. Sci. Technol. 4, no. 4 (2014): 971–78. http://dx.doi.org/10.1039/c3cy00980g.

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One-pot synthesis of (2-furanylmethylene)malononitrile, a Knoevenagel product of furfural with malononitrile, from xylose efficiently proceeded by combined use of acid Amberlyst-15 and acid-base Cr/hydrotalcites in 44% yield.

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19

Diyanatizadeh, Mohammad Hadi, and Issa Yavari. "Synthesis of spiro heterocyclic systems from 2-(3-oxoisobenzofuran-1(3H)-ylidene)malononitrile and binucleophiles." Journal of Chemical Research 41, no. 6 (2017): 330–32. http://dx.doi.org/10.3184/174751917x14944355549159.

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The reaction of 2-(3-oxoisobenzofuran-1(3 H)-ylidene)malononitrile, generated from phthalic anhydride and malononitrile, with different binucleophiles led to the formation of spiro heterocycles possessing a phthalide ring system in good yields.

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20

Roy, Artish, Aayushi Chanderiya, Hemlata Dangi, et al. "A one-pot multi-component synthesis of novel 2((1H-Indole-3yl) (Phenyl) methyl) malononitrile derivative by utilizing recoverable and efficient TiO2 nanocatalyst." Mediterranean Journal of Chemistry 13, no. 1 (2023): 27. http://dx.doi.org/10.13171/mjc02301231672das.

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<p>In this research, we have described a facile and user-friendly protocol for the formation of 2((1H-Indole-3yl)(Phenyl)methyl)malononitrile derivatives using a recoverable and efficient TiO2 nanocatalyst. This protocol is simple and incredibly efficient for the synthesis of novel 2((1H-Indole-3yl)(Phenyl)methyl)malononitrile derivatives. Nanoscale TiO2 is used as the catalyst. Since TiO<sub>2 </sub>has more surface area easily binds with the active site of a reactive molecule and initiates the reaction. At last, TiO<sub>2</sub> also recovered as it acts as a cat

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21

Rahmani, Fariba, and Ali Darehkordi. "Preparation of Trifluoromethylated (Arylaminomethylene)malononitriles Suitable for Synthesis of 4-Amino-2-(trifluoromethyl) quinoline Derivatives by Intramolecular Friedel–Crafts Reaction." Synthesis 50, no. 10 (2018): 2124–30. http://dx.doi.org/10.1055/s-0037-1609433.

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An approach for the synthesis of 4-amino-2-(trifluoromethyl)quinolines via the intramolecular Friedel–Crafts reaction of 2-(1-(arylamino)-2,2,2-trifluoroethylidene)malononitrile derivatives is reported. This simple protocol provides a wide variety of 4-amino-2-(trifluoromethyl)quinolines in good to excellent yields, without any purification. Furthermore, the 2-(1-(arylamino)-2,2,2-trifluoroethylidene) malononitrile derivatives used in this project have been synthesized by the reaction of N-aryl-2,2,2-trifluoroacetimidoyl chlorides and malononitrile at ambient temperature and under microwave ir

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22

Lozinski, Oleg, Tatyana Shokol, Oleg Shishkin, Vladimir Medvediev, and Vladimir Khilya. "The redeeming features of reaction of the 8-formyl-7-hydroxychromones with malononitrile." French-Ukrainian Journal of Chemistry 2, no. 1 (2014): 10–15. http://dx.doi.org/10.17721/fujcv2i1p10-15.

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A range of 4H,8H-pyrano[2,3-f]chromen-4,8-diones have been prepared using Knoevenagel reaction of the 8-formyl-7-hydroxychromones with malononitrile. The 4H,8H-pyrano[2,3-f]chromen-4,8-dione derivative was also obtained through the acid hydrolysis of the 8-imino-4H,8H-pyrano[2,3-f]chromen-4-one. 8-Formyl-7-hydroxychromone 1 was found to add two molecules of malononitrile through Michael addition resulting in formation of the 2-[8-amino-3-(4-chlorophenyl)-9-cyano-2-methyl-4-oxo-4H,10H-pyrano[2,3-f]chromen-10-yl]malononitrile.

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23

Kalogirou, Andreas S., and Panayiotis A. Koutentis. "(Z)-2-{[(4-Chloro-5H-1,2,3-dithiazol-5-ylidene)amino](methylthio)methylene}malononitrile." Molbank 2022, no. 1 (2022): M1354. http://dx.doi.org/10.3390/m1354.

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Reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with 2-[amino(methylthio)methylene])malononitrile (1 equiv) in the presence of pyridine (2 equiv) gave (Z)-2-{[(4-chloro-5H-1,2,3-dithiazol-5-ylidene)amino](methylthio)methylene}malononitrile in 20% yield. The compound was fully characterized.

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24

Ansari, K. R., M. A. Quraishi, Ambrish Singh, Sowmya Ramkumar, and Ime B. Obote. "Corrosion inhibition of N80 steel in 15% HCl by pyrazolone derivatives: electrochemical, surface and quantum chemical studies." RSC Advances 6, no. 29 (2016): 24130–41. http://dx.doi.org/10.1039/c5ra25441h.

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The corrosion protection of N80 steel in 15% HCl using 2-(3-amino-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)(p-tolyl)methyl)malononitrile (PZ-1) and 2-((3-amino-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)(phenyl)methyl)malononitrile (PZ-2) has been investigated.

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25

Chang, Ming-Jen, Tzu-Chien Fang, Hsing-Yang Tsai, Ming-Hui Luo, and Kew-Yu Chen. "2-(4-Nitrobenzylidene)malononitrile." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (2012): o957. http://dx.doi.org/10.1107/s1600536812008896.

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In the title compound, C10H5N3O2, the benzylidenemalononitrile unit is nearly planar, with a maximum deviation of 0.129 (2) Å for a terminal N atom; the nitro group is approximately coplanar with the benzene ring [dihedral angle = 8.8 (3)°]. An intramolecular C—H...N hydrogen bond stabilizes the molecular conformation.

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26

Helmchen, Günter, Sebastian Förster, and Olena Tverskoy. "Malononitrile as Acylanion Equivalent." Synlett 2008, no. 18 (2008): 2803–6. http://dx.doi.org/10.1055/s-0028-1083540.

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27

Nesterov, Vladimir N., Elena A. Viltchinskaia, and Svitlana V. Nesterova. "[(2-Methoxyanilino)methylene]malononitrile." Acta Crystallographica Section E Structure Reports Online 59, no. 5 (2003): o625—o627. http://dx.doi.org/10.1107/s1600536803007293.

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28

Podda, Enrico, Massimiliano Arca, Anna Pintus, et al. "2-(2,7-Bis(pyridin-3-ylethynyl)fluoren-9-ylidene)malononitrile." Molbank 2023, no. 2 (2023): M1619. http://dx.doi.org/10.3390/m1619.

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The 2-(2,7-bis(pyridin-3-ylethynyl)fluoren-9-ylidene)malononitrile (1) was synthesized by reaction of 2,7-bis(pyridin-3-ylethynyl)fluoren-9-one with malononitrile in DMSO solution. The structural characterization of 1 by SC-XRD analysis was accompanied by elemental analysis, FT-IR, NMR, and MS measurements.

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29

Purba, WT, PS Roy, S. Jannat, SA Begum, and MM Rahman. "Microwave-assisted urea catalyzed Knoevenagel condensation of aldehydes with active methylene compounds." Bangladesh Journal of Scientific and Industrial Research 55, no. 2 (2020): 159–64. http://dx.doi.org/10.3329/bjsir.v55i2.47637.

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Rapid and efficient method for the synthesis of substituted olefins such as 2-(4-chlorophenylmethylene) malononitrile, 2-(4-hydroxyphenylmethylene) malononitrile and 2-cyano-3-(4-hydroxyphenyl) acrylamide etc under the influence of microwave irradiation are described. Urea has been utilized as an efficient catalyst for the Knoevenagel condensation of aldehydes with acidic active methylene compounds such as malononitrile, ethylcyanoacetate and cyanoacetamide to afford substituted olefins under the influence of microwave irradiation. The reaction proceeds smoothly under mild and solvent free con

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30

Kalogirou, Andreas S., Andreas Kourtellaris, and Panayiotis A. Koutentis. "2-[3,5-Bis(5-bromothien-2-yl)-4H-1,2,6-thiadiazin-4-ylidene]-malononitrile." Molbank 2025, no. 1 (2025): M1977. https://doi.org/10.3390/m1977.

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Bromination of 2-[3,5-di(thien-2-yl)-4H-1,2,6-thiadiazin-4-ylidene]-malononitrile with N-bromosuccinimide in THF, at ca. 20 °C for 24 h gave 2-[3,5-bis(5-bromothien-2-yl)-4H-1,2,6-thiadiazin-4-ylidene]-malononitrile in 82% yield. The latter is intended as a scaffold for preparing donors for organic photovoltaics.

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31

Macleod, JK, and TF Molinski. "Synthetic Studies on Wedeligenin: Preparation of 3-Hydroxy-Substituted Decalincarbonitriles as a Model for 'A Ring' Annulation." Australian Journal of Chemistry 43, no. 8 (1990): 1309. http://dx.doi.org/10.1071/ch9901309.

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Six new 3-hydroxydecalincarbonitriles were synthesized by employing an annulation strategy involving intramolecular alkylation of 5-bromoalkyl substituted malononitriles or acetonitriles. 2-Allyl-2-methylcyclohexanone was condensed with malononitrile to give the dialkylcyclohexylidenepropanedinitrile (14). Alternatively, Horner-Emmons- Wittig condensation of the same ketone with diethyl cyanomethylphosphonate gave the corresponding acetonitrile (28). Reduction of the dinitrile with sodium borohydride to give a mixture of cis and trans cyclohexyl malononitriles followed by epoxidation of the al

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32

Zhang, Xinying, Xiaoyan Li, Xuesen Fan, Xia Wang, Jianji Wang, and Guirong Qu. "Controllable Synthesis of Pyrazolo[3,4-b]pyridines or Substituted Malononitrile Derivatives through Multi-Component Reactions in Ionic Liquid." Australian Journal of Chemistry 62, no. 4 (2009): 382. http://dx.doi.org/10.1071/ch08290.

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A multi-component reaction of aldehyde, malononitrile, and 5-amino-3-methyl-1-phenylpyrazole was carried out smoothly in [bmim][BF4] without any added catalyst. Through this reaction, pyrazolo[3,4-b]pyridines or substituted malononitrile derivatives were obtained conveniently and controllably at different temperatures. The ionic liquid used can be easily recovered and efficiently reused for at least five runs.

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33

Bankuru, Jyothi, Venkateswara Rao Battula, Himabindu Gandham, S. Tirumala Santhoshkumar, and Devi Lagudu. "ENHANCING REACTION EFFICIENCY IN THE GREEN PREPARATION OF 2-(2-OXOINDOLIN-3- YLIDENE)MALONONITRILES WITH ULTRASOUNDASSISTED KNOEVENAGEL CONDENSATION." RASAYAN Journal of Chemistry 17, no. 04 (2024): 1454–59. http://dx.doi.org/10.31788/rjc.2024.1748842.

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The development of 2-(2-oxoindolin-3-ylidene)malononitrile analogs has been quantitatively reported using an exceedingly feasible green methodology. This protocol involves the Knoevenagel condensation of various isatins and indeno[1,2-b]quinoxalin-11-nones with malononitrile in a solvent of EtOH under ultrasonic irradiation. This method significantly enhances the reaction efficiency, offering enormous yields ranging from 80% to 96% for the target products within a remarkably short reaction time of 10 to 15 minutes at ambient temperature. The synthesized 2-(2-oxoindolin-3-ylidene)malononitrile

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34

Helmy, Ahlam M. A., Mohamed A. Morsi, and Mohamed H. Elnagdi. "Structure of the Products of Coupling of Substituted Ethylidene Malononitrile with Aryldiazonium Salts: Polarographic and Acid Dissociation Measurements." Collection of Czechoslovak Chemical Communications 59, no. 8 (1994): 1752–60. http://dx.doi.org/10.1135/cccc19941752.

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The structure of products of coupling of (α-ethoxycarbonyl-β-amino)ethylidene malononitrile (Ia) and (α-cyano-β-amino)ethylidene malononitrile (Ib) with aromatic diazonium salts could be established to be the corresponding hydrazone IIa (α-ethoxycarbonyl-α-phenylhydrazono-β-amino)ethylidene malononitrile and IIb (α-cyano-α-p-bromophenylhydrazono-β-amino)ethylidene malononitrile, via inspection of acid dissociation constants and the electrochemical behaviour of these products. IIa and IIb showed pKa ≈ 6 which is comparable to that of 2-phenylhydrazono-3-iminobutyronitrile (IV). The polarograms

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35

Lipin, Konstantin V. "SEMI-INDUSTRIAL TECHNOLOGY FOR SYNTHESIS OF 2-(1,3-DITHIOLAN-2-YLIDENE) MALONONITRILE." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 63, no. 4 (2020): 68–73. http://dx.doi.org/10.6060/ivkkt.20206304.6124.

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This article analyzes the developments of the scientific team of the Chemical and Pharmaceutical Faculty of Chuvash State University I.N. Ulyanov in the field of synthesis of 1,3-dithioheterocycles and based on them a method of synthesis of 2-(1,3-dithiolane-2-ylidene) malononitrile suitable for scaling was developed. The basis was chosen for the well-known three-component synthesis method, which has several disadvantages: the use of toxic and inaccessible reagents, multi-stage. During laboratory testing, this method of synthesis was improved. The developed method for producing 2-(1,3-dithiola

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36

Mojtahedi, Mohammad M., Masoomeh Mehraban, Kiana Darvishi, and M. Saeed Abaee. "Ultrasound mediated synthesis of dihydropyrano[3,2-d][1,3]dioxin-7-carbonitrile derivatives in H2O/EtOH medium." Heterocyclic Communications 23, no. 2 (2017): 91–95. http://dx.doi.org/10.1515/hc-2017-0014.

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AbstractA one-pot cyclocondensation of 1,3-dioxane-5-one (1) with malononitrile and aromatic aldehydes in aqueous sodium hydroxide under ultrasonic irradiation furnishes a series of pyrano[3,2-d][1,3]dioxin derivatives 3. Reactions are completed after a few minutes and the precipitated products are purified by simple crystallization from ethanol. The reaction with ethyl cyanoacetate instead of malononitrile gives the respective analogous products in high yields.

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37

Enders, Dieter, Kun Zhao, Ying Zhi, and Ai Wang. "Synthesis of Malononitrile-Substituted Diarylmethines via 1,6-Addition of Masked Acyl Cyanides to para-Quinone Methides." Synthesis 50, no. 04 (2017): 872–80. http://dx.doi.org/10.1055/s-0036-1590947.

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An efficient method for the synthesis of malononitrile-substituted diarylmethines through 1,6-conjugate addition of para-quinone methides with masked acyl cyanide (MAC) reagents has been developed. Under mild conditions, the scalable reaction occurs in good to excellent yields providing a straightforward access to a series of malononitrile-substituted diarylmethines. The synthetic utility of this protocol has been demonstrated in the synthesis of bioactive compounds.

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38

Chen, Jialuo, Lili Duan, Kunming Liu, and Jin-Biao Liu. "A Convenient Synthesis towards 2-Bromo-2-(methoxy(phenyl)methyl)malononitrile and 2-Iodo-2-(methoxy(phenyl)methyl)malononitrile." Molbank 2022, no. 2 (2022): M1373. http://dx.doi.org/10.3390/m1373.

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This short note elaborates a concise protocol for the synthesis of two novel vicinal haloethers bearing a malonontrile group, 2-bromo-2-(methoxy(phenyl)methyl)malononitrile (1) and 2-iodo-2-(methoxy(phenyl)methyl)malononitrile (2). The structures of the synthesized compounds were confirmed by 1H, 13C-NMR spectroscopy. The final products indicate that methanol not only acts as solvent but also participates in and dominates the reaction result.

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39

Varenichenko, S. A., A. V. Kovtun, V. K. Farat, and O. K. Farat. "An efficient synthetic route to substituted xanthene analogues." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 3 (June 2025): 100–106. https://doi.org/10.32434/0321-4095-2025-160-3-100-106.

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The reactions of N-[(9-chloro-1,2-dihydrocyclopenta[b]chromen-3-yl)methylene]-N-methylmethanaminium and N-[(11-chloro-7,8,9,10-tetrahydrocyclohepta[b]chromen-6-yl)methylene]-N-methylmethanaminium perchlorates with (1-phenylethylidene)malononitrile were studied in boiling acetonitrile in the presence of piperidine. These reactions led to the formation of new organic dyes, [(2E)-1-phenyl-3-(9-piperidin-1-yl-1,2-dihydrocyclopenta[b]chromen-3-yl)prop-2-en-1-ylidene]malononitrile and [(2E)-1-phenyl-3-(11-piperidin-1-yl-7,8,9,10-tetrahydrocyclohepta[b]chromen-6-yl)prop-2-en-1-ylidene]malononitrile,

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40

Motiyenko, R. A., I. A. Armieieva, L. Margulès, E. A. Alekseev, and J. C. Guillemin. "Rotational spectroscopy of malononitrile and its corresponding monoisocyanide isomer, isocyanoacetonitrile." Astronomy & Astrophysics 623 (March 2019): A162. http://dx.doi.org/10.1051/0004-6361/201834587.

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Context. Nitriles constitute almost 20% of the molecules observed in the interstellar medium, whereas only one dinitrile and one isocyanonitrile compound have been detected up to now. The lack of detections of such compounds may be partially explained by the lack of accurate spectroscopic data on their rotational spectra.Aims. Two small seven-atom dinitriles, malononitrile NCCH2CN and isocyanoacetonitrile NCCH2NC, were chosen as target species for this study. For malononitrile the goal of the study is to systematize all the previous measurements, and to extend the measurements to the sub-milli

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41

Jing, Yi, and Luo-Ting Yu. "2-[4-(Diethylamino)benzylidene]malononitrile." Acta Crystallographica Section E Structure Reports Online 67, no. 6 (2011): o1556. http://dx.doi.org/10.1107/s1600536811019295.

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42

Svintsitskaya, N. I., A. V. Aleksandrova, A. V. Dogadina, and B. I. Ionin. "Reaction of aminoethynylphosphonates with malononitrile." Russian Journal of General Chemistry 77, no. 5 (2007): 963–64. http://dx.doi.org/10.1134/s107036320705026x.

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43

Wasiutynski, T., W. Olejarczyk, J. Sciesinski, and W. Witko. "Phase transition studies of malononitrile." Journal of Physics C: Solid State Physics 20, no. 5 (1987): L65—L69. http://dx.doi.org/10.1088/0022-3719/20/5/002.

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44

Kang, Tai-Ran, and Lian-Mei Chen. "(E)-2-(1,3-Diphenylallylidene)malononitrile." Acta Crystallographica Section E Structure Reports Online 65, no. 12 (2009): o3164. http://dx.doi.org/10.1107/s1600536809048338.

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45

Soltzberg, L. J., Michele M. Boucher, Susan D. Bromley, et al. "Ferroelasticity in malononitrile thin films." Ferroelectrics 89, no. 1 (1989): 7–15. http://dx.doi.org/10.1080/00150198908017879.

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46

Gan, Hai-feng, Xue-wei Liu, Zheng Fang, and Kai Guo. "2-[4-(Benzyloxy)benzylidene]malononitrile." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (2012): o1690. http://dx.doi.org/10.1107/s1600536812020053.

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In the title molecule, C17H12N2O, the dihedral angle between the two benzene rings is 84.98 (10)°. The dicyanoethylene group is coplanar with the benzene ring to which it is bonded. No classic hydrogen bonds were found in the crystal.

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47

Samet, A. V., N. B. Chernysheva, A. M. Shestopalov, and V. V. Semenov. "Interaction of levoglucosenone with malononitrile." Russian Chemical Bulletin 48, no. 1 (1999): 210–12. http://dx.doi.org/10.1007/bf02494434.

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48

Brvar, M. "Chlorobenzylidene malononitrile tear gas exposure." Human & Experimental Toxicology 35, no. 2 (2015): 213–18. http://dx.doi.org/10.1177/0960327115578866.

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Objective: Chlorobenzylidene malononitrile (CS) is the tear gas used by the police. The aim was to evaluate an amphoteric, hypertonic, and chelating rinsing solution in CS exposure. Methods: The first (CS) group of six police officers was exposed to CS only. The second (preexposure) group of eight sprayed their faces with an aqueous, hypertonic, amphoteric, and chelating solution before CS exposure. The third (postexposure) group of eight sprayed their faces with an aqueous, hypertonic, amphoteric, and chelating solution after CS exposure. The time between exiting the CS cloud and arriving at

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49

Yurow, H. "Novel fluorescence reaction for malononitrile." Talanta 33, no. 12 (1986): 1039–40. http://dx.doi.org/10.1016/0039-9140(86)80248-x.

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50

Lu, Yin-Xiang, Hui Zhou, Peng Guo, Lan Jin, and Wei Xu. "Structure of 2-(1-phenylimidiazolidin-2-ylidene)- malononitrile and 2-(hexahydropyrimidinyl-2-ylidene)- malononitrile." Journal of Chemical Crystallography 36, no. 10 (2006): 691–95. http://dx.doi.org/10.1007/s10870-006-9120-6.

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