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Journal articles on the topic 'Imidazolidines'

Author: Grafiati

Published: 4 June 2021

Last updated: 26 July 2025

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1

Olyaei, Abolfazl, and Mahdieh Sadeghpour. "Recent advances in the synthesis of highly substituted imidazolidines." RSC Advances 14, no. 42 (2024): 30758–806. http://dx.doi.org/10.1039/d4ra06010e.

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In this highlight, recent advances in the synthesis of highly substituted imidazolidines, chiral imidazolidines with high diastereoselectivities and enantioselectivities, bis-imidazolidines, and spiro-imidazolidines are presented.

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2

Saloutina, L. V., M. I. Kodess, I. N. Ganebnykh, P. A. Slepukhin, V. I. Saloutin, and O. N. Chupakhin. "Heterocycles on the base of bis(trifluoromethyl)imidazolidin-2-ones, 2-aminoethanol and 2-aminophenol." Журнал органической химии 59, no. 4 (2023): 507–15. http://dx.doi.org/10.31857/s0514749223040092.

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Novel trifluoromethyl-containing imidazo-1,4-oxazines have been synthesized through the condensation reaction of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one with 2-aminoethanol (2-AE) and 2-aminophenol (2-APh). Unusual route of the reaction of 1-methyl(phenyl)- 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones with 2-AE has been found, leading to hydroxyethylamino-substituted hydantoins. The interaction of the N-substituted imidazolidines with 2-APh under similar conditions led to formation of rearrangement products, 5,5-bis(trifluoromethyl)hydantoins. The molecular struct

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3

Vaughan, Keith, Shasta Lee Moser, Reid Tingley, M. Brad Peori, and Valerio Bertolasi. "Triazene derivatives of (1,x-)diazacycloalkanes. Part VI. 3-({5,5-Dimethyl-3-[2-aryl-1-diazenyl]-1-imidazolidinyl}methyl)-4,4-dimethyl-1-[2-aryl-1-diazenyl]imidazolidines — Synthesis, characterization, and X-ray crystal structure." Canadian Journal of Chemistry 84, no. 10 (2006): 1294–300. http://dx.doi.org/10.1139/v06-091.

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Reaction of a series of diazonium salts with a mixture of formaldehyde and 1,2-diamino-2-methylpropane affords the 3-({5,5-dimethyl-3-[2-aryl-1-diazenyl]-1-imidazolidinyl}methyl)-4,4-dimethyl-1-[2-aryl-1-diazenyl]imidazolidines (1a–1f) in excellent yield. The products have been characterized by IR and NMR spectroscopic analysis, elemental analysis, and X-ray crystallography. The X-ray crystal structure of the p-methoxycarbonyl derivative (1c) establishes without question the connectivity of these novel molecules, which can be described as linear bicyclic oligomers with two imidazolidinyl group

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4

de Carvalho, Gustavo S. G., Patrícia A. Machado, Daniela T. S. de Paula, Elaine S. Coimbra, and Adilson D. da Silva. "Synthesis, Cytotoxicity, and Antileishmanial Activity of N,N'-Disubstituted Ethylenediamine and Imidazolidine Derivatives." Scientific World JOURNAL 10 (2010): 1723–30. http://dx.doi.org/10.1100/tsw.2010.176.

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This paper describes the preparation of N,N'-disubstituted ethylenediamine and imidazolidine derivatives and their in vitro biological activities againstLeishmaniaspecies. Of the nine synthesized compounds, five displayed a good activity in bothL. amazonensisandL. majorpromastigotes. The compounds 1,2-Bis(p-methoxybenzyl)ethylenediamine (4) and 1,3-Bis(p-methoxybenzyl)imidazolidines (5) showed the best activity on intracellular amastigotes, with IC50values of 2.0 and 9.4 μ/mL, respectively. In addition, none of compounds were cytotoxic against mammalian cells. The leishmanicidal activity can b

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5

Savka, Roman. "2-(Pentafluorophenyl)imidazolidines." Synlett 24, no. 13 (2013): 1735–36. http://dx.doi.org/10.1055/s-0033-1339476.

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6

Arduengo, Anthony J., Roland Krafczyk, Reinhard Schmutzler, et al. "Imidazolylidenes, imidazolinylidenes and imidazolidines." Tetrahedron 55, no. 51 (1999): 14523–34. http://dx.doi.org/10.1016/s0040-4020(99)00927-8.

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7

Katritzky, Alan R., Kazuyuki Suzuki, and Hai-Ying He. "Convenient Syntheses of Unsymmetrical Imidazolidines." Journal of Organic Chemistry 67, no. 9 (2002): 3109–14. http://dx.doi.org/10.1021/jo010868n.

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8

Katritzky, Alan R., Kazuyuki Suzuki, and Hai-Ying He. "Convenient Syntheses of Unsymmetrical Imidazolidines." ChemInform 34, no. 1 (2003): no. http://dx.doi.org/10.1002/chin.200301118.

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9

Liu, Anan, Dongge Ma, Yuhang Qian, et al. "A powerful azomethine ylide route mediated by TiO2 photocatalysis for the preparation of polysubstituted imidazolidines." Organic & Biomolecular Chemistry 19, no. 10 (2021): 2192–97. http://dx.doi.org/10.1039/d0ob02277b.

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10

Sun, Yan-Hua, Yu Xiong, Chu-Qin Peng, Wu Li, Jun-An Xiao, and Hua Yang. "Highly stereoselective construction of novel dispirooxindole–imidazolidines via self-1,3-dipolar cyclization of ketimines." Organic & Biomolecular Chemistry 13, no. 29 (2015): 7907–10. http://dx.doi.org/10.1039/c5ob00954e.

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11

Dardonville, Christophe, Beth A. Caine, Marta Navarro de la Fuente, Guillermo Martín Herranz, Beatriz Corrales Mariblanca, and Paul L. A. Popelier. "Substituent effects on the basicity (pKa) of aryl guanidines and 2-(arylimino)imidazolidines: correlations of pH-metric and UV-metric values with predictions from gas-phase ab initio bond lengths." New Journal of Chemistry 41, no. 19 (2017): 11016–28. http://dx.doi.org/10.1039/c7nj02497e.

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12

Han, Ruiping, Yue Ding, Xueke Jin, and Er-Qing Li. "Silver/palladium relay catalyzed 1,3-dipole annulation/allylation reactions to access fully substituted allyl imidazolidines." Organic & Biomolecular Chemistry 18, no. 4 (2020): 646–49. http://dx.doi.org/10.1039/c9ob02633a.

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13

Mukhopadhyay, Soumendranath, and Subhas Chandra Pan. "Organocatalytic asymmetric synthesis of 2,4-disubstituted imidazolidines via domino addition-aza-Michael reaction." Chemical Communications 54, no. 8 (2018): 964–67. http://dx.doi.org/10.1039/c7cc08338f.

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14

Liu, Yajun, Xiaoxia Liu, Lihong Li, et al. "Identification and Structure-Activity Studies of 1,3-Dibenzyl-2-aryl imidazolidines as Novel Hsp90 Inhibitors." Molecules 24, no. 11 (2019): 2105. http://dx.doi.org/10.3390/molecules24112105.

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Hsp90 (Heat shock protein 90) is involved in various processes in cancer occurrence and development, and therefore represents a promising drug target for cancer therapy. In this work, a virtual screening strategy was employed, leading to the identification of a series of compounds bearing a scaffold of 1,3-dibenzyl-2-aryl imidazolidine as novel Hsp90 inhibitors. Compound 4a showed the highest binding affinity to Hsp90α (IC50 = 12 nM) in fluorescence polarization (FP) competition assay and the strongest anti-proliferative activity against human breast adenocarcinoma cell line (MCF-7) and human

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15

Liu, Anan, Dongge Ma, Yuhang Qian, et al. "Correction: A powerful azomethine ylide route mediated by TiO2 photocatalysis for the preparation of polysubstituted imidazolidines." Organic & Biomolecular Chemistry 19, no. 32 (2021): 7085. http://dx.doi.org/10.1039/d1ob90104d.

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Correction for ‘A powerful azomethine ylide route mediated by TiO2 photocatalysis for the preparation of polysubstituted imidazolidines’ by Anan Liu et al., Org. Biomol. Chem., 2021, 19, 2192–2197, DOI: 10.1039/D0OB02277B.

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16

Zhang, Jing, Yi-Fei Li, Feng-Cheng Jia, Yang Gao, and Xiao-Qiang Hu. "Strain-release enabled [3 + 2] annulation of 3-aminooxetanes with simple CN bonds: facile synthesis of imidazolidines." Organic Chemistry Frontiers 8, no. 23 (2021): 6616–21. http://dx.doi.org/10.1039/d1qo01164b.

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An unprecedented [3+2] annulation of readily available 1,3,5-triazinanes and 3-aminooxetanes is accomplished for the first time, enabling the convenient synthesis of a range of structurally diverse 4-hydroxymethyl imidazolidines.

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17

Muthusamy, Sengodagounder, and Singaravelan Ganesh Kumar. "Copper(i) catalyzed diastereoselective multicomponent synthesis of spiroindolo-pyrrolidines/-imidazolidines/-triazolidines from diazoamides via azomethine ylides." Organic & Biomolecular Chemistry 14, no. 7 (2016): 2228–40. http://dx.doi.org/10.1039/c5ob02322j.

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Investigations of stereoselective studies on three-/four-component reactions in the presence of copper(i) thiophene-2-carboxylate as a catalyst are performed to afford spiroindolo-pyrrolidines/-imidazolidines/-triazolidines in good yields.

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18

Fedoseeva, V. G., E. A. Verochkina, L. I. Larina, and N. V. Vchislo. "Reaction of 2-alkylthio-substituted 2-penten-4-ynals with <i>N</i>,<i>N</i>- and <i>N</i>,<i>O</i>-binucleophiles." Журнал органической химии 59, no. 2 (2023): 271–76. http://dx.doi.org/10.31857/s0514749223020155.

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The condensation of 2-alkylthiosubstituted 2-en-4-ynals with N , N - and N , O -binucleophiles gives the corresponding 1,3-perhydrodiazines, 1,3-imidazolidines, and 1,3-oxazolidines with an original combination of substituents.

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19

Luk'yanov, O. A., G. V. Pokhvisneva, and T. V. Ternikova. "N,N?-Diacylated imidazolidines and hexahydropyrimidines." Russian Chemical Bulletin 43, no. 8 (1994): 1376–80. http://dx.doi.org/10.1007/bf00703698.

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20

Arduengo III, Anthony J., Roland Krafczyk, Reinhard Schmutzler, et al. "ChemInform Abstract: Imidazolylidenes, Imidazolinylidenes and Imidazolidines." ChemInform 31, no. 9 (2010): no. http://dx.doi.org/10.1002/chin.200009132.

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21

ASHOK, K. SHAKYA, K. AGRAWAL R., and MISHRA PRADEEP. "Synthesis and Antibacterial Activity of 2-[5'-Alkyl-1',3',4'-thiadiazol-2'-yl]amino-benzothiazole, -benzoxazole,-benzimidazole and -imidazolidines." Journal of Indian Chemical Society Vol. 68, Mar 1991 (1991): 147–48. https://doi.org/10.5281/zenodo.5955601.

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Department of Pharmaceutical Sciences, Dr. H. S. Gour Vishwavidyalaya, Sagar-470 003 <em>Manuscript received 1 August 1990, revised 7 December 1990, accepted 7 March 1991</em> Some new 1 3,4-thiadiazolyiamino-benzothiazole, -benzoxazole, -benzimidazole and -imidazolidines have been synthesised and screened for their antibacterial activity.

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22

Dardonville, Christophe, Beth A. Caine, Marta Navarro de la Fuente, Guillermo Martín Herranz, Beatriz Corrales Mariblanca, and Paul L. A. Popelier. "Correction: Substituent effects on the basicity (pKa) of aryl guanidines and 2-(arylimino)imidazolidines: correlations of pH-metric and UV-metric values with predictions from gas-phase ab initio bond lengths." New Journal of Chemistry 41, no. 19 (2017): 11423. http://dx.doi.org/10.1039/c7nj90071f.

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Correction for ‘Substituent effects on the basicity (pK<sub>a</sub>) of aryl guanidines and 2-(arylimino)imidazolidines: correlations of pH-metric and UV-metric values with predictions from gas-phase ab initio bond lengths’ by Christophe Dardonville et al., New J. Chem., 2017, DOI: 10.1039/c7nj02497e.

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23

Tolpygin, I. E., E. N. Shepelenko, Yu V. Revinskii, et al. "Fluorescent sensors based on 2-substituted imidazolidines." Russian Journal of Organic Chemistry 46, no. 8 (2010): 1181–84. http://dx.doi.org/10.1134/s1070428010080129.

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24

Timmermans, P. B. M. W. M., P. A. van Zwieten, and W. N. Speckamp. "2-(Arylimino)imidazolidines; synthesis and hypotensive activity." Recueil des Travaux Chimiques des Pays-Bas 97, no. 2 (2010): 51–56. http://dx.doi.org/10.1002/recl.19780970208.

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25

Ruan, Min-De, Wei-Qiang Fan, Yun-Zhu Gu, Hua-Jiang Jiang, and Yi-Fei Bu. "Synthesis of 2-(1-Arylcarbonyl-1-arylazomethylidene)-imidazolidines by the Reaction of 2-(Arylcarbonyl-methylidene)imidazolidines with Diazobenzenes." Synthetic Communications 21, no. 12-13 (1991): 1307–13. http://dx.doi.org/10.1080/00397919108021277.

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26

Sultana, Razia, Tarlok S. Lobana, and Alfonso Castineiras. "Chemistry of heterocyclic-2-thiones: in situ generated 1-(4,5-dihydro-3-alkyl-imidazolidin-2-yl)-3-alkyl-imidazolidine-2-thione and triiodide form novel mixed valent CuI–II/CuII complexes." RSC Advances 5, no. 122 (2015): 100579–88. http://dx.doi.org/10.1039/c5ra20449f.

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Copper(i) iodide transforms N-n-butyl-imidazolidine-2-thione in air into 1-(4,5-dihydro-3-butyl-imidazolidin-2-yl)-3-butyl-imidazolidine-2-thione (L-NBu<sup>n</sup>) which formed novel complex, [Cu(κ<sup>2</sup>-N,S-L-NBu<sup>n</sup>)<sub>2</sub>](I<sub>3</sub>)<sub>2</sub>.

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27

Lázár, László, Anikó Göblyös, Ferenc Evanics, Gábor Bernáth, and Ferenc Fülöp. "Ring-Chain tautomerism of 2-aryl-substituted imidazolidines." Tetrahedron 54, no. 44 (1998): 13639–44. http://dx.doi.org/10.1016/s0040-4020(98)00840-0.

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28

LUK'YANOV, O. A., G. V. POKHVISNEVA, and T. V. TERNIKOVA. "ChemInform Abstract: N,N′-Diacylated Imidazolidines and Hexahydropyrimidines." ChemInform 26, no. 12 (2010): no. http://dx.doi.org/10.1002/chin.199512067.

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29

Kavrakova, Ivanka K., and Maria J. Lyapova. "Convenient and Stereospecific Synthesis of trans-1,3-Disubstituted Imidazolidines and Their Transformation to 2,3-Diamino-3-phenylpropanoic Acids." Collection of Czechoslovak Chemical Communications 65, no. 10 (2000): 1580–86. http://dx.doi.org/10.1135/cccc20001580.

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Conversion of the easily available trans-2-oxoimidazolidine-4-carboxylic acid 1 to the corresponding imidazolidines 8 gives after one-step oxidation and ring cleavage the diamino acid 2 in high yield. The difference in the trans-vicinal couplings for the hydrogen-bonded and nonbonded compounds suggests different ring geometry as a result of the balancing effect of the N1 substituent on the "allylic strain".

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30

RUAN, M. D., W. Q. FAN, Y. Z. GU, H. J. JIANG, and Y. F. BU. "ChemInform Abstract: Synthesis of 2-(1-Arylcarbonyl-1-arylazomethylidene)imidazolidines (IV) by the Reaction of 2-(Arylcarbonylmethylidene)imidazolidines (I) with Diazobenzenes." ChemInform 23, no. 8 (2010): no. http://dx.doi.org/10.1002/chin.199208202.

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31

Kibardina, L. K., A. V. Trifonov, A. B. Dobrynin, M. A. Pudovik, and A. R. Burilov. "Some Features of Phosphorylation and Benzoylation of Pyridoxal Imidazolidines." Russian Journal of General Chemistry 91, no. 9 (2021): 1667–73. http://dx.doi.org/10.1134/s1070363221090097.

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32

A. Perillo, Isabel, Graciela Buldain, and Alejandra Salerno. "Spectroscopic Analysis of Imidazolidines. Part IV: 13C-NMR Spectroscopy." HETEROCYCLES 60, no. 9 (2003): 2103. http://dx.doi.org/10.3987/com-03-9811.

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33

Li, Zhifang, and Yongmin Zhang. "LOW VALENT TITANIUM INDUCED ONE-POT SYNTHESIS OF IMIDAZOLIDINES." Organic Preparations and Procedures International 33, no. 2 (2001): 185–87. http://dx.doi.org/10.1080/00304940109356586.

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34

Sheradsky, Tuvia, and Norbert Itzhak. "Desulphuration of sulphur bridged hexahydrotriazines: ring contraction to imidazolidines." Journal of the Chemical Society, Perkin Transactions 1, no. 1 (1989): 33. http://dx.doi.org/10.1039/p19890000033.

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35

Li, Jing, Shaozhong Wang, Jun Hu, and Weixing Chen. "Low-valent titanium induced one pot syntheses of imidazolidines." Tetrahedron Letters 40, no. 10 (1999): 1961–62. http://dx.doi.org/10.1016/s0040-4039(99)00123-9.

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36

Naito, Hiroyuki, Takeshi Hata, and Hirokazu Urabe. "Facile preparation of N-protected 2-alkylidene-1,3-imidazolidines." Tetrahedron Letters 49, no. 14 (2008): 2298–301. http://dx.doi.org/10.1016/j.tetlet.2008.02.006.

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37

Pudovik, M. A., S. A. Terent’eva, A. B. Dobrynin, et al. "2-(2-Hydroxyphenyl)imidazolidines and their O-phosphorylated derivatives." Russian Journal of General Chemistry 87, no. 1 (2017): 60–65. http://dx.doi.org/10.1134/s107036321701011x.

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38

Olyaei, Abolfazl, Mohsen Karbalaei Karimi, and Reza Razeghi. "A one-pot stereoselective synthesis of novel polyfunctionalized imidazolidines." Tetrahedron Letters 54, no. 42 (2013): 5730–33. http://dx.doi.org/10.1016/j.tetlet.2013.08.029.

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39

Avalos, Martı́n, Reyes Babiano, Pedro Cintas, et al. "Atropisomeric carbohydrate imidazolidines: a novel class of nonbiaryl atropisomers." Tetrahedron: Asymmetry 10, no. 21 (1999): 4071–74. http://dx.doi.org/10.1016/s0957-4166(99)00428-0.

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40

Alexakis, Alexandre, Isabelle Aujard, Julien Pytkowicz, Sylvain Roland, and Pierre Mangeney. "Unusually facile palladium catalysed oxidation of imidazolidines and oxazolidines." Journal of the Chemical Society, Perkin Transactions 1, no. 9 (2001): 949–51. http://dx.doi.org/10.1039/b010089g.

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41

Seebach, Dieter, Elmar Pfammatter, Volker Gramlich, et al. "Diastereoselective Michael Additions of Chiral Imidazolidines to Trityl Enones." Liebigs Annalen der Chemie 1992, no. 11 (1992): 1145–51. http://dx.doi.org/10.1002/jlac.1992199201188.

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42

Tolpygin, I. E., E. N. Shepelenko, Yu V. Revinskii, et al. "ChemInform Abstract: Fluorescent Sensors Based on 2-Substituted Imidazolidines." ChemInform 42, no. 8 (2011): no. http://dx.doi.org/10.1002/chin.201108125.

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43

Mehra, Vishu, Pardeep Singh та Vipan Kumar. "β-Lactam-synthon-interceded diastereoselective synthesis of functionally enriched thioxo-imidazolidines, imidazolidin-2-ones, piperazine-5,6-diones and 4,5-dihydroimidazoles". Tetrahedron 68, № 40 (2012): 8395–402. http://dx.doi.org/10.1016/j.tet.2012.08.005.

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44

Jia, Hao, Zhenyan Guo, Honglei Liu, Biming Mao, Xueyan Shi та Hongchao Guo. "Tandem nucleophilic addition–cycloaddition of arynes with α-iminoesters: two concurrent pathways to imidazolidines". Chemical Communications 54, № 51 (2018): 7050–53. http://dx.doi.org/10.1039/c8cc03806f.

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The tandem nucleophilic addition-cycloaddition reaction of arynes with α-iminoesters gave functionalized imidazolidine derivatives with high yields, complete regioselectivities, and excellent diastereo- and enantioselectivities.

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45

Smolobochkin, A. V., E. A. Kuznetsova, A. S. Gazizov, A. R. Burilov, and M. A. Pudovik. "Synthesis of new imidazolidin-2-ones based on the reaction of 1-(2,2-dimethoxyethyl)urea with <i>C</i>-nucleophiles." Журнал общей химии 93, no. 6 (2023): 835–39. http://dx.doi.org/10.31857/s0044460x23060021.

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The acid-catalyzed reaction of 1-(2,2-dimethoxyethyl)ureas with aromatic and heterocyclic nucleophiles leads to the formation of new imidazolidin-2-ones. The proposed method makes it quite easy to introduce the required pharmacophore group into position 4 of the imidazolidine cycle.

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46

Ashweek, Neil J., Iain Coldham, Thomas F. N. Haxell, and Steven Howard. "Preparation of diamines by lithiation–substitution of imidazolidines and pyrimidines." Organic & Biomolecular Chemistry 1, no. 9 (2003): 1532–44. http://dx.doi.org/10.1039/b301502e.

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47

Dousse, G., H. Lavayssière, and J. Satgé. "Reactions D'Echange a Partir de Dioxolannes, Oxazolidines et Imidazolidines Germanies." Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry 19, no. 1 (1989): 49–74. http://dx.doi.org/10.1080/00945718908048051.

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48

Kagabu, Shinzo, Koichi Moriya, Katsuhiko Shibuya, Yumi Hattori, Shin-ichi Tsuboi, and Shiokawa Kozo. "1-(6-Halonicotinyl)-2-nitromethylene-imidazolidines as Potential New Insecticides." Bioscience, Biotechnology, and Biochemistry 56, no. 2 (1992): 362–63. http://dx.doi.org/10.1271/bbb.56.362.

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49

Yavari, Issa, Nooshin Zahedi, and Mohammad Reza Halvagar. "A tandem synthesis of 4,5-bis(arylimino)-2-(alkylimino)imidazolidines." Monatshefte für Chemie - Chemical Monthly 148, no. 8 (2017): 1439–44. http://dx.doi.org/10.1007/s00706-016-1909-1.

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50

Coldham, Iain, Robert A. Judkins, and David R. Witty. "Proton abstraction and electrophilic quench at C-2 of imidazolidines." Tetrahedron 54, no. 47 (1998): 14255–64. http://dx.doi.org/10.1016/s0040-4020(98)00877-1.

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