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Journal articles on the topic 'Malononitrile'

Author: Grafiati

Published: 4 June 2021

Last updated: 2 February 2022

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1

Zanardi, Franca, Claudio Curti, Andrea Sartori, and Lucia Battistini. "Exploring the Remote Reactivity of π-Extended Carbonyl Compounds: The Vinylogous Alkylidene Malononitrile Activation Strategy." Synlett 29, no. 03 (November 15, 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 and selectively. Merging the vinylogy concept with the malononitrile HOMO-raising activation strategy and complementary organocatalytic activation modalities (i.e. LUMO-lowering iminium ion activation) turned out to be a successful option, as demonstrated by the number of diverse carbocyclic and heterocyclic chiral products that were (stereo)selectively accessed through this chemistry.1 Introduction2 Reactions of Cyclohexenylidene Malononitriles with Enals3 Reactions of Allylidene Malononitriles with Enals4 Reactions of Indolylmethylene Malononitriles with Enals5 Conclusion

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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 (May 1, 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 (November 14, 2019): 32. http://dx.doi.org/10.3390/ecsoc-23-06524.

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5

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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6

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

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7

Kozyrod, RP, J. Morgan, and JT Pinhey. "The C-Arylation of α-Cyano Esters and Malononitriles by Aryllead(IV) Triacetates." Australian Journal of Chemistry 44, no. 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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8

Ibrahim, Yusria R. "Synthesis of spiro(cyclohexa-diene-pyrazolo[1,5-a]pyrimidine-4-ylidene)-malononitrile derivatives." Journal of Chemical Research 2009, no. 8 (August 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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9

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 (January 2008): 279–85. http://dx.doi.org/10.1055/s-2007-990945.

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10

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 (February 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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11

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 (May 20, 2010): 41. http://dx.doi.org/10.1002/chin.200235041.

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12

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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13

Nesterov, Vladimir N., Elena A. Viltchinskaia, and Svitlana V. Nesterova. "[(2-Methoxyanilino)methylene]malononitrile." Acta Crystallographica Section E Structure Reports Online 59, no. 5 (April 16, 2003): o625—o627. http://dx.doi.org/10.1107/s1600536803007293.

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14

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 (March 3, 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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15

Helmchen, Günter, Sebastian Förster, and Olena Tverskoy. "Malononitrile as Acylanion Equivalent." Synlett 2008, no. 18 (October 15, 2008): 2803–6. http://dx.doi.org/10.1055/s-0028-1083540.

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16

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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17

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 (June 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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18

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 (March 28, 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 irradiation in excellent yields, for the first time.

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19

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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20

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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21

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 allyl substituent, gave a separable mixture of four epoxides, two of which, (17) and (19), were site-selectively ring-opened to the bromohydrins. Each bromohydrin was quantitatively converted into its respective O- trimethylsilyl bromohydrin ether and cyclized to afford the respective decalindicarbonitriles (6) and (7). The substituted acetonitrile (28) was reduced to a 5 : 2 mixture of the corresponding cyclohexylacetonitriles with magnesium in methanol and the products were carried through to their respective O- trimethylsilyl bromohydrin ethers and cyclized to afford decalincarbonitriles (8)-(11). The structure and stereochemistry of the new decalins were assigned by 1H and 13C n.m.r. spectroscopy.

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22

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 (June 16, 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 conditions and the products are obtained in good yield. The method is applicable for a wide range of aldehydes including aromatic and heterocyclic substrates. Bangladesh J. Sci. Ind. Res.55(2), 159-164, 2020

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23

Jing, Yi, and Luo-Ting Yu. "2-[4-(Diethylamino)benzylidene]malononitrile." Acta Crystallographica Section E Structure Reports Online 67, no. 6 (May 28, 2011): o1556. http://dx.doi.org/10.1107/s1600536811019295.

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24

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 (May 2007): 963–64. http://dx.doi.org/10.1134/s107036320705026x.

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25

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

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26

Soltzberg, L. J., Michele M. Boucher, Susan D. Bromley, Dawn M. Crane, Karen M. Durgin, Cheryl A. Howley, Angela A. Spalaris, Gretchen B. Swenson, and Anne Marie Yasi. "Ferroelasticity in malononitrile thin films." Ferroelectrics 89, no. 1 (January 1989): 7–15. http://dx.doi.org/10.1080/00150198908017879.

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27

Kang, Tai-Ran, and Lian-Mei Chen. "(E)-2-(1,3-Diphenylallylidene)malononitrile." Acta Crystallographica Section E Structure Reports Online 65, no. 12 (November 21, 2009): o3164. http://dx.doi.org/10.1107/s1600536809048338.

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28

Brvar, M. "Chlorobenzylidene malononitrile tear gas exposure." Human & Experimental Toxicology 35, no. 2 (March 24, 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 the “ready for action” checkpoint was measured. Their facial pain both inside the CS cloud and at the checkpoint was assessed (0–10 points). Results: The pain level inside the CS cloud was significantly lower in the preexposed group (5.6 ± 1.1; p = 0.01) than in the CS group (9.7 ± 0.5) and in the postexposure group (9.1 ± 0.4) where it was similar. The time interval between CS exposure and arrival at the checkpoint in the preexposure group (1:26 ± 0:44 min) was significantly shorter than both in the CS group (2:28 ± 0:25 min; p = 0.04) and postexposure group (2:30 ± 0:48 min; p = 0.02) where it was not different. The residual pain at the checkpoint in the preexposure (1.1 ± 0.4) and postexposure (1.4 ± 0.7) groups was similar with a significant lower pain level than in the CS group (2.3 ± 0.5; p = 0.02). Conclusion: CS decontamination with an aqueous, hypertonic, amphoteric, and chelating solution reduces facial pain, whereas prevention with it reduces pain and recovery time.

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29

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 (May 12, 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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30

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

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31

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

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32

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 (August 2, 2006): 691–95. http://dx.doi.org/10.1007/s10870-006-9120-6.

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33

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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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 were found to be similar and consisted mainly of 4e reduction wave characteristic for hydrazones; also similar to the model hydrazone IV. The behaviour of 1-(p-methoxyphenyl)-3,5-dicyano-4-amino-6-iminopyridazine (IIIb) was found to be totally different. It did not reveal any potentiometrically traceable ionization step in aqueous media. Moreover its polarograms were totally different and consisted of two 2e waves. The more positive was E1/2-pH dependent and the more negative was E1/2-pH independent. Both waves were assigned for saturation of exocyclic and endocyclic C=N linkage. The mechanism of the electrode processes is also discussed.

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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 (April 17, 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-dithiolane-2-ylidene)malononitrile consists of reacting malononitrile with carbon disulfide in the presence of potassium carbonate, adding dichloroethane to the resulting mixture, and boiling the mixture for 10-15 min. The final compound is isolated by diluting the reaction mass with water. Based on the developed method, a technological scheme for the synthesis of 2- (1,3-dithiolane-2-ylidene)malononitrile was compiled. The selected production method consists of four technological operations: mixing the starting components in the reactor, heating and boiling the reaction mixture, diluting the reaction mass with water and crystallizing the product, filtering 2-(1,3-dithiolane-2-ylidene)malononitrile. The first three stages can be carried out in one technological equipment - a reactor equipped with a stirrer and a jacket. For filtering it is necessary to use a nutsche filter. Based on the developed methodology, a technological scheme has been created, its description has been compiled. The design process capacity is 5 kg/h of 2-(1,3-dithiolane-2-ylidene)malononitrile. The necessary equipment is calculated. A standard mixing reactor with a volume of 0.1 m3 and a nutsche filter NFP-0.25-630 PP were selected. To mix the reaction mass, the reactor should be equipped with an anchor type mixer. The developed technology compares favorably with the use of simple and cheap raw materials common in the chemical industry, the short synthesis time and the use of standard technological equipment.

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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 (April 1, 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 (November 23, 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

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-millimeter wavelength range. The spectrum of isocyanoacetonitrile has not been studied before.Methods. The rotational spectra of the two molecules were measured in the frequency range 150–660 GHz using the Lille fast-scan spectrometer. The spectroscopic study was supported by high-level theoretical calculations on the structure of these molecules and their harmonic force field.Results. Accurate frequency predictions for malononitrile and isocyanoacetonitrile were calculated on the basis of the analysis of their rotational spectra. The influence of the spin statistics on the intensities of the lines of malononitrile was taken into account. The provided line lists and sets of molecular parameters meet the needs of astrophysical searches for the two molecules.

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39

Koutentis, Panayiotis A., and Charles W. Rees. "Reaction of Herz salts with malononitrile: a general route to (6H-1,2,3-benzodithiazol-6-ylidene)malononitriles." Journal of the Chemical Society, Perkin Transactions 1, no. 3 (January 3, 2002): 315–19. http://dx.doi.org/10.1039/b110024f.

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40

El-mahdy, Kamelia, Azza El-Kazak, Mohamed Abdel-Megid, Magdy Seada, and Osama Farouk. "Synthesis, Characterization and Biological Evaluation of some New Thieno[2,3-d]Pyrimidine Derivatives." JOURNAL OF ADVANCES IN CHEMISTRY 5, no. 1 (April 29, 2009): 581–91. http://dx.doi.org/10.24297/jac.v5i1.937.

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10-Oxo-4,6,7,8,9,10-hexahydroprazolo[1,5-a][1]benzothieno[2,3-d]pyrimidine-3-carbaldehyde (2) was prepared by Vilsmeier-Haack reaction of 3-amino-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one (1). Reaction of carbaldehyde derivative 2 with malononitrile afforded arylidene malononitrile 3. Cyclization of the latter compound with thiourea yielded pyrimidinethione 4. Interaction of carbaldehyde derivative 2 in presence of thiourea with keto- compounds such as ethyl acetoacetate, or acetylacetone, or dimedone or ethyl cyanoacetate gave pyrimidine derivatives 5-8. Hydrazinolysis of carbaldehyde derivative 2 gave the hydrazone 9. Reaction of the latter with phenyl isothiocyanate afforded thiosemicarbazone 10, which underwent cyclization with oxalyl chloride to give thioxoimidazolidinedione 11. Condensation of compound 2 with thiosemicarbazide furnished thiosemicarbazone derivative 12. Reaction of compound 2 with aminopyrazolone in the presence of an acid and/or a base afforded pyrazolones 13 and 14. Treatment of carbaldehyde derivative 2 with cyanoacetohydrazide gave acrylohydrazide 15. Interaction of the latter with carbon disulfide yielded mercaptooxadiazole 16. Condensation of compound 2 with acetylpyridazinone 17 produced chalcone 18. Reaction of compound 18 with malononitrile in pyridine gave cyanopyran 19, while its reaction with malononitrile in presence of ammonium acetate in ethanol yielded cyanopyridine 20. Structures of the newly synthesized products have been deduced on the basis of elemental analysis and spectral data. The synthesized compounds were screened for their antimicrobial activity.

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41

Guo, Zhiqian, Andong Shao, and Wei-Hong Zhu. "Long wavelength AIEgen of quinoline-malononitrile." Journal of Materials Chemistry C 4, no. 14 (2016): 2640–46. http://dx.doi.org/10.1039/c5tc03369a.

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In this Highlight, we summarize some recent advances in the area of red to near-infrared fluorescent AIE-active organic materials via tailoring the building block of quinoline-malononitrile (QM), and its application in bioimaging.

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42

Vanmaele, Luc J. "New dyes derived from malononitrile dimer." Tetrahedron Letters 33, no. 7 (February 1992): 961–64. http://dx.doi.org/10.1016/s0040-4039(00)91588-0.

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43

Schickinger, Manuel, Yvonne Morgenstern, Karin Stierstorfer, and Andreas Kornath. "Protonation of Malononitrile in Superacidic Solutions." Zeitschrift für anorganische und allgemeine Chemie 643, no. 21 (August 2, 2017): 1431–35. http://dx.doi.org/10.1002/zaac.201700220.

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44

Laxer, Avital, and Bilha Fischer. "A facile synthesis of (15N2) malononitrile." Journal of Labelled Compounds and Radiopharmaceuticals 43, no. 1 (January 2000): 47–53. http://dx.doi.org/10.1002/(sici)1099-1344(200001)43:1<47::aid-jlcr289>3.0.co;2-k.

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45

Han, Lu-Na, Min Zhang, Ran-Zhe Lu, Wen-Bin Wei, and Hai-Bo Wang. "2-[2-(4-Nitrophenyl)hydrazinylidene]malononitrile." Acta Crystallographica Section E Structure Reports Online 66, no. 1 (December 19, 2009): o196. http://dx.doi.org/10.1107/s1600536809053136.

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46

Feng, Xiao-Zhong, Fu-Feng Yan, and Zhen-Ping Li. "2-(1,3-Dibenzylimidazolidin-2-ylidene)malononitrile." Acta Crystallographica Section E Structure Reports Online 64, no. 6 (May 21, 2008): o1120. http://dx.doi.org/10.1107/s1600536808014025.

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47

Tkach, I. I., A. V. Reznichenko, and E. A. Luk'yanets. "Reaction of 4-diethylaminosalicylaldehyde with malononitrile." Chemistry of Heterocyclic Compounds 28, no. 8 (August 1992): 872–80. http://dx.doi.org/10.1007/bf00531317.

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48

Ettenger, George B., Brian Wesley Williams, Daniel Brillhart, and Margaret E. Kastner. "2-(1,2,3,4-Tetrahydrophenanthren-1-ylidene)malononitrile." Acta Crystallographica Section E Structure Reports Online 65, no. 7 (June 27, 2009): o1711. http://dx.doi.org/10.1107/s1600536809023988.

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49

Dotsenko, V. V., A. V. Bespalov, A. A. Russkikh, V. K. Kindop, N. A. Aksenov, I. V. Aksenova, S. V. Shcherbakov, and S. N. Ovcharov. "Reactions of Malononitrile Dimer with Isothiocyanates." Russian Journal of General Chemistry 91, no. 6 (June 2021): 951–65. http://dx.doi.org/10.1134/s1070363221060013.

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Abstract The reaction of 2-amino-1,1,3-tricyanopropene (malononitrile dimer) with isothiocyanates leads to 1-substituted 4,6-diamino-2-thioxo-1,2-dihydropyridine-3,5-dicarbonitriles or 4,6-diamino-2-(phenylimino)-2H-thiopyran-3,5-dicarbonitrile, depending on the conditions. Quantum-chemical modeling of the IR spectra and reaction routes for the synthesized compounds was carried out. In silico predictive analysis of potential protein targets, compliance with bioavailability criteria, and ADMET parameters was performed.

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50

Sharma, Dinesh, and Jagdish Makrandi. "Iodine mediated one-pot synthesis of 3-cyano and 3-cyano-4-methylcoumarins." Journal of the Serbian Chemical Society 79, no. 5 (2014): 527–31. http://dx.doi.org/10.2298/jsc130127140s.

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2-Hydroxybenzaldehydes 1a-e on reaction with malononitrile 2 in the presence of iodine as catalyst give 3-cyanocoumarins 3a-e in one step under thermal heating as well as microwave irradiations. The latter conditions are much more efficient in terms of time (2-5 minutes) and yield as compared to thermal conditions (2-2.5 hours). Following similar procedure, 3-cyano-4-methylcoumarins 3f-i have also been prepared by the reaction of 2-hydroxyacetophenones 1f-i with malononitrile 2.

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