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Journal articles on the topic '2-pyrrolidinones'

Author: Grafiati

Published: 3 June 2025

Last updated: 31 July 2025

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1

Wei, Wen-Ting, Wei-Wei Ying, Wei-Ting Chen, et al. "Room Temperature, Metal-Free, Radical Chloroazidation of 1,6-Enynes." Synlett 29, no. 12 (2018): 1664–68. http://dx.doi.org/10.1055/s-0037-1609752.

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Without employing any transition metal, a mild, practical, and environmentally attractive methodology has been developed for the chloroazidation of 1,6-enynes at room temperature. In this radical cascade process, three new chemical bonds, including C–Cl (Br, I), C–N, and C–C bonds, are formed in one step for the construction of 2-pyrrolidinones. The method is valuable because of its mild reaction conditions, operational simplicity, and the rich biological activity of the corresponding 2-pyrrolidinone products.

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2

Rigo, Benoǐt, Charles Lespagnol, and Marc Pauly. "Studies on pyrrolidinones. A convenient synthesis of 5-cyano-2-pyrrolidinone derivatives." Journal of Heterocyclic Chemistry 23, no. 1 (1986): 183–84. http://dx.doi.org/10.1002/jhet.5570230137.

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3

Ruostesuo, P., and P. Piril�-Honkanen. "Thermodynamic and spectroscopic properties of 2-pyrrolidinones. 2. Dielectric properties of 2-pyrrolidinone in binary mixtures." Journal of Solution Chemistry 19, no. 5 (1990): 473–82. http://dx.doi.org/10.1007/bf00650380.

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4

Ghelfi, Franco, Gianluca Ghirardini, Emanuela Libertini, Luca Forti, and Ugo M. Pagnoni. "Easy approach to 3-benzylimino-2-pyrrolidinones from 3-chloro-4-chloromethyl-2-pyrrolidinones." Tetrahedron Letters 40, no. 49 (1999): 8595–97. http://dx.doi.org/10.1016/s0040-4039(99)01798-0.

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5

Breinbauer, Rolf, Marko Kljajic, and Thomas Schlatzer. "Synthesis of 2-Pyrrolidinones by Palladium-Catalyzed [3+2] Cycloaddition of Isocyanates." Synlett 30, no. 05 (2019): 581–85. http://dx.doi.org/10.1055/s-0037-1610692.

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Pd/DPEphos catalyzes the [3+2] cycloaddition of various alkyl isocyanates with 2-acetoxymethyl-3-allyltrimethylsilane as a synthetic equivalent of trimethylenemethane (TMM). Taking advantage of 2-acetoxymethyl-3-allyltrimethylsilane acting both as nucleophile as well as electrophile this reaction gives a convenient access to 5-ring lactams with an exocyclic alkene moiety. The formation of the β,γ-unsaturated 2-pyrrolidinones occurs without olefin isomerization and without epimerization of the stereogenic centers. Mechanistic investigations suggest an initial N-allylation of the isocyanate foll

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6

Zav'yalov, S. I., and N. E. Kravchenko. "Synthesis of 5-alkylidene-2-pyrrolidinones." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 38, no. 5 (1989): 1087–90. http://dx.doi.org/10.1007/bf00955460.

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7

Ghelfi, Franco, Gianluca Ghirardini, Emanuela Libertini, Luca Forti, and Ugo M. Pagnoni. "ChemInform Abstract: Easy Approach to 3-Benzylimino-2-pyrrolidinones from 3-Chloro-4-chloromethyl-2-pyrrolidinones." ChemInform 31, no. 9 (2010): no. http://dx.doi.org/10.1002/chin.200009117.

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8

Ruostesuo, P., P. Pirilä-Honkanen, and L. Heikkinen. "Thermodynamic and spectroscopic properties of 2-pyrrolidinones. 3. NMR spectroscopic studies on 2-pyrrolidinone in different solvents." Journal of Physical Organic Chemistry 2, no. 7 (1989): 565–72. http://dx.doi.org/10.1002/poc.610020709.

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9

Moutevelis-Minakakis, Panagiota, Eleni Papavassilopoulou, and Thomas Mavromoustakos. "Synthesis of New Optically Active 2-Pyrrolidinones." Molecules 18, no. 1 (2012): 50–73. http://dx.doi.org/10.3390/molecules18010050.

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10

Zaragoza-Galicia, Ivann, Zaira A. Santos-Sánchez, Yazmín I. Hidalgo-Mercado, Horacio F. Olivo, and Moisés Romero-Ortega. "Synthesis of 5-Substituted 2-Pyrrolidinones by Coupling of Organozinc Reagents with Cyclic N-Acyliminium Ions." Synthesis 51, no. 24 (2019): 4650–56. http://dx.doi.org/10.1055/s-0037-1610733.

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A coupling reaction between cyclic N-acyliminium ions with organozinc reagents is described. The cyclic N-acyliminium ions, generated in situ from N-substituted-5-hydroxy-2-pyrrolidinones by treatment with boron trifluoride–diethyl ether complex or titanium tetrachloride, are trapped by the organozinc reagent, which is formed from an alkyl bromide in the presence of zinc in the same reaction medium. The N-substituted-5-allyl-2-pyrrolidinones generated using this method serve as versatile intermediates for the synthesis of azabicyclic systems with indolizidine and pyrroloazepinolizidine cores.

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11

Alves, José C. F. "2-Pyrrolidinones and 3-Pyrrolin-2-ones: A Study on the Chemical Reactivity of These Structural Moieties." Organic Chemistry International 2011 (September 4, 2011): 1–10. http://dx.doi.org/10.1155/2011/803120.

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The chemical reactivity of 2-pyrrolidinones and 3-pyrrolin-2-ones was evaluated in reactions of addition, nucleophilic substitution, elimination, and reduction as well as the protection of the lactamic nitrogen.

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12

Koseki, Yuji, Shuichi Kusano, Daisuke Ichi, Keiji Yoshida, and Tatsuo Nagasaka. "Stereoselective Synthesis of 5-(1-Hydroxyalkyl)-2-pyrrolidinones Utilizing Oxidation of 5-Alkylidene-2-pyrrolidinones to Acyliminium Ion Precursors." Tetrahedron 56, no. 45 (2000): 8855–65. http://dx.doi.org/10.1016/s0040-4020(00)00841-3.

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13

Stachel, Hans-Dietrich, Hermann Poschenrieder, and Hans Burghard. "Synthese von 5-Alkyliden-3-pyrrolin-2-onen / Synthesis of 5-Alkylidene-3-pyrrolin-2-ones." Zeitschrift für Naturforschung B 41, no. 5 (1986): 640–44. http://dx.doi.org/10.1515/znb-1986-0516.

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By reduction of the tetramic acids 1 or their derivatives 5 and 6 with complex borohydrides the pyrrolidinones 2 and 7 are obtained. Dehydration of 2 and 7 leads to the title compounds 3 and 8, respectively.

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14

Beng, Timothy K., Jasleen Kaur, Ifeyinwa S. Anosike, Benjamin Rentfro, and Shae Newgard. "Revisiting the 1,3-azadiene-succinic anhydride annulation reaction for the stereocontrolled synthesis of allylic 2-oxopyrrolidines bearing up to four contiguous stereocenters." RSC Advances 14, no. 24 (2024): 16678–84. http://dx.doi.org/10.1039/d4ra03156c.

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15

Ruostesuo, P., K. Peltola, U. Salminen, and A. M. Häkkinen. "Charge transfer complexes of N-substituted 2-pyrrolidinones." Spectrochimica Acta Part A: Molecular Spectroscopy 44, no. 1 (1988): 63–67. http://dx.doi.org/10.1016/0584-8539(88)80262-9.

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16

Slough, Greg A. "(Ph3P)3RuCl2 catalyzed equilibration and elimination of α-chloro-N-tosyl-2-pyrrolidinones: A unique route to unsaturated 2-pyrrolidinones." Tetrahedron Letters 34, № 43 (1993): 6825–28. http://dx.doi.org/10.1016/s0040-4039(00)91805-7.

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17

Toja, E., C. Gorini, C. Zirotti, F. Barzaghi, and G. Galliani. "Amnesia-reversal activity of a series of 5-alkoxy-1-arylcarbonyl-2-pyrrolidinones and 5-alkoxy-1-arylmethyl-2-pyrrolidinones." European Journal of Medicinal Chemistry 26, no. 4 (1991): 415–22. http://dx.doi.org/10.1016/0223-5234(91)90102-s.

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18

McAlonan, Helena, James P. Murphy, Paul J. Stevenson, and Alan B. Treacy. "Oxidation of N-(4-methoxybenzyl)-2-pyrrolidinones to N-(4-methoxybenzoyl)-2-pyrrolidinones. Rapid entry to optically active Aniracetam analogues." Tetrahedron 52, no. 38 (1996): 12521–28. http://dx.doi.org/10.1016/0040-4020(96)00732-6.

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19

Png, Zhuang Mao, Jaime R. Cabrera-Pardo, Jorge Peiró Cadahía та Matthew J. Gaunt. "Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams". Chemical Science 9, № 39 (2018): 7628–33. http://dx.doi.org/10.1039/c8sc02855a.

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20

Zhang, Yixin, Haojie Ma, Xingxing Liu, et al. "The synthesis of multi-substituted pyrrolidinones via a direct [3 + 2] cycloaddition of azaoxyallyl cations with aromatic ethylenes." Organic & Biomolecular Chemistry 16, no. 24 (2018): 4439–42. http://dx.doi.org/10.1039/c8ob00899j.

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21

Pirila-Honkanen, Paivi L., and Pirkko A. Ruostesuo. "Thermodynamic and spectroscopic properties of 2-pyrrolidinones. 1. Excess molar volumes of 2-pyrrolidinone + dichloromethane, + dimethyl sulfoxide, + acetone, + 2-propanol, and + water." Journal of Chemical & Engineering Data 32, no. 3 (1987): 303–6. http://dx.doi.org/10.1021/je00049a006.

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22

Qian, Hui, Song Sun, Wanxiang Zhao та Jianwei Sun. "An efficient [3+2] annulation for the asymmetric synthesis of densely-functionalized pyrrolidinones and γ-butenolides". Chemical Communications 56, № 76 (2020): 11295–98. http://dx.doi.org/10.1039/d0cc05188h.

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Disclosed here is a new [3+2] annulation of siloxy alkynes that provides robust access to highly enantioenriched, densely-substituted pyrrolidinones and γ-butenolides, whose direct synthesis remains challenging.

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23

Koseki, Yuji, Shuichi Kusano, Daisuke Ichi, Keiji Yoshida, and Tatsuo Nagasaka. "ChemInform Abstract: Stereoselective Synthesis of 5-(1-Hydroxyalkyl)-2-pyrrolidinones Utilizing Oxidation of 5-Alkylidene-2-pyrrolidinones to Acyliminium Ion Precursors." ChemInform 32, no. 10 (2001): no. http://dx.doi.org/10.1002/chin.200110039.

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24

Morizur, Jean-François, and Lon J. Mathias. "Synthesis of new polyfunctional 2-pyrrolidinones from methyl 2-(carboethoxyhydroxymethyl)acrylate." Tetrahedron Letters 48, no. 31 (2007): 5555–59. http://dx.doi.org/10.1016/j.tetlet.2007.05.122.

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25

Si, Chang-Mei, Zhuo-Ya Mao, Yi-Wen Liu, Zhen-Ting Du, Bang-Guo Wei, and Guo-Qiang Lin. "Stereoselective formation of chiral trans-4-hydroxy-5-substituted 2-pyrrolidinones: syntheses of streptopyrrolidine and 3-epi-epohelmin A." Organic Chemistry Frontiers 2, no. 11 (2015): 1485–99. http://dx.doi.org/10.1039/c5qo00250h.

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A highly diastereoselective approach for synthesis of trans-4-hydroxy-5-substituted 2-pyrrolidinones has been developed. The streptopyrrolidine and 3-epi-epohelmin A were synthesized by this one-pot cascade protocol.

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26

Giese, Bernd, Markus Obkircher, and Wolfgang Seufert. "Photochemical Synthesis of N-Substituted 3-Hydroxy-2-pyrrolidinones." Synlett, no. 7 (2005): 1182–84. http://dx.doi.org/10.1055/s-2005-865229.

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27

Brokaite, K., V. Mickevicius, and G. Mikulskiene. "Synthesis and investigation of some 1,4-disubstituted 2-pyrrolidinones." Chemistry of Heterocyclic Compounds 42, no. 9 (2006): 1158–67. http://dx.doi.org/10.1007/s10593-006-0220-1.

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28

Breña-Valle, Leonardo J., Rodolfo Carreón Sánchez, and Raymundo Cruz-Almanza. "Diastereoselective Alkylation of 1-Benzyl-(5S)-Substituted 2-Pyrrolidinones." Tetrahedron: Asymmetry 7, no. 4 (1996): 1019–26. http://dx.doi.org/10.1016/0957-4166(96)00106-1.

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29

Rigo, BenoǏT, RÉGis Dolaine, Samira El Ghammarti, and Daniel Couturier. "Studies on pyrrolidinones. synthesis ofN-(2-nitrobenzyl)pyroglutamic acid." Journal of Heterocyclic Chemistry 33, no. 4 (1996): 1063–66. http://dx.doi.org/10.1002/jhet.5570330411.

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30

TOJA, E., C. GORINI, C. ZIROTTI, F. BARZAGHI, and G. GALLIANI. "ChemInform Abstract: Amnesia-Reversal Activity of a Series of 5-Alkoxy-1-arylcarbonyl-2- pyrrolidinones and 5-Alkoxy-1-arylmethyl-2-pyrrolidinones." ChemInform 22, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.199141141.

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31

SLOUGH, G. A. "ChemInform Abstract: (Ph3P)3RuCl2-Catalyzed Equilibration and Elimination of α-Chloro- N-tosyl-2-pyrrolidinones: A Unique Route to Unsaturated 2- Pyrrolidinones." ChemInform 25, № 18 (2010): no. http://dx.doi.org/10.1002/chin.199418035.

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32

MCALONAN, H., J. P. MURPHY, P. J. STEVENSON, and A. B. TREACY. "ChemInform Abstract: Oxidation of N-(4-Methoxybenzyl)-2-pyrrolidinones to N-(4- Methoxybenzoyl)-2-pyrrolidinones. Rapid Entry to Optically Active Aniracetam Analogues." ChemInform 28, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199703162.

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33

Gao, Hong, Jing Sun, and Chao-Guo Yan. "Four-component reaction of cyclic amines, 2-aminobenzothiazole, aromatic aldehydes and acetylenedicarboxylate." Beilstein Journal of Organic Chemistry 9 (December 27, 2013): 2934–39. http://dx.doi.org/10.3762/bjoc.9.330.

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The four-component reaction of 2-aminobenzothiazole, aromatic aldehydes, acetylenedicarboxylate and piperidine or pyrrolidine in ethanol afforded the functionalized 2-pyrrolidinones containing both benzothiazolyl and piperidinyl (or pyrrolidinyl) units in good yields. On the other hand, the similar four-component reactions resulted in the functionalized morpholinium or piperidinium 2-pyrrolidinon-3-olates in the presence of p-toluenesulfonic acid.

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34

Brokaite, Kristina, Vytautas Mickevicius, and Gema Mikulskiene. "Synthesis and structural investigation of some 1,4-disubstituted-2-pyrrolidinones." Arkivoc 2006, no. 2 (2005): 61–67. http://dx.doi.org/10.3998/ark.5550190.0007.206.

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35

Tanaka, Kazuhiko, Hidemi Yoda, and Aritsune Kaji. "A Mild and Convenient Synthesis of 3-Methylene-2-pyrrolidinones." Synthesis 1985, no. 01 (1985): 84–86. http://dx.doi.org/10.1055/s-1985-31119.

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36

García-Abuín, Alicia, Diego Gómez-Díaz, José M. Navaza, and Isabel Vidal-Tato. "Surface Tension of Aqueous Solutions of ShortN-Alkyl-2-pyrrolidinones." Journal of Chemical & Engineering Data 53, no. 11 (2008): 2671–74. http://dx.doi.org/10.1021/je800589e.

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37

Victoria Rodriguez-Tzompantzi, Antonio Rosales-López, David M. Aparicio-Solano, Joel L. Terán, and Alan Carrasco-Carballo. "In silico cancer potential of 2-pyrrolidinones from marine origin." GSC Biological and Pharmaceutical Sciences 30, no. 3 (2025): 099–111. https://doi.org/10.30574/gscbps.2025.30.3.0093.

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2-pyrrolidinones present a great variability of biological activities, particularly those of marine origin have given rise to a great diversity of these, so from them, through studies of structural similarity, molecular docking and ADMETx analysis, the potential carcinogenic activity of a library of 33 2-pyrrolidines from various marine organisms was found. Derived from this study, several compounds, such as Cephalimysins M, Cephalimysins N, Amycolactam and Spongialactam A, were shown to be excellent candidates against cancer, via JAK2, JAK3, PDE10A, MAPK14, PDE4A, PDE4B and EGFR, functioning

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38

Afzal, Obaid, Abdulmalik Saleh Alfawaz Altamimi, Mir Mohammad Shahroz, Hemant Kumar Sharma, Yassine Riadi, and Md Quamrul Hassan. "Analgesic and Anticancer Activity of Benzoxazole Clubbed 2-Pyrrolidinones as Novel Inhibitors of Monoacylglycerol Lipase." Molecules 26, no. 8 (2021): 2389. http://dx.doi.org/10.3390/molecules26082389.

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Ten benzoxazole clubbed 2-pyrrolidinones (11–20) as human monoacylglycerol lipase inhibitors were designed on the criteria fulfilling the structural requirements and on the basis of previously reported inhibitors. The designed, synthesized, and characterized compounds (11–20) were screened against monoacylglycerol lipase (MAGL) in order to find potential inhibitors. Compounds 19 (4-NO2 derivative) and 20 (4-SO2NH2 derivative), with an IC50 value of 8.4 and 7.6 nM, were found most active, respectively. Both of them showed micromolar potency (IC50 value above 50 µM) against a close analogue, fat

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39

Kamal, Ahmed, K. Venkata Ramana, A. Venkata Ramana, and A. Hari Babu. "Chemoenzymatic enantioselective synthesis of 3-hydroxy-2-pyrrolidinones and 3-hydroxy-2-piperidinones." Tetrahedron: Asymmetry 14, no. 17 (2003): 2587–94. http://dx.doi.org/10.1016/s0957-4166(03)00548-2.

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40

Piril�-Honkanen, P�ivi. "Thermodynamic and spectroscopic properties of 2-pyrrolidinones. 6. Normalized ET(30) parameters for binary solvent mixtures of 2-pyrrolidinone at 30 and 50�C." Journal of Solution Chemistry 24, no. 7 (1995): 641–49. http://dx.doi.org/10.1007/bf00973232.

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41

Quertenmont, Mathilde, Frédéric C. Toussaint, Thierry Defrance, Kevin Lam, István E. Markó, and Olivier Riant. "Continuous Flow Electrochemical Oxidative Cyclization and Successive Functionalization of 2-Pyrrolidinones." Organic Process Research & Development 25, no. 12 (2021): 2631–38. http://dx.doi.org/10.1021/acs.oprd.1c00188.

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42

Beck, Barbara, Anne Picard, Eberhardt Herdtweck, and Alexander Dömling. "Highly Substituted Pyrrolidinones and Pyridones by 4-CR/2-CR Sequence." Organic Letters 6, no. 1 (2004): 39–42. http://dx.doi.org/10.1021/ol035787n.

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43

Quertenmont, Mathilde, Iain Goodall, Kevin Lam, István Markó, and Olivier Riant. "Kolbe Anodic Decarboxylation as a Green Way To Access 2-Pyrrolidinones." Organic Letters 22, no. 5 (2020): 1771–75. http://dx.doi.org/10.1021/acs.orglett.0c00056.

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44

Glozman, O. M., L. A. Zhmurenko, V. P. Lezina, et al. "Synthesis and cardiovascular properties of 1-dialkylaminoalkyl-4-aryl-2-pyrrolidinones." Pharmaceutical Chemistry Journal 30, no. 4 (1996): 222–26. http://dx.doi.org/10.1007/bf02218765.

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45

Katkevichs, M., E. Korchagova, T. Ivanova, V. Slavinska, and E. Lukevics. "Selective hydrogenolysis of benzyl-protected 1-hydroxy-3-hydroxyimino-2-pyrrolidinones." Chemistry of Heterocyclic Compounds 42, no. 7 (2006): 872–74. http://dx.doi.org/10.1007/s10593-006-0172-5.

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46

Mickevičius, V., and R. Vaickelioniené. "Condensation products of 1-aryl-4-hydrazinocarbonyl-2-pyrrolidinones with diketones." Chemistry of Heterocyclic Compounds 44, no. 2 (2008): 170–72. http://dx.doi.org/10.1007/s10593-008-0031-7.

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47

Davies, Stephen G., Gilles J. M. Doisneau, Jeremy C. Prodger, and Hitesh J. Sanganee. "Synthesis of 5-substituted-3,3-dimethyl-2-pyrrolidinones: “quat” chiral auxiliaries." Tetrahedron Letters 35, no. 15 (1994): 2369–72. http://dx.doi.org/10.1016/0040-4039(94)85222-7.

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48

Peek, Philip S., and Dana P. McDermott. "Vibrational modes and frequencies of 2-pyrrolidinones and their deutero-isotopomers." Spectrochimica Acta Part A: Molecular Spectroscopy 44, no. 4 (1988): 371–77. http://dx.doi.org/10.1016/0584-8539(88)80058-8.

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49

BRENA-VALLE, L. J., R. CARREON SANCHEZ, and R. CRUZ-ALMANZA. "ChemInform Abstract: Diastereoselective Alkylation of 1-Benzyl-(5S)-Substituted 2- Pyrrolidinones." ChemInform 27, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.199635113.

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50

Roberson, Claudia W., and K. A. Woerpel. "The [3 + 2] Annulation of Allylsilanes and Chlorosulfonyl Isocyanate: Stereoselective Synthesis of 2-Pyrrolidinones." Journal of Organic Chemistry 64, no. 5 (1999): 1434–35. http://dx.doi.org/10.1021/jo982375x.

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