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Journal articles on the topic 'Enaminone synthesis'

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Author: Grafiati

Published: 11 March 2023

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1

Chattopadhyay, Amit Kumar, and Stephen Hanessian. "Cyclic enaminones. Part II: applications as versatile intermediates in alkaloid synthesis." Chemical Communications 51, no. 92 (2015): 16450–67. http://dx.doi.org/10.1039/c5cc05892a.

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Among many other strategies, the enaminone approach is an important strategy to construct and diversify the azacyclic core in various alkaloids syntheses. In this brief review we discuss the application of cyclic enaminones as building blocks, as well as potential intermediates in the total synthesis of selected alkaloids.

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2

Štanfel, Urša, Dejan Slapšak, Uroš Grošelj, Franc Požgan, Bogdan Štefane, and Jurij Svete. "Synthesis of 6,7-Dihydro-1H,5H-pyrazolo[1,2-a]pyrazoles by Azomethine Imine-Alkyne Cycloadditions Using Immobilized Cu(II)-Catalysts." Molecules 26, no. 2 (January 13, 2021): 400. http://dx.doi.org/10.3390/molecules26020400.

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A series of 12 silica gel-bound enaminones and their Cu(II) complexes were prepared and tested for their suitability as heterogeneous catalysts in azomethine imine-alkyne cycloadditions (CuAIAC). Immobilized Cu(II)–enaminone complexes showed promising catalytic activity in the CuAIAC reaction, but these new catalysts suffered from poor reusability. This was not due to the decoordination of copper ions, as the use of enaminone ligands with additional complexation sites resulted in negligible improvement. On the other hand, reusability was improved by the use of 4-aminobenzoic acid linker, attached to 3-aminopropyl silica gel via an amide bond to the enaminone over the more hydrolytically stable N-arylenamine C-N bond. The study showed that silica gel-bound Cu(II)–enaminone complexes are readily available and suitable heterogeneous catalysts for the synthesis of 6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazoles.

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3

Masaret, Ghada S., and Thoraya A. Farghaly. "Synthesis of 8,10-disubstituted-triazoloperimidines from (E)-3-(dimethylamino)-1-(8- phenyl-8H-[1,2,4]triazolo[4,3-a]perimidin-10-yl)prop-2-en-1-one and Their Antimicrobial Activity." Current Organic Synthesis 15, no. 1 (March 20, 2018): 126–36. http://dx.doi.org/10.2174/1570179414666170601121137.

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Aim and Objective: Enaminones belay to be extremely stable compounds and constitute a versatile group of salutary precursors for the synthesis of enormous classes of organic compounds. So, in this context, we synthesized a new enaminone, namely, (E)-3-(dimethylamino)-1-(8-phenyl-8H-[1,2,4]triazolo[4,3- a]perimidin-10-yl)prop-2-en-1-one (enaminone 2). Materials and Methods: The reaction of enaminone 2 with different types of hydrazonoyl chlorides or hydrazine hydrate afforded new substituted pyrazoles. Also, the reaction of enaminone with 6-amino-2- thioxopyrimidin-4-one in acetic acid under reflux produced 2-thioxopyridopyrimidinone derivative. The latter thione derivative reacts with hydrazonoyl chlorides to give pyridotriazolopyrimidines. 5-(8-Phenyl-8H- [1,2,4]triazolo[4,3-a]perimidin-10-yl)isoxazole was produced from the reaction of enaminone 2 with hydroxylamine. Results & Conclusion: The structure of all the novel perimidine derivatives was confirmed on the basis of spectral data and elemental analyses. The enaminone and the newly synthesized compounds were tested for their antimicrobial activity, and the results obtained revealed that some derivatives are more potent than the reference drugs used.

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4

Ciber, Luka, Franc Požgan, Helena Brodnik, Bogdan Štefane, Jurij Svete, and Uroš Grošelj. "Synthesis and Catalytic Activity of Organocatalysts Based on Enaminone and Benzenediamine Hydrogen Bond Donors." Catalysts 12, no. 10 (September 28, 2022): 1132. http://dx.doi.org/10.3390/catal12101132.

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A total of 24 novel organocatalysts based on (S)-quininamine as a chiral tertiary amine and on enaminone or 1,2-benzenediamine as hydrogen bond donors were synthesized. The enaminone-type catalysts were prepared by the transamination of N,N-dimethyl enaminones with (S)-quininamine (9 examples) and the 1,2-benzenediamine-type catalysts were prepared in 3 steps from (S)-quininamine and ortho-fluoronitrobenzene derivatives (15 examples). Their organocatalytic activity was evaluated in the Michael addition of acetylacetone to trans-β-nitrostyrene. Enantioselectivities of up to 72% ee were observed.

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5

Agamy, Samia Michel, Mervat Mohammed Abdel-Khalik, Mona Hassan Mohamed, and Mohammed Hilmy Elnagdi. "Enaminones as Building Blocks In Heterocyclic Synthesis: A New One Pot Synthesis of Polyfunctional Substituted Pyridines." Zeitschrift für Naturforschung B 56, no. 10 (October 1, 2001): 1074–78. http://dx.doi.org/10.1515/znb-2001-1016.

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Enaminones react with a variety of active methyl and methylene reagents in presence of ammonium acetate to yield functionally substituted pyridines in good yields. The reaction proceeded via initial Michael addition across the double bond followed by cyclization. The reaction of enaminone with aromatic aldehyde in acetic acid/ammonium acetate afforded the dihydropyridine that was oxidized to the corresponding pyridine.

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6

Liu, Weibing, Cui Chen, and Qing Zhang. "FeCl3-PTSA Co-Catalysed Highly Regio- and Stereo-Selective Synthesis of β-Functionalised Enamine Derivatives." Journal of Chemical Research 36, no. 3 (March 2012): 175–77. http://dx.doi.org/10.3184/174751912x13306054094882.

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β-Enaminone derivatives are useful synthetic precursors. β- N-Substituted ( E)-enaminones and β-N-substituted ( E)-aminoacrylates were synthesised with high regio- and stereo-selectivity via using the co-catalytic system of FeCl3/PTSA, which also provides a new way to the formation of C–O bond.

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7

Hassan, Mohamed M., and Mona H. Alhalafi. "Synthesis, Structural Determination, and Antioxidant Activities of Acyclic and Substituted Heterocyclic Phosphonates Linearly Linked 4-hydroxy-2(1H)-quinolinone." Molecules 27, no. 18 (September 13, 2022): 5960. http://dx.doi.org/10.3390/molecules27185960.

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The chemical reactivity of 3-[(E)-3-(dimethylamino)-2-propenoyl]-4-hydroxy-1-methy-2(1H)-quinolinone (1) towards some phosphorus reagents was studied. The enaminone 1 was cyclized into pyranoquinolinylphosphonate 2 via treatment with diethyl phosphite in basic medium. However, its reaction with triethoxy phosphonoacetate gave the substituted oxopyranylphosphonate 3. Using the same reaction conditions, both thioxopyridinylphosphonate 4 and oxopyranylphosphonate 5 were produced via a reaction of enaminone 1 with both diethyl 2-amino-2-thioxoethylphosphonate and diethyl vinylphosphonate, respectively, in low yields. In addition, the two novel oxopyridinylphosphonates 6 and 7 were obtained by treatment of enaminone 1 with a diethyl cyanomethylphosphonate reagent. Two oaxathiaphosphininyl derivatives, 8 and 9, were obtained by treatment of the enaminone 1 with O, O-diethyl dithiophosphoric acid under different reaction conditions. Diazaphosphininyl 11 and oxazaphosphininyl 12 derivatives were obtained in excellent yields using a P-phenylphosphonic diamide reagent under different reaction conditions. The treatment of the enaminone 1 with phosphorus pentasulfide produced the non-phosphorylated product thioxothiopyranoquinolinone 13. Finally, the enaminone was turned into oxathiaphosphininyl 14 using Lawesson’s reagent. The possible reaction mechanisms of the formation of these products were discussed. The structures of newly isolated products were established by elemental analysis and spectral tools. The compounds were evaluated for their antioxidant activities.

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8

Szafraniec, Anna, Marcin Grajda, Hanna Jędrzejewska, Agnieszka Szumna, and Waldemar Iwanek. "Enaminone Substituted Resorcin[4]arene—Sealing of an Upper-Rim with a Directional System of Hydrogen-Bonds." International Journal of Molecular Sciences 21, no. 20 (October 11, 2020): 7494. http://dx.doi.org/10.3390/ijms21207494.

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The paper presents the synthesis of an enaminone resorcin[4]arene via a thermally activated o-quinomethide. The crystal structure indicates that in the solid state all enaminone units participate in a unidirectional seam of 12 intramolecular hydrogen bonds that are formed around the cavity. The molecule exhibits C2 symmetry, with two opposite-laying enaminone units directed inside the cavity (“in”), and the other two units outside the cavity (“out”). In the solution the enaminone resorcin[4]arene exists as a mixture of conformers with distribution controlled by temperature and solvent. The experimental data are compared with the results of theoretical calculations using DFT B3LYP/6-31G(d,p) and fast semi-empirical DFTB/GFN2-xTB method in various solvents.

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9

Al-Romaizan, Abeer N., Nesreen S. Ahmed, and Sherin M. Elfeky. "Design, Synthesis, and Biological Evaluation of Triazolyl- and Triazinyl-Quinazolinediones as Potential Antitumor Agents." Journal of Chemistry 2019 (February 3, 2019): 1–12. http://dx.doi.org/10.1155/2019/9104653.

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Novel 6(3-1H-1,2,4-triazol-1-yl)-3-phenylquinazoline-2,4(1H,3H)-diones (7a–e) were synthesized from different enaminones (6a–e) with 6-hydrazinyl-3-phenylquinazoline-2,4(1H,3H)-dione. 2,6(4-2-Substituted-1,3,5-triazin-1(2H)-yl)-3-phenylquinazoline-2,4(1H,3H)-diones (8a–k) were synthesized from the reaction of 1-(2,4-dioxo-3-phenyl-1,2,3,4-tetrahydroquinazolin-6-yl)thiourea, urea, or guanidine (3a–c) with enaminones (6a–e), and a series from 3-substituted-2-imino-1,3,5-triazin-1(2H)-yl-sulfonyl-phenyl-1-methylquinazoline-2,4(1H,3H)-dione (12a–j) were obtained from the reaction of N-(diaminomethylene)-4-(1-methyl-2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl)benzenesulfonamide (11) with the enaminone (6a–j). The antitumor activity of the synthesized compounds was evaluated against two human cell lines: human colon carcinoma HCT116 and human hepatocellular carcinoma HEP-G2. Some of the tested compounds showed significant potency compared to the reference drug staurosporin.

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10

Filkale, Adelew Estifanos, and Chandni Pathak. "Dinuclear cobalt complexes supported by biphenol and binaphthol-derived bis(salicylaldimine) ligands: synthesis, characterization and catalytic application in β-enaminone synthesis from 1,3-dicarbonyl compounds and aliphatic amines." New Journal of Chemistry 44, no. 35 (2020): 15109–21. http://dx.doi.org/10.1039/d0nj00052c.

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11

Li, Yi, Xiaoji Cao, Yunyun Liu, and Jie-Ping Wan. "Regioselective three-component synthesis of 2,3-disubstituted quinolines via the enaminone modified Povarov reaction." Organic & Biomolecular Chemistry 15, no. 45 (2017): 9585–89. http://dx.doi.org/10.1039/c7ob02411h.

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12

Wagger, Jernej, David Bevk, Anton Meden, Jurij Svete, and Branko Stanovnik. "Enaminone-Based Synthesis of Dipodazine Derivatives." Helvetica Chimica Acta 89, no. 2 (February 2006): 240–48. http://dx.doi.org/10.1002/hlca.200690026.

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13

Šenica, Luka, Uroš Grošelj, Marta Kasunič, Drago Kočar, Branko Stanovnik, and Jurij Svete. "Synthesis of Enaminone-Based Vinylogous Peptides." European Journal of Organic Chemistry 2014, no. 15 (March 13, 2014): 3067–71. http://dx.doi.org/10.1002/ejoc.201402033.

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14

Knieß, Astrid, Margit Gruner, and Roland Mayer. "Reaktionsverhalten von β-Oxo-carbonsäurederivaten der Anthracenreihe bei der Synthese von Pyrazolen / On the Reaction Behavior of ß-Oxo Carbonic Acid Derivatives of the Anthracene Series in Pyrazole Synthesis." Zeitschrift für Naturforschung B 54, no. 9 (September 1, 1999): 1133–37. http://dx.doi.org/10.1515/znb-1999-0908.

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ß-Oxo-1 and 9-anthracenepropionate (6 and 7) reacts with DMF-acetale to enaminones 10 and 11. The reaction of 2-(dimethylamino)methylen-substituted ß-oxo-1 -anthracenepropionate (10) with hydrazines yields 5-(l-anthracenyl)-pyrazol-4-carboxylates (13). In contrast, the cyclocondensation of 3-(9-anthracenyl)-2-(dimethylamino)methylen-3-oxo-propionate (11) with hydrazine hydrochlorides gives 4-(9-anthracenoyl)-5-hydroxy-pyrazoles (14). This is caused by the sterical hindrance of the carbonyl group of the anthracene derivatives in position 9; thus, the cyclocondensation proceeds via reaction of the ester group of the enaminone 11.

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15

Ambethkar, Sethurajan, Vediappen Padmini, and Nattamai Bhuvanesh. "A one-pot sequential five-component domino reaction for the expedient synthesis of polysubstituted pyrroles." New Journal of Chemistry 40, no. 5 (2016): 4705–9. http://dx.doi.org/10.1039/c5nj03444b.

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16

Wan, Jie-Ping, Youyi Zhou, Yunyun Liu, and Shouri Sheng. "Metal-free oxidative carbonylation on enaminone CC bond for the cascade synthesis of benzothiazole-containing vicinal diketones." Green Chemistry 18, no. 2 (2016): 402–5. http://dx.doi.org/10.1039/c5gc01821h.

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17

Klintworth, Robin, Garreth L. Morgans, Stefania M. Scalzullo, Charles B. de Koning, Willem A. L. van Otterlo, and Joseph P. Michael. "Silica gel and microwave-promoted synthesis of dihydropyrrolizines and tetrahydroindolizines from enaminones." Beilstein Journal of Organic Chemistry 17 (October 13, 2021): 2543–52. http://dx.doi.org/10.3762/bjoc.17.170.

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A wide range of N-(ethoxycarbonylmethyl)enaminones, prepared by the Eschenmoser sulfide contraction between N-(ethoxycarbonylmethyl)pyrrolidine-2-thione and various bromomethyl aryl and heteroaryl ketones, underwent cyclization in the presence of silica gel to give ethyl 6-(hetero)aryl-2,3-dihydro-1H-pyrrolizine-5-carboxylates within minutes upon microwave heating in xylene at 150 °C. Instead of functioning as a nucleophile, the enaminone acted as an electrophile at its carbonyl group during the cyclization. Yields of the bicyclic products were generally above 75%. The analogous microwave-assisted reaction to produce ethyl 2-aryl-5,6,7,8-tetrahydroindolizine-3-carboxylates from (E)-ethyl 2-[2-(2-oxo-2-arylethylidene)piperidin-1-yl]acetates failed in nonpolar solvents, but occurred in ethanol at lower temperature and microwave power, although requiring much longer time. A possible mechanism for the cyclization is presented, and further functionalization of the newly created pyrrole ring in the dihydropyrrolizine core is described.

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18

Zhong, Shanshan, Yu Lu, Yan Zhang, Yunyun Liu, and Jie-Ping Wan. "Synthesis of β,β-diaryl propiophenones via palladium-catalyzed domino arylboronation, elimination and enone hydroarylation of enaminones." Organic & Biomolecular Chemistry 14, no. 26 (2016): 6270–73. http://dx.doi.org/10.1039/c6ob01038e.

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19

Olyaei, Abolfazl, Amir Mohamadi, and Nilufar Rahmani. "Green synthesis of new lawsone enaminones and their Z/E(CC)-isomerization induced by organic solvent." RSC Advances 11, no. 21 (2021): 12990–94. http://dx.doi.org/10.1039/d1ra01858b.

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The synthesis of a new class of lawsone enaminone derivatives by using lawsone, triethyl orthoformate and aromatic amines in the presence of guanidinium chloride under solvent-free conditions has been developed.

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20

Bhat, Mashooq Ahmad, Mohamed A. Al-Omar, Ahmed M. Naglah, Atef Kalmouch, and Abdullah Al-Dhfyan. "Synthesis and Characterization of Novel Biginelli Dihydropyrimidinone Derivatives Containing Imidazole Moiety." Journal of Chemistry 2019 (May 13, 2019): 1–7. http://dx.doi.org/10.1155/2019/3131879.

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Enaminone, (2E)-1-[4-(1H-imidazol-1-yl) phenyl]-4-methylpent-2-en-1-one (II) was synthesized by refluxing 1-[4-(1H-imidazol-1-yl) phenyl] ethan-1-one (I) with dimethylforamide dimethylacetal (DMF–DMA) under solvent-free condition for 12 hours. Finally, the dihydropyrimidinone derivatives containing imidazole moiety (1–15) were obtained by reacting enaminone, (2E)-1-[4-(1H-imidazol-1-yl) phenyl]-4-methylpent-2-en-1-one (II) with urea and different substituted benzaldehydes in the presence of glacial acetic acid. Dihydropyrimidinone derivatives containing imidazole moiety were synthesized in excellent yield by means of a simple and efficient method. All the compounds were confirmed by elemental analysis. The structures of all the compounds were confirmed by modern spectroscopic methods.

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21

Alshahrani, Saeed, Saied M. Soliman, Abdullah Saleh Alamary, Abdullah Mohammed Al-Majid, Matti Haukka, Sammer Yousuf, and Assem Barakat. "Synthesis of Enaminones-Based Benzo[d]imidazole Scaffold: Characterization and Molecular Insight Structure." Crystals 10, no. 10 (October 21, 2020): 955. http://dx.doi.org/10.3390/cryst10100955.

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(E)-1-(1H-Benzo[d]imidazol-2-yl)-3-(dimethylamino)prop-2-en-1-one 2 was synthesized by one-pot synthesis protocol of 2-acetyl benzo[d]imidazole with dimethylformamide dimethylacetal (DMF-DMA) in xylene at 140 °C for 8 h. Reaction of enaminone derivative 1 with acetylacetone in the presence of AcOH/NH4OAc under reflux afforded the cyclized pyridino-benzo[d]imidazole derivative 3. The latter compound was converted into the corresponding β-enaminone 4 with DMF-DMA. The single crystal X-ray diffraction technique eventually confirmed the assigned chemical structure of the N-alkyl-β-enaminone 2 and pyridino-benzo[d]imidazole derivative 3. N-alkyl-β-enaminone 2 crystallized in the monoclinic space group P21/n with unit cell parameters of a = 9.8953(3) Å, b = 5.7545(2) Å, c = 21.7891(7) Å, and β =100.627(2)°, and with one molecule per asymmetric unit. On the other hand, compound 3 crystallized in the orthorhombic crystal system and space group P212121 with unit cell parameters of a = 6.82950(10) Å, b = 8.00540(10) Å, c = 22.4779(2) Å, and also with one molecule per asymmetric unit. Based on Hirshfeld analysis, the H...H (51.3%), O...H (10.0%), N...H (10.3%), and C...H (27.6%) contacts in 2 and the H...H (46.8%), O...H (9.9%), N...H (13.0%), and C...H (21.6%) in addition to the C…C (6.7%) interactions in 3 are the most important towards crystal stability via molecular packing. The main difference is the presence of π–π interaction among the molecular units of 3 but not in 2. The calculated 1H and 13C NMR chemical shifts showed good agreements with experimental data. Electronic properties and reactivity parameters of both compounds are also calculated and compared.

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22

Wu, Wenfeng, Zhuxian Wang, Qun Shen, Qiang Liu, and Huoji Chen. "Fe-Catalyzed enaminone synthesis from ketones and amines." Organic & Biomolecular Chemistry 17, no. 28 (2019): 6753–56. http://dx.doi.org/10.1039/c9ob01137d.

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23

Bhat, Mashooq A., Mohamed A. Al-Omar, Ahmed M. Naglah, and Abdullah Al-Dhfyan. "Facile synthesis and anticancer activity of novel dihydropyrimidinone derivatives." Polish Journal of Chemical Technology 24, no. 1 (March 1, 2022): 23–28. http://dx.doi.org/10.2478/pjct-2022-0004.

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Abstract The enaminone, (2E)-3-(dimethylamino)-1-(3,4,5-trimethoxyphenyl) prop-2-en-1-one was prepared by refluxing 3,4,5-trimethoxy acetophenone with dimethylformamide dimethylacetal (DMF–DMA) without solvent for 12 h. The dihydropyrimidinone derivatives (1–9) were prepared by reacting enaminone, substituted benzaldehydes and urea in glacial acetic acid. The compounds (1–9) were synthesized in significant yield using one step multicomponent reaction. Structures of all the novel synthesized compounds were characterized and confirmed by various spectroscopic methods. The compounds were evaluated for their anti-cancer activity against HepG2 cancer cell line. Compound 9 displayed significant anti-cancer activity. During the apoptotic assay, it showed a significant increase in necrosis from 1.97% to 12.18% as compared to the control. Mechanism of anti-proliferation was performed by cell cycle distribution assay, which showed a decrease in G2+M from 12.90 to 8.13 as compared to control.

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24

Bhat, Mashooq A., Mohamed A. Al-Omar, Ahmed M. Naglah, and Abdullah Al-Dhfyan. "Biginelli Synthesis of Novel Dihydropyrimidinone Derivatives Containing Phthalimide Moiety." Journal of Chemistry 2020 (March 9, 2020): 1–5. http://dx.doi.org/10.1155/2020/4284628.

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A new series of novel Biginelli compounds, 5-benzoyl-substituted phenyl-3,4-dihydropyrimidin-2(1H)-one-1H-isoindole-1,3(2H)-dione (1−10), were synthesized from enaminone, 2-{4-[(2E)-3-(dimethylamino)prop-2-enoyl]phenyl}-1H-isoindole-1,3(2H)-dione (IV), which was synthesized by refluxing 2-(4-acetylphenyl)-1H-isoindole-1,3(2H)-dione (III), with dimethylformamide-dimethylacetal (DMF-DMA) without solvent for 12 h. The compound 2-(4-acetylphenyl)-1H-isoindole-1,3(2H)-dione (III) was obtained by reacting phthalic anhydride (I) with para-aminoacetophenone (II) in glacial acetic acid for 2 h. The dihydropyrimidinone derivatives containing phthalimide moiety (1–10) were obtained by reacting enaminone, 2-{4-[(2E)-3-(dimethylamino) prop-2-enoyl] phenyl}-1H-isoindole-1,3(2H)-dione (IV), with urea and different substituted benzaldehydes in the presence of glacial acetic acid for 3 h. Simple and efficient method was employed to synthesize the dihydropyrimidinone derivatives containing phthalimide moiety. Structures of all the synthesized compounds were characterized by spectroscopic methods.

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25

Shen, Jinhai, Xifa Yang, Fuyuan Wang, Yue Wang, Guolin Cheng, and Xiuling Cui. "Base-mediated regiospecific cascade synthesis of N-(2-pyridyl)pyrroles from N-propargylic β-enaminones." RSC Advances 6, no. 54 (2016): 48905–9. http://dx.doi.org/10.1039/c6ra08987a.

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26

Edafiogho, Ivan O., Jacqueline A. Moore, Vida A. Farrar, Jesse M. Nicholson, and K. R. Scott. "Synthesis, Reactions, and Preliminary Evaluations of Enaminone Esters." Journal of Pharmaceutical Sciences 83, no. 1 (January 1994): 79–84. http://dx.doi.org/10.1002/jps.2600830119.

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27

Wan, Jie-Ping, Chunping Wang, and Yunyun Liu. "Direct synthesis of enaminone functionalized biaryl ethers by CuI-catalyzed O-arylation of enaminone functionalized phenols." Organic & Biomolecular Chemistry 9, no. 19 (2011): 6481. http://dx.doi.org/10.1039/c1ob05947e.

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28

Yu, Qing, Yating Zhang, and Jie-Ping Wan. "Ambient and aerobic carbon–carbon bond cleavage toward α-ketoester synthesis by transition-metal-free photocatalysis." Green Chemistry 21, no. 12 (2019): 3436–41. http://dx.doi.org/10.1039/c9gc01357a.

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With a low loading of Rose Bengal (1 mol%) and green LED irradiation, α-ketoesters are efficiently synthesized with excellent product diversity and selectivity via the ambient cleavage of the enaminone CC double bond.

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29

Mahmoud, Huda K., Hanadi A. Katouah, Marwa F. Harras, and Thoraya A. Farghaly. "A New Reactive Ketenaminal: Synthesis, Coupling Reaction, Tautomeric Study, Docking and Antimicrobial Evaluation of the Products." Medicinal Chemistry 16, no. 6 (September 7, 2020): 761–73. http://dx.doi.org/10.2174/1573406415666190716153425.

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Background: One of the most successful reagents used in the synthesis of the reactive enaminone is DMF-DMA, but it is very expensive with harmful effects on the human health and reacts with special compounds to generate the enaminone such as active methylene centers. Aim: In this article, we synthesized a new ketenaminal by simple method with inexpensive reagents (through desulfurization in diphenylether). Methods: Thus, a novel reactive ketenaminal (enaminone) was synthesized from the desulfurization of 2-((2-(4-chlorophenyl)-2-oxoethyl)thio)-5,7-bis(4-methoxyphenyl)pyrido[2,3-d]pyrimidin- 4(3H)-one with diphenylether. The starting keteneaminal was coupled with diazotized anilines via the known coupling conditions to give a new series of 2-(4-chlorophenyl)-1-(2-(arylhydrazono)-2- oxoethyl)-5,7-bis(4-methoxy-phenyl)pyrido[2,3-d]pyrimidin-4(1H)-ones. Results: The structures of the new compounds were elucidated based on their IR, 1H-NMR, 13CNMR, and Mass spectra. Moreover, the potency of these compounds as antimicrobial agents has been evaluated. The results showed that some of the products have high activity nearly equal to that of the used standard antibiotic. Additionally, the docking study was done to get the binding mode of the synthesized compounds with the binding site of the DHFR enzyme. The results of molecular docking of the synthesized arylhydrazono compounds are able to fit in DHFR binding site with binding energies ranging from -4.989 to -8.178 Kcal/mol. Conclusion: Our goal was achieved in this context by the synthesis of new ketenaminal from inexpensive reagents, which was utilized in the preparation of bioactive arylhydrazone derivatives.

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30

Škrlep, Luka, Andreja Čerček-Hočevar, Renata Jakše, Branko Stanovnik, and Jurij Svete. "A Simple Synthesis of 1-Substituted Diethyl Pyrrole-3,4-dicarboxylates." Zeitschrift für Naturforschung B 64, no. 6 (June 1, 2009): 683–88. http://dx.doi.org/10.1515/znb-2009-0614.

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A series of 1-substituted diethyl 1H-pyrrole-3,4-dicarboxylates 4a - o were prepared in 14 - 93% yield by acid-catalysed treatment of diethyl 2,3-bis[(E,E)-(dimethylamino)-methylidene]succinate (2) with various aliphatic and (hetero)aromatic primary amines 3a - o. The configuration of the C=C double bonds in the bis-enaminone 2 was determined by 1H NMR and HMBC spectroscopy.

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31

Shah, Nirav, Nimesh Shah, Manish Patel, and Ranjan Patel. "Design, synthesis and antimicrobial activity of new biquinoline derivatives." Journal of the Serbian Chemical Society 77, no. 3 (2012): 279–86. http://dx.doi.org/10.2298/jsc110630197s.

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A simple and efficient method has been developed for the synthesis of some novel biquinoline derivatives bearing a thiazole moiety through a onepot three-component condensation of 2-chlro-3-formylquinolines, ethyl cyanoacetate and ?-enaminone using catalytic amount of piperidine in refluxing ethanol. These molecules were evaluated in vitro for their antibacterial and antifungal activity. Most of the compounds exhibited moderate antibacterial and antifungal activity against all the tested strains.

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32

Al-Saleh, Balkis, Nouria Al-Awadi, Halema Al-kandari, Mervat Mohammed Abdel-Khalik, and Mohamed Hilmy Elnagdi. "Studies with 2H pyranones: Synthesis of new 3-substituted-4-hydroxy-2H-pyran-2-ones." Journal of Chemical Research 2000, no. 1 (January 2000): 16–17. http://dx.doi.org/10.3184/030823400103165725.

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3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 1a condensed with N,N-dimethylformamide dimethyl acetal yielding the enaminone 3a. The latter reacted with a variety of reagents affording pyridine derivatives 11, benzofuranoylpyranes 14 and 17, pyranylpyranes 22, pyranylpyrazole 29a,b and pyranylisoxazole 33.

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33

Wan, Jie-Ping, Chunping Wang, and Yunyun Liu. "ChemInform Abstract: Direct Synthesis of Enaminone Functionalized Biaryl Ethers by CuI-Catalyzed O-Arylation of Enaminone Functionalized Phenols." ChemInform 43, no. 7 (January 23, 2012): no. http://dx.doi.org/10.1002/chin.201207060.

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34

Liang, Xiao, Xin Huang, Mingteng Xiong, Kexin Shen, and Yuanjiang Pan. "Copper(i)-catalyzed N–H olefination of sulfonamides for N-sulfonyl enaminone synthesis." Chemical Communications 54, no. 60 (2018): 8403–6. http://dx.doi.org/10.1039/c8cc04385j.

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35

Scapin, Elisandra, Paulo R. S. Salbego, Caroline R. Bender, Alexandre R. Meyer, Anderson B. Pagliari, Tainára Orlando, Geórgia C. Zimmer, et al. "Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-a]pyrimidine/2-azidopyrimidines." Beilstein Journal of Organic Chemistry 13 (November 10, 2017): 2396–407. http://dx.doi.org/10.3762/bjoc.13.237.

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An efficient synthesis methodology for a series of tetrazolo[1,5-a]pyrimidines substituted at the 5- and 7-positions from the cyclocondensation reaction [CCC + NCN] was developed. The NCN corresponds to 5-aminotetrazole and CCC to β-enaminone. Two distinct products were observed in accordance with the β-enaminone substituent. When observed in solution, the compounds can be divided into two groups: (a) precursor compounds with R = CF3 or CCl3, which leads to tetrazolo[1,5-a]pyrimidines in high regioselectivity with R at the 7-position of the heterocyclic ring; and (b) precursor compounds with R = aryl or methyl, which leads to a mixture of compounds, tetrazolo[1,5-a] pyrimidines (R in the 5-position of the ring) and 2-azidopyrimidines (R in the 4-position of the ring), which was attributed to an equilibrium of azide–tetrazole. In the solid state, all compounds were found as 2-azidopyrimidines. The regiochemistry of the reaction and the stability of the products are discussed on the basis of the data obtained by density functional theory (DFT) for energetic and molecular orbital (MO) calculations.

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36

Ho, Yuh-Wen, and Maw Cherng Suen. "Thioxopyrimidine in Heterocyclic Synthesis I: Synthesis of Some Novel 6-(Heteroatom-substituted)-(thio)pyrimidine Derivatives." Journal of Chemistry 2013 (2013): 1–15. http://dx.doi.org/10.1155/2013/765243.

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A series of novel N-cycloalkanes, morpholine, piperazines, pyrazole, pyrimidine, benzimidazolo[1,2-a]pyrimidine, 1,2,3,4-tetrazolo[1,5-a]pyrimidine, azopyrazolo[1,5- a]pyrimidine, pyrimido[4', 5':3,4]pyrazolo[1,5-a]pyrimidines and pyridine derivatives incorporating a 5-cyano-4-methyl-2-phenyl-(thio)pyrimidine moiety were obtained by the intramolecular cyclization of 6-methylthio-pyrimidine, 6-(benzoylmethyl)thio- pyrimidine and 2-[(5-cyano-4-methyl-2-phenylpyrimidin-6-yl)thio]-3-dimethyl- amino-1-phenyl-prop-2-en-1-one with appropriate amines and enaminone compounds, respectively. The structure of all new synthesized compounds was established from their spectral data, elemental analysis and the X-ray crystal analysis.

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37

Tomažin, Urša, Branko Alič, Anja Kristl, Aleš Ručigaj, Uroš Grošelj, Franc Požgan, Matjaž Krajnc, Bogdan Štefane, Urška Šebenik, and Jurij Svete. "Synthesis of polyenaminones by acid-catalysed amino–enaminone ‘click’ polymerisation." European Polymer Journal 108 (November 2018): 603–16. http://dx.doi.org/10.1016/j.eurpolymj.2018.07.048.

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38

EDAFIOGHO, I. O., J. A. MOORE, V. A. FARRAR, J. M. NICHOLSON, and K. R. SCOTT. "ChemInform Abstract: Synthesis, Reactions, and Preliminary Evaluations of Enaminone Esters." ChemInform 25, no. 19 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199419100.

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39

Mohammadi, Leila, Mohammad Ali Zolfigol, Mahsa Ebrahiminia, Kenneth P. Roberts, Samira Ansari, Tahereh Azadbakht, and Syed R. Hussaini. "A copper(I)-complexed magnetic nanoparticle catalyst for enaminone synthesis." Catalysis Communications 102 (December 2017): 44–47. http://dx.doi.org/10.1016/j.catcom.2017.08.022.

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40

Abdulsalam, Maysam B., and Ahmed T. Numan. "Synthesis, Characterization, and Biological Activity of Mixed ligand Complexes from 8-Hydroxyquinoline and new Ligand for β-Enaminone." Pakistan Journal of Medical and Health Sciences 16, no. 8 (August 31, 2022): 614–21. http://dx.doi.org/10.53350/pjmhs22168614.

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The synthesized ligand [4-chloro-5-(N-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)sulfamoyl)-2-((furan-2-ylmethyl)amino)benzoic acid] (H2L1) was identified utilizing Fourier transform infrared spectroscopy (FT-IR), 1 H, 13 C – NMR, (C.H.N), Mass spectra, UV-Vis methods based on spectroscopy. To detect mixed ligand complexes, analytical and spectroscopic approaches such as micro-analysis, conductance, UV-Visible, magnetic susceptibility, and FT-IR spectra were utilized. Its mixed ligand complexes [M(L1)(Q)Cl2] [ where M= Co(II), Ni(II), and Cd(II)] and complexes [Pd(L1)(Q)] and [Pt(L1)(Q)Cl2]; [H2L1] =β-enaminone ligand =L1 and Q= 8-Hydroxyquinoline = L2]. The results showed that the complexes were synthesised utilizing the molar ratio M: L1:L2 (1 :1 :1). The formation of six-coordinate octahedral geometry was proposed for metal complexes Co (II), Ni (II), Cd (II), and Pt (IIII), while the Pd (II) complex was square planar. By using the agar well diffusion method, the ligands and complexes were evaluated for antibacterial activity against Staphylococcus aureus, Escherichia coli. The studies demonstrate that the ligand and its complexes have variable activity against the bacterial types, Some of the complexes had an effect on bacteria, while others had less inhibitory action than the ligand. Also, the produced ligand and its metal complexes have been tested for fungi (Candida albicans );the complexes exhibited suppressing activity against fungi compared to the ligand prepared from them. Keywords: β-enaminones, 5,5-dimethylcyclohexane-1,3-dione , Furosemide, Mixed-ligand complexes, 8-Hydroxyquinoline.

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41

Liu, Ting, Jie-Ping Wan, and Yunyun Liu. "Metal-free enaminone C–N bond cyanation for the stereoselective synthesis of (E)- and (Z)-β-cyano enones." Chemical Communications 57, no. 72 (2021): 9112–15. http://dx.doi.org/10.1039/d1cc03292e.

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The C–N bond cyanation of tertiary enaminones has been realized for the stereoselective synthesis of both (E)- and (Z)-β-cyano enones under mild metal-free conditions, providing highly practical approaches for the synthesis of β-cyano enones.

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42

Kadhom, Hassan J., Ahmed T. Numan, and Eman M. Atiyah. "Synthesis and Characterization of New Ligand for β-enaminone and its Mixed Ligand Complexes with Some Metal Ions and Evaluation of their Biological Activity." INTERNATIONAL JOURNAL OF DRUG DELIVERY TECHNOLOGY 12, no. 02 (June 25, 2022): 640–47. http://dx.doi.org/10.25258/ijddt.12.2.30.

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The synthesized ligand (3-(2-amino-5-(3,4,5-tri-methoxybenzyl)pyrimidin-4-ylamino)-5,5-dimethylcyclohex-2-enone] [H1L1] was characterized via fourier transform infrared spectroscopy (FTIR), 1H, 13C – NMR, Mass spectra, (CHN analysis), UV-vis spectroscopic approaches. Analytical and spectroscopic techniques like chloride content, micro-analysis, magnetic susceptibility UV-visible, conductance, and FTIR spectra were used to identify mixed ligand complexes. Its (ML13ph) mixed ligand complexes [M= Co (II), Ni (II), Cu (II), Zn (II), and Cd (II); (H1L1) = β-enaminone ligand=L1 and (3ph) =3-aminophenol= L2]. The results demonstrate that the complexes are produced with a molar ratio of M: L1:L2 (1:1:1). To generate the appropriate complex, a tetradentate β-enaminone ligand with N3O donor atoms is coordinated to Co(II), Ni(II), Cu(II), Zn(II), and Cd (II) ions. The synthesized ligand and its mixed ligand complexes have been tested against various pathogenic fungi and bacteria for antifungal and antibacterial activities. In this case, when compared with conventional antibiotic ciprofloxacin, the biological activity regarding such compounds was good.

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43

Cooper, Melanie M., and John W. Huffman. "Reaction of an enaminone with 1-nitrocyclopentene: synthesis of a triquinane." Journal of the Chemical Society, Chemical Communications, no. 5 (1987): 348. http://dx.doi.org/10.1039/c39870000348.

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44

Cimarelli, Cristina, Gianni Palmieri, and Mercedes Camalli. "Stereoselective preparation of enaminone lithium dianions: Synthesis of N,N-dimethylcarbamoylenaminones." Tetrahedron 53, no. 20 (May 1997): 6893–902. http://dx.doi.org/10.1016/s0040-4020(97)00320-7.

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45

Shi, Pengfei, Lili Wang, Kehao Chen, Jie Wang, and Jin Zhu. "Co(III)-Catalyzed Enaminone-Directed C–H Amidation for Quinolone Synthesis." Organic Letters 19, no. 9 (April 20, 2017): 2418–21. http://dx.doi.org/10.1021/acs.orglett.7b00968.

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46

Chang, Lina, Tao Guo, Ziyi Wang, Shaozhong Wang, and Zhu-Jun Yao. "Azepinoindole Synthesis via a N-Bromosuccinimide-Induced Cycloisomerization of Enaminoester/Enaminone." Journal of Organic Chemistry 82, no. 3 (January 23, 2017): 1567–74. http://dx.doi.org/10.1021/acs.joc.6b02760.

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47

Baškovč, Jernej, David Bevk, Branko Stanovnik, and Jurij Svete. "Bis-enaminone Based Parallel Solution-Phase Synthesis of 1,4-Dihydropyridine Derivatives." Journal of Combinatorial Chemistry 11, no. 3 (May 11, 2009): 500–507. http://dx.doi.org/10.1021/cc900032c.

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48

Farghaly, Thoraya A., Magda A. Abdallah, and Mohamed R. Abdel Aziz. "Synthesis of a NovelTri-enaminone as Building Block for Polyaza-heterocycles." Journal of Heterocyclic Chemistry 54, no. 1 (May 3, 2016): 699–705. http://dx.doi.org/10.1002/jhet.2644.

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49

Gajengi, Aravind L., Takehiko Sasaki, and Bhalchandra M. Bhanage. "Effect of solvent ratio and counter ions on the morphology of copper nanoparticles and their catalytic application in β-enaminone synthesis." RSC Advances 6, no. 104 (2016): 101800–101807. http://dx.doi.org/10.1039/c6ra22017g.

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This work reports the synthesis of shape selective copper nanoparticles (NPs) using a microwave irradiation method, using diverse ratios of an ethylene glycol (EG)/water system and their catalytic application in β-enaminones synthesis.

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50

Štanfel, Urša, Tomaž Kotnik, Sebastijan Ričko, Uroš Grošelj, Bogdan Štefane, Klemen Pirnat, Ema Žagar, Boštjan Genorio, and Jurij Svete. "Synthesis of Optically and Redox Active Polyenaminones from Diamines and α,α’-Bis[(dimethylamino)methylidene]cyclohexanediones." Polymers 14, no. 19 (October 1, 2022): 4120. http://dx.doi.org/10.3390/polym14194120.

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New oligo- and polyenaminones with Mw ~ 7–50 KDa were prepared in high yields by transaminative amino-enaminone polymerization of regioisomeric bis[(dimethylamino)methylidene]cyclohexanediones with alkylene and phenylenediamines. The polymers obtained are practically insoluble in aqueous and organic solvents and exhibit film-forming properties, UV light absorption at wavelengths below 500 nm, and redox activity. These properties indicate a promising application potential of these polymers, which could find use in optical and optoelectronic applications and in energy storage devices.

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