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Journal articles on the topic 'Benzylideneaminothiazol- 4(5H)-ones'

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Published: 4 June 2025

Last updated: 1 August 2025

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1

Sharad, K. Awate, V. Patil Suresh, S. Dhivare Ravindra, and G. Khanapure Renukacharya. "Microwave-Assisted Synthesis, Characterization and Antimicrobial Potencies of N-Substituted Iminothiazodin-4-One Derivatives." International Journal of Research in Pharmaceutical Sciences 11, no. 1 (2020): 589–95. https://doi.org/10.26452/ijrps.v11i1.1861.

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<strong>Abstract</strong> The biggest and most multifaceted class of organic compounds includes heterocyclic compounds. Currently, several heterocyclic compounds are identified, and persistently gratefulness to tremendous synthetic work and synthetic usefulness, the number is increasing exponentially. In most fields of science, including medicinal, pharmaceutical, and agro-chemistry, heterocyclic compounds have a function, and biochemistry is also another area. In this research article, the green approach is administered for achieving the nitrogen, oxygen, and sulphur centered five-membered he

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2

Mielgo, Antonia, and Claudio Palomo. "1H-Imidazol-4(5H)-ones and thiazol-4(5H)-ones as emerging pronucleophiles in asymmetric catalysis." Beilstein Journal of Organic Chemistry 12 (May 9, 2016): 918–36. http://dx.doi.org/10.3762/bjoc.12.90.

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Asymmetric catalysis represents a very powerful tool for the synthesis of enantiopure compounds. In this context the main focus has been directed not only to the search for new efficient chiral catalysts, but also to the development of efficient pronucleophiles. This review highlights the utility and first examples of 1H-imidazol-4(5H)-ones and thiazol-4(5H)-ones as pronucleophiles in catalytic asymmetric reactions.

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3

Toplak, Renata, Jurij Svete, Simona Golič Grdadolnik, and Branko Stanovnik. "Methyl (Z)-2-[(Benzyloxycarbonyl)amino]-3-dimethyl- aminopropenoate in the Synthesis of Heterocyclic Systems. Synthesis of (Benzyloxycarbonyl)amino Substituted Fused Pyrimidinones." Collection of Czechoslovak Chemical Communications 64, no. 2 (1999): 177–89. http://dx.doi.org/10.1135/cccc19990177.

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Methyl (Z)-2-[(benzyloxycarbonyl)amino]-3-dimethylaminopropenoate (1) was used as a reagent for preparation of 3-[(benzyloxycarbonyl)amino] substituted 4H-pyrido[1,2-a]pyrimidin-4-ones 17-21, 4H-pyrimido[1,2-b]pyridazin-4-ones 22 and 23, 5H-[1,2,4]triazolo[2,3-a]- pyrimidin-5-one 24, 5H-thiazolo[3,2-a]pyrimidin-5-one 25, and 4H-pyrazino[1,2-a]pyrimidin-4-one 26. Removal of the benzyloxycarbonyl group by catalytical transfer hydrogenation with Pd/C in the presence of cyclohexene is selective to give 3-amino-4H-pyrido[1,2-a]- pyrimidin-4-ones 27-30 in 85-92% yields, or with hydrogen bromide in a

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4

Chiba, Arisa, Ryoko Tanaka, Mayuno Hotta, et al. "Stereochemistry of N-Acyl-5H-dibenzo[b,d]azepin-7(6H)-ones." Molecules 28, no. 12 (2023): 4734. http://dx.doi.org/10.3390/molecules28124734.

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The stereochemical properties of N-acyl-5H-dibenzo[b,d]azepin-7(6H)-ones (2a–c), which inhibit potassium channels in T cells, were examined by freezing their conformational change due to 4-methyl substitution. N-Acyl-5H-dibenzo[b,d]azepin-7(6H)-ones exist as pairs of enantiomers [(a1R, a2R), (a1S, a2S)], and each atropisomer is separable at room temperature. An alternate procedure for preparing 5H-dibenzo[b,d]azepin-7(6H)-ones involves the intramolecular Friedel–Crafts cyclization of N-benzyloxycarbonylated biaryl amino acids. Consequently, the N-benzyloxy group was removed during the cyclizat

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5

Yan, Yan-Mei, Hao-Yang Li, Min Zhang, et al. "One-Pot Synthesis of [1,2,3]Triazolo[1,5-a]quinoxalin-4(5H)-ones by a Metal-Free Sequential Ugi-4CR/Alkyne–Azide Cycloaddition Reaction." Synlett 31, no. 01 (2019): 73–76. http://dx.doi.org/10.1055/s-0037-1610737.

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A convenient and one-pot approach to prepare [1,2,3]triazolo[1,5-a]quinoxalin-4(5H)-ones by a metal-free sequential Ugi-4CR/alkyne–azide cycloaddition reaction has been developed. The reaction of 2-azidobenzenamines, aldehydes, propiolic acids, and isocyanides produced the Ugi adducts, which were transformed to the [1,2,3]triazolo[1,5-a]quinoxalin-4(5H)-ones in moderate to good yields via alkyne–azide cycloaddition reaction.

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6

Wang, Mingan, Zhao Yu, Liu Xinlei, Wang Weiwei, and Geng Rui. "Cs2CO3-Promoted C-3 Alkylation of 4-[(2,2-Difluoroethyl)amino]-5,5-disubstituted Furan-2(5H)-ones with Heteroarylmethyl Chlorides." Synthesis 50, no. 20 (2018): 4055–62. http://dx.doi.org/10.1055/s-0037-1609548.

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4-(2,2-Difluoroethylamino)-3-(heteroarylmethyl)-5,5-disubstituted furan-2(5H)-ones were regioselectively synthesized via C-3 alkylation of 4-(2,2-difluoroethylamino)-5,5-disubstituted furan-2(5H)-ones with heteroarylmethyl chlorides using Cs2CO3 as a base in 62–85% yields. Their structures were characterized by 1H and 13C NMR, HRMS (ESI), and X-ray diffraction. This C-alkylation selectivity was rationalized by bulky hindrance and electron-withdrawing effects.

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7

Hodgetts, Kevin J., and Mark T. Kershaw. "Synthesis of 2-Aryl-oxazolo[4,5-c]quinoline-4(5H)-ones and 2-Aryl-thiazolo[4,5-c]quinoline-4(5H)-ones." Organic Letters 5, no. 16 (2003): 2911–14. http://dx.doi.org/10.1021/ol0350285.

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8

Zhu, Bo, Shuai Qiu, Jiangtao Li, Michelle L. Coote, Richmond Lee, and Zhiyong Jiang. "Asymmetric [4 + 2] annulation of 5H-thiazol-4-ones with a chiral dipeptide-based Brønsted base catalyst." Chemical Science 7, no. 9 (2016): 6060–67. http://dx.doi.org/10.1039/c6sc02039a.

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9

Fang, Y., and G. K. Tranmer. "Expedited access to thieno[3,2-c]quinolin-4(5H)-ones and benzo[h]-1,6-naphthyridin-5(6H)-ones via a continuous flow photocyclization method." Organic & Biomolecular Chemistry 14, no. 46 (2016): 10799–803. http://dx.doi.org/10.1039/c6ob02279k.

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10

Nayak, Swarnagowri, and Santosh L Gaonkar. "A NEW MICROWAVE-ASSISTED METHOD FOR THE SYNTHESIS OF 2-SUBSTITUTED-THIAZOL-4(5H)-ONE VIA HANTZSCH CONDENSATION." Rasayan Journal of Chemistry 15, no. 01 (2022): 310–15. http://dx.doi.org/10.31788/rjc.2022.1516578.

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A new microwave-assisted method is developed for the synthesis of 2-substituted-thiazol-4(5H)-ones via Hantzsch condensation by a simple experimental protocol without using any catalyst. The products were isolated in excellent yield without any purification. Synthesized compounds were characterized by applying FTIR, 1H NMR, 13C NMR, and mass spectral studies and a plausible mechanism is proposed for the formation of the product. The method is versatile for the preparation of a new class of 2-substituted-thiazol-4(5H)-ones.

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11

C. Majumdar, Krishna, Anup K. Kundu, and Paritosh Biswas. "Synthesis of Furo[2,3-c]quinolin-4(5H)-ones." HETEROCYCLES 51, no. 10 (1999): 2399. http://dx.doi.org/10.3987/com-99-8633.

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12

Khan, Muhammad Naeem, Misbahul Ain Khan, Noreen Aslam, Pir Bakhsh Khan, and Ehsan ul Haq. "Tetracyclic Heteroaromatic Systems-Synthesis of Ethoxycarbonylphenylpyrido[3',2':5,6] Thiopyranoquinolines." Pakistan Journal of Scientific & Industrial Research Series A: Physical Sciences 64, no. 3 (2021): 191–94. http://dx.doi.org/10.52763/pjsir.phys.sci.64.3.2021.191.194.

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7-benzylideneamino-5H-thiochromeno[2,3-b]pyridin-5-ones and 9-benzylideneamino-5H-thio- chromeno[2,3-b]pyridin-5-ones, on reaction with ethyl pyruvate to afford 1-ethoxycarbonyl-3-phenyl-12H- pyrido[3',2':5,6]thiopyrano[3,2-f]quinoline-12-ones and 4-ethoxycarbonyl-2-phenyl-7H- pyrido[3',2':5,6]thiopyrano[3,2-h]quinoline-7-ones respectively by the two different methods. These products were precipitated by addition of ethanol, water (1:1), were purified by recrystalizing from appropriate solvents and were characterized from their IR, 1H-NMR, mass spectra and elemental analysis data.

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13

Kunick, C. "Fused Azepinones with Antitumor Activity." Current Pharmaceutical Design 5, no. 3 (1999): 181–94. http://dx.doi.org/10.2174/1381612805666230109214720.

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Based on the observation that some simple [l]benzazepin-2-ones exhibit in vivo antitumor activity, studies directed to several new structure classes with this partial motif have been reported recently, comprising 7,l 2-dihydro-indolo[3,2-d][l ]benzazepin- 6(5H)-ones (paullones), 5H-quinolino[3,2-d][ I ]benzazepin-6(7H)-ones, 2,4-diaryl-5H• pyrido[3,2-d][ I ]benzazepin-6(7H)-ones, spiro[ l-benzazepine-4, l '-cyclohexane] deri va tives, and naphthannelated benzazepinones. For the syntheses of these heterocyclic compounds, IH-[l]benzazepine-2,5(3H,4H)-diones were employed as readily available ;

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14

Girgis, Adel S., and I. S. Ahmed-Farag. "Synthesis of Novel 2-Alkoxy-5H-benzo[6,7]cyclohepta[1,2-b]pyridine-3-carbonitriles." Zeitschrift für Naturforschung B 58, no. 7 (2003): 698–703. http://dx.doi.org/10.1515/znb-2003-0716.

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Reaction of 6-arylmethylene-6,7,8,9-tetrahydro-5H-benzocyclo-hepten-5-ones (1) with malononitrile in the appropriate alcohol in the presence of sodium afforded the corresponding 2-alkoxy-4-aryl- 6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridine-3-carbonitriles (2) and not their isomeric forms 2-alkoxy-4-aryl-6,7-dihydro-5H-benzo[3,4]-cyclohepta[1,2-c]pyridine-1-carbonitriles (3). The proposed structure was confirmed via independent synthesis of (2) through the reaction of 6,7,8,9- tetrahydro-5-benzocycloheptenone (4) with the appropriate ylidenemalononitriles 5 under the same reaction conditi

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15

Gao, Wangxi, Lixin Niu, Tao Wang, Yong Liang, Ding Wang, and Zunting Zhang. "Synthesis of cis/trans-dihydrochromenones via a photoinduced rearrangement of 4-phenyl-3-aryl/cyclohexenylcoumarins." Organic & Biomolecular Chemistry 19, no. 33 (2021): 7176–80. http://dx.doi.org/10.1039/d1ob01058a.

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Irradiation of 4-phenyl-3-arylcoumarins and 4-phenyl-3-alkenylcoumarins in EtOH with 313 nm UV light under an argon atmosphere at room temperature gave cis-dihydrobenzofurochromen-16-ones and trans-1,2,3,4,4a,14b-hexahydro-5H-phenanthro[9,10-c]chromen-5-ones in good yields.

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16

Wang, Zhiyong, Lijun Xue, Yiyi He, Licong Weng, and Ling Fang. "Access to Functionalized 3H-Pyrrolo[2,3-c]quinolin-4(5H)-ones and Thieno[2,3-c]quinolin-4(5H)-ones via Domino Reaction of 4-Alkynyl-3-bromoquinolin-2(1H)-ones." Journal of Organic Chemistry 79, no. 20 (2014): 9628–38. http://dx.doi.org/10.1021/jo501753p.

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17

Gašparová, Renata, Pavol Koiš, Margita Lácová, Silvia Kováčová, and Andrej Boháč. "Synthesis, reactions and antineoplastic activity of 3-(2-oxo-2H-chromen-3-yl)-2-oxo-2H,5H-pyrano[3,2-c]chromene derivatives." Open Chemistry 11, no. 4 (2013): 502–13. http://dx.doi.org/10.2478/s11532-012-0184-1.

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AbstractThe key 3-(2-oxo-2H-chromen-3-yl)-2-oxo-2H,5H-pyrano[3,2-c]chromen-5-yl acetates 3 were synthesized in high yields by cyclocondensation of 4-oxo-4H-chromen-3-carbaldehydes 1 with coumarin-3-acetic acids 2 under mild conditions. The reaction pathway involves aldol condensation and subsequent intramolecular lactonization to afford 2-oxo-2H,5H-pyrano[3,2-c]chromene skeleton 3. Further treatment of acetates 3 with alcohols, water or nitrogen containing compounds led to 5-alkoxy-, 5-hydroxy- or 5-acylamino-2H,5H-pyrano[3,2-c]chromen-2-ones 4-6 via nucleophilic substitution of acetyloxy grou

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18

Prim, Damien, Delphine Joseph, and Gilbert Kirsch. "New Compounds from 6,7-Dihydrobenzo[c]thiophen-4(5H)-ones." Liebigs Annalen 1996, no. 2 (2006): 239–45. http://dx.doi.org/10.1002/jlac.199619960214.

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19

Zhang, Shaowei, Demin Ren, Xiaolian Hu, Xingliang Fu, and Xiaofang Li. "Synthesis of Spiro Indazole-Tetrahydrothiophenes via Sulfa-Michael/Aldol Cascade Reactions." Journal of Chemical Research 41, no. 11 (2017): 641–44. http://dx.doi.org/10.3184/174751917x15094552081170.

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The sulfa-Michael/aldol cascade reaction of 5-arylmethylidene-1-phenyl-6,7-dihydro-1H-indazol-4(5H)-ones and 1,4-dithiane-2,5-diol yielded novel 2′-(4-aryl)-4′-hydroxy-1-phenyl-4′,5′,6,7-tetrahydro-2′H-spiro[indazole-5,3′-thiophen]-4(1H)-ones in moderate yields. The structures of all the products were characterised thoroughly by NMR, IR and HRMS, together with X-ray crystallographic analysis.

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20

Qiu, Shuai, Choon-Hong Tan, and Zhiyong Jiang. "Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones with N-itaconimides." Beilstein Journal of Organic Chemistry 12 (November 1, 2016): 2293–97. http://dx.doi.org/10.3762/bjoc.12.222.

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A dipeptide-based urea-amide tertiary amine (DP-UAA) was shown to be an effective Brønsted base catalyst for the first asymmetric annulation reaction between 5H-thiazol-4-ones and N-itaconimides. High levels of enantioselectivity (up to 99% ee) and diastereoselectivity (>19:1 dr) were obtained for a series of spirocyclic 1,4-sulfur-bridged piperidinone-based succinimides.

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21

Tasker, Nikhil R., Ettore J. Rastelli, Isabella K. Blanco, et al. "In-flow photooxygenation of aminothienopyridinones generates iminopyridinedione PTP4A3 phosphatase inhibitors." Organic & Biomolecular Chemistry 17, no. 9 (2019): 2448–66. http://dx.doi.org/10.1039/c9ob00025a.

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22

Sadek, Kamal Usef, Ramadan Ahmed Mekheimer, Tahany Mahmoud Mohamed, Moustafa Sherief Moustafa, and Mohamed Hilmy Elnagdi. "Regioselectivity in the multicomponent reaction of 5-aminopyrazoles, cyclic 1,3-diketones and dimethylformamide dimethylacetal under controlled microwave heating." Beilstein Journal of Organic Chemistry 8 (January 4, 2012): 18–24. http://dx.doi.org/10.3762/bjoc.8.3.

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The multicomponent reaction of 5-aminopyrazole derivatives with cyclic 1,3-dicarbonyl compounds and dimethylformamide dimethylacetal (DMFDMA) in DMF at 150 °C under controlled microwave heating afforded regioselectively 8,9-dihydropyrazolo[1,5-a]quinazolin-6(7H)-ones 6 rather than the corresponding dihydropyrazolo[5,1-b]quinazolin-8(5H)-ones 4.

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23

Khlebniсova, T. S., V. G. Zinovich, Yu A. Piven, et al. "1,2,3-Triazole-Containing 1,5,6,7-Tetrahydro-4H-indazol-4-ones and 6,7-Dihydrobenzo[d]isoxazol-4(5H)-ones: Synthesis and Biological Activity." Russian Journal of General Chemistry 93, no. 2 (2023): 268–77. http://dx.doi.org/10.1134/s1070363223020068.

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Abstract Triazole-containing 1,5,6,7-tetrahydro-4H-indazol-4-ones and 6,7-dihydrobenzo[d]isoxazol-4(5H)-ones were synthesized by cyclocondensation of 2-[(1H-1,2,3-triazol-1-yl)acetyl]cyclohexane-1,3-diones with phenylhydrazine (4-fluorophenylhydrazine) or hydroxylamine, respectively. Structure and composition of the obtained compounds were confirmed by 1H, 13C, 19F NMR spectroscopy methods and by data of elemental analysis. Cytotoxic and cytostatic activities of the series of obtained compounds were investigated in vitro against human hepatocellular carcinoma cells HepG2, mammary adenocarcinom

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24

Bourahla, Khadidja, Solène Guihéneuf, Emmanuelle Limanton, et al. "Design and Microwave Synthesis of New (5Z) 5-Arylidene-2-thioxo-1,3-thiazolinidin-4-one and (5Z) 2-Amino-5-arylidene-1,3-thiazol-4(5H)-one as New Inhibitors of Protein Kinase DYRK1A." Pharmaceuticals 14, no. 11 (2021): 1086. http://dx.doi.org/10.3390/ph14111086.

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Here, we report on the synthesis of libraries of new 5-arylidene-2-thioxo-1,3-thiazolidin-4-ones 3 (twenty-two compounds) and new 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones 5 (twenty-four compounds) with stereo controlled Z-geometry under microwave irradiation. The 46 designed final compounds were tested in order to determine their activity against four representative protein kinases (DYR1A, CK1, CDK5/p25, and GSK3α/β). Among these 1,3-thiazolidin-4-ones, the molecules (5Z) 5-(4-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one 3e (IC50 0.028 μM) and (5Z)-5-benzo[1,3]dioxol-5-ylmethylene-2-(p

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25

Lisovenko, Natalya Yu, Ekaterina R. Nasibullina, Svetlana S. Kharitonova, and Olga A. Myshkina. "Simple Synthesis of Substituted 3-Hydroxyfuran-2(5H)-ones." Synthesis 53, no. 11 (2021): 1955–61. http://dx.doi.org/10.1055/s-0040-1705998.

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AbstractA convenient and facile approach to functionalized 4-substituted 3,5-dihydroxy-5-(trichloromethyl)furan-2(5H)-ones was developed. This method is based on regioselective synthesis of novel furan-2,3-diones containing the trichloromethyl group and subsequent hydrolysis. The structures of compounds were unambiguously confirmed by single-crystal X-ray diffraction.

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26

Girgis, Adel S., Hanaa M. Hosni, and Atef Kalmouch. "Synthetic approaches towards 5H-[1]benzopyrano[3,4-c]pyridin-5-ones." Journal of Chemical Research 2005, no. 1 (2005): 38–40. http://dx.doi.org/10.3184/0308234053431004.

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The construction of 5H-[1]benzopyrano[3,4-c]pyridin-5-ones 2 was achieved through the reaction of 1-aryl-3-(2-hydroxyphenyl)-2-propen-1-ones 1 with malononitrile in alcoholic KOH solution affording the compound 2 along with 2-alkoxy-4-amino-6-aryl-3,5-pyridinedicarbonitriles 3. Single crystal X-ray diffraction of 3e confirmed the established structure and excluded the formation of the isomeric product 4.

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27

Wang, Ziyang, Anqi Huang, Fang Fang, Pengfei Li, Guokai Liu, and Wenjun Li. "Non-hydrogen bond catalyst-mediated diastereoselective conjugate additions of 5H-oxazol-4-ones to o-hydroxyphenyl-substituted p-quinone methides." Organic & Biomolecular Chemistry 18, no. 35 (2020): 6807–11. http://dx.doi.org/10.1039/d0ob01558j.

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An efficient DBU-catalyzed conjugate addition of 5H-oxazol-4-ones to o-hydroxyphenyl-substituted p-quinone methides has been developed, affording the valuable diarylmethanes in high yields with excellent diastereoselectivity.

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28

Wiethan, Carson, Steffany Z. Franceschini, Helio G. Bonacorso, and Mark Stradiotto. "Synthesis of pyrazolo[1,5-a]quinoxalin-4(5H)-ones via one-pot amidation/N-arylation reactions under transition metal-free conditions." Organic & Biomolecular Chemistry 14, no. 37 (2016): 8721–27. http://dx.doi.org/10.1039/c6ob01407k.

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An efficient one-pot procedure for the synthesis of new pyrazolo[1,5-a]quinoxalin-4(5H)-ones from easily prepared 1-(2-chlorophenyl-5-ethylcarboxylate)pyrazoles and various primary alkylamines is described.

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29

Bourke, Sharon, and Frances Heaney. "The synthesis of 1,2,7,11b-Tetrahydroisoxazolo[2,3-d][1,4]benzodiazepin-6(5H)-ones and 1,3,3a,9b-tetrahydroisoxazolo[4,3-c]quinolin-4(5H)-ones." Tetrahedron Letters 36, no. 41 (1995): 7527–30. http://dx.doi.org/10.1016/0040-4039(95)01523-x.

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30

Lancelot, Jean-Charles, Bertrand Letois, Carmela Saturnono, Paolo De Caprariis, and Max Robba. "A NOVEL SYNTHESIS OF 2,3-DIHYDRO[1,5]BENZOTHIAZEPIN-4(5H)-ONES." Organic Preparations and Procedures International 24, no. 2 (1992): 204–8. http://dx.doi.org/10.1080/00304949209355701.

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31

Kochikyan, T. V., M. A. Samvelyan, and V. S. Arutyunyan. "Synthesis of 2-substituted aminothiazol-4(5H)-ones proceeding from carboxylactones." Russian Journal of Organic Chemistry 47, no. 8 (2011): 1204–8. http://dx.doi.org/10.1134/s1070428011080148.

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32

Suzuki, Fumio, Takeshi Kuroda, Takashi Kawakita, et al. "New bronchodilators. 3. Imidazo[4,5-c][1,8]naphthyridin-4(5H)-ones." Journal of Medicinal Chemistry 35, no. 26 (1992): 4866–74. http://dx.doi.org/10.1021/jm00104a013.

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33

SUZUKI, Fumio, Takeshi KURODA, Hiroaki HAYASHI, et al. "New Bronchodilators. II. 3H-Imidazo(4,5-c)quinolin-4(5H)-ones." CHEMICAL & PHARMACEUTICAL BULLETIN 40, no. 12 (1992): 3245–52. http://dx.doi.org/10.1248/cpb.40.3245.

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34

Qiao, Baokun, Yongqiang An, Qian Liu, et al. "Organocatalytic Asymmetric Michael Addition of 5H-Oxazol-4-ones to Nitroolefins." Organic Letters 15, no. 10 (2013): 2358–61. http://dx.doi.org/10.1021/ol401062z.

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35

Majumdar, Krishna C., Anup K. Kundu, and Paritosh Biswas. "ChemInform Abstract: Synthesis of Furo[2,3-c]quinolin-4(5H)-ones." ChemInform 31, no. 5 (2010): no. http://dx.doi.org/10.1002/chin.200005160.

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36

Gautam, Poonam, and Ram P. Chaudhary. "Carbodiimide Mediated Synthesis of new Thiazolidin-4-Ones and Thiazinan-4-Ones from Thiosemicarbazone Derivatives of 6,7-Dihydro-1H-Indazole-4(5H)-Ones." Journal of Chemical Research 38, no. 4 (2014): 226–30. http://dx.doi.org/10.3184/174751914x13940194215183.

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37

Beattie, Nicola J., Craig L. Francis, Andris J. Liepa, and G. Paul Savage. "Spiroheterocycles via Regioselective Cycloaddition Reactions of Nitrile Oxides with 5-Methylene-1H-pyrrol-2(5H)-ones." Australian Journal of Chemistry 63, no. 3 (2010): 445. http://dx.doi.org/10.1071/ch09479.

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Substituted 5-methylene-1H-pyrrol-2(5H)-ones underwent a 1,3-dipolar cycloaddition reaction with nitrile oxides to give the corresponding spiro heterocycles. Critical to this reaction was the development of a biphasic system for base-induced dehydrohalogenation of hydroximoyl chlorides, to give nitrile oxides, in the presence of a base-sensitive dipolarophile. A substituted N-tolyl 5-methylene-1H-pyrrol-2(5H)-one exhibited atropisomerism, which in turn led to a 4:1 facial selectivity during cycloaddition.

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38

Amalʼchieva, Olga A., Vyacheslav S. Grinev, Ilya A. Demeshko, and Alevtina Yu Yegorova. "Interaction of 3H-furan-2-ones and 4-oxobutanoic acids with 2-(aminophenyl)methanol." Izvestiya of Saratov University. Chemistry. Biology. Ecology 22, no. 3 (2022): 244–50. http://dx.doi.org/10.18500/1816-9775-2022-22-3-244-250.

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Reactions of 4-oxobutanoic acids as well as their cyclic analogues 3H-furan-2-ones with 1,3-binucleophilic reagent (2-aminophenyl) methanol lead to the formation of 1-R-5H-benzo[d]pyrrolo[2,1-b][1,3]oxazines and 3a-R-2,3,3a-trihydro-5H-benzo[d]pyrrolo[2,1-b][1,3]oxazin- 1-ones, respectively. Quantum-chemical calculations of the Fukui reactivity indices and local hardness have substantiated the mechanisms of the reactions carried out. According to the calculated values of the Fukui indices, in the (2-aminophenyl)methanol molecule, compared to the hydroxyl, the amino group has a higher nucleophi

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39

Surya Prakash Rao, H., and Ashiq Hussain Padder. "Blaise reaction: synthesis, skeletal diversification of C(4) substituted 5-ylidenepyrrol-(5H)-ones and the role of the strategically located ester on the reactivity of the nitriles." New Journal of Chemistry 44, no. 21 (2020): 9010–17. http://dx.doi.org/10.1039/d0nj00231c.

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We have achieved a simple and convenient synthesis of several C(4) substituted 5-ylidenepyrrol-(5H)-ones from 3-aryl/heteroaryl/alkyl 3-cyanopropionates and ethyl/methyl bromoacetates via a useful variation of the classical Blaise reaction.

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40

Bernhardt, Paul V., and Curt Wentrup. "Structures of 4-Iminopyrido[1,2-a]pyrimidines, Pyrido[1,2-a]pyrimidin-4-ones, Pyridopyrimidinium Olates, and Thiazolo[3,2-a]pyrimidine Analogues." Australian Journal of Chemistry 65, no. 4 (2012): 371. http://dx.doi.org/10.1071/ch12040.

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The Structure-Correlation Principle of Bürgi and Dunitz is invoked in an analysis of the structures of 2-chloro-8-methyl-4-(2-(4-picolinyl)imino-4H-pyrido[1,2-a]pyrimidine 8, 7-chloro-5-(2-thiazolyl)imino-5H-thiazolo[3,2-a]pyrimidine 9, 2-methylamino-4H-pyrido[1,2-a]pyrimidin-4-one 10, 7-methylthio-5H-thiazolo[3,2-a]pyrimidin-5-one 11, 2,3-dihydro-7-methylthio-5H-thiazolo[3,2-a]pyrimidin-5-one 12, and 1-methyl-2-[(o-tert-butylphenyl)imino]-1,2-dihydropyrido[1,2-a]pyrimidin-1-ium-4-olate 13, which have been determined by X-ray crystallography. The most notable structural peculiarities are the l

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41

Bozhkov, Anatoly, Rustam Akzhyhitov, Nataliia Dobrianska, and Аndrii Bozhkov. "Old rats are not inferior to young ones in their ability to adapt to repeated sequential exposure to copper sulfate pentahydrate." Ageing & Longevity, no. 4 2024 (December 24, 2024): 198–219. https://doi.org/10.47855/jal9020-2024-4-6.

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Abstract. The quality and longevity of life depend on the ability of a biological system to adapt to the continuously changing environmental factors. However, why the success of adaptation varies among individuals and whether there are differences in adaptive reserves between young (3 months old) and aged (20 months old) animals remains unclear. To address these questions, we investigated the relationship between the temporal characteristics of exposure (sequential injection of different doses of copper sulfate pentahydrate, CuSO₄*5H₂O) and adaptive success in young and aged Wistar rats. In ad

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42

Prager, RH, and C. Tsopelas. "Approaches to the Synthesis of 5-Benzylidene-2-imidazolin-4-ones." Australian Journal of Chemistry 43, no. 2 (1990): 367. http://dx.doi.org/10.1071/ch9900367.

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Aromatic aldehydes , but not ketones, can be condensed with glycocyamidine . The corresponding alkylbenzylideneglycocyamidines may be made from glycidic esters by reaction with guanidine, followed by cyclization with acetic anhydride. A number of mono- and di -acetylated derivatives of 6,7-dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)- dione have been prepared, but failed to undergo the Darzens reaction. Bromo- and iodo-2-arylazoimidazoles, protected on nitrogen by the methoxyethoxymethyl group, failed to undergo clean lithiation.

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43

Lu, Xin-Mou, Zhong-Jian Cai, Jian Li, Shun-Yi Wang, and Shun-Jun Ji. "Synthesis of 7-hydroxy-6,7-dihydro-indole and 6′,7′-dihydro-3,7′-biindole derivatives from domino reactions of arylglyoxals or methyl ketones with enamines." RSC Advances 5, no. 64 (2015): 51501–7. http://dx.doi.org/10.1039/c5ra09478j.

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A series of interesting 7-hydroxy-2-aryl-6,7-dihydro-indol-4(5H)-ones 3 was successfully synthesized in moderate to good yields by the domino reactions of different arylglyoxals 1 with enamines 2 under catalyst-free conditions.

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44

Pankova, Alena S., Pavel R. Golubev, Alexander F. Khlebnikov, Alexander Yu Ivanov, and Mikhail A. Kuznetsov. "Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution." Beilstein Journal of Organic Chemistry 12 (November 29, 2016): 2563–69. http://dx.doi.org/10.3762/bjoc.12.251.

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2-(Alkyl(aryl)amino)thiazol-4(5H)-ones can regioselectively be prepared from monoalkyl(aryl)thioureas and maleimides. In solution, the former heterocycles exist in a tautomeric equilibrium with 2-(alkyl(aryl)imino)thiazolidin-4-ones and the substituent on the exocyclic nitrogen atom governs the ratio of these tautomers. Isomers with the alkyl group in the endocyclic position can be obtained from N-methyl(ethyl)thioureas. 2D NMR spectroscopy and DFT calculations rationalize experimental results.

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45

C. Majumdar, Krishna, and Prabir K. Choudhury. "A Regioselective Synthesis of 2-Alkylfuro[3,2-c]quinolin-4(5H)-ones." HETEROCYCLES 32, no. 1 (1991): 73. http://dx.doi.org/10.3987/com-90-5599.

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46

Chimirri, Alba, Silvana Grasso, Anna-Maria Monforte, Giovanni Romeo, and Maria Zappala. "3H-Azirino[1,2-d][1,4]benzodiazepin-4(5H)-ones: Synthesis and Stereochemistry." HETEROCYCLES 36, no. 4 (1993): 691. http://dx.doi.org/10.3987/com-92-6143.

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Aleksanyan, M. V., G. K. Harutyunyan, and S. P. Gasparyan. "Synthesis of Substituted 4-Amino-1,3,5-triaryl-1H-pyrrol-2(5H)-ones." Russian Journal of General Chemistry 94, no. 5 (2024): 1031–39. http://dx.doi.org/10.1134/s1070363224050037.

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48

Zhao, Hai-Yan, and Gang Liu. "Solution-Phase Parallel Synthesis of 2,3-Dihydro-1,5-benzothiazepin-4(5H)-ones." Journal of Combinatorial Chemistry 9, no. 5 (2007): 756–72. http://dx.doi.org/10.1021/cc070036o.

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PRIM, D., D. JOSEPH, and G. KIRSCH. "ChemInform Abstract: New Compounds frrom 6,7-Dihydrobenzo(c)thiophen-4(5H)-ones." ChemInform 27, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199637161.

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50

Letois, Bertrand, Jean Charles Lancelot, Carmela Saturnino, Max Robba, and Paolo De Caprariis. "Synthesis oftrans-thienyl-3-ethoxycarbonyl-2,3-dihydro[1,5]benzothiazepin-4(5H)-ones." Journal of Heterocyclic Chemistry 29, no. 7 (1992): 1769–72. http://dx.doi.org/10.1002/jhet.5570290716.

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