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Journal articles on the topic 'Pyrrolidine derivatives'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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1

Smolobochkin, Andrey V., Almir S. Gazizov, Rakhymzhan A. Turmanov, Dinara S. Abdullaeva, Alexander R. Burilov, and Michail A. Pudovik. "N-Phosphorylated Pyrrolidines: An Overview of Synthetic Approaches." Synthesis 52, no. 15 (2020): 2162–70. http://dx.doi.org/10.1055/s-0039-1690889.

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Organophosphorus pyrrolidine derivatives possessing P–N bonds are a promising yet underexplored class of compounds. In this short review we overview the general approaches to these compounds described so far, with a special emphasis on their asymmetric synthesis.1 Introduction2 Synthesis of Pyrrolidine-Based P(III) Derivatives3 Synthesis of Pyrrolidine-Based P(V) Derivatives3.1 Phosphorylation of Pyrrolidines with P(V) Acid Chlorides3.2 Phosphorylation of Pyrrolidines with P(V) Acid Esters3.3 Syntheses via the Atherton–Todd Reaction3.4 Oxidation of Pyrrolidine-Based P(III) Derivatives4 Synthes

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2

Pfund, Emmanuel, and Thierry Lequeux. "Synthesis of Fluoropyrrolidines and (Fluoroalkyl)pyrrolidines." Synthesis 49, no. 17 (2017): 3848–62. http://dx.doi.org/10.1055/s-0036-1589078.

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Pyrrolidines and their derivatives are of great interest in medicinal chemistry and organic synthesis. Fluoropyrrolidines and (fluoroalkyl)pyrrolidines have been utilized in the preparation of medicinal drugs and also as organocatalysts. The synthesis of such compounds is achieved through the fluorination of pyrrolidine derivatives or by multistep synthesis from already containing fluoroalkyl precursors.1 Introduction1.1 General Interest of Fluorine-Containing Pyrrolidines1.2 Fluoroalkylpyrrolidines and the Gauche Effect2 Fluoropyrrolidines2.1 3-Fluoropyrrolidines2.2 3,3- and 3,4-Difluoropyrro

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3

Sarbu, Laura Gabriela, Catalin Neculai Lungu, Ion Sandu, Paul Chirita, and Lucian Gabriel Bahrin. "Synthesis of 2-Pyrrolydinyl-1,3-Dithiolium Derivatives from Propiophenones." Revista de Chimie 70, no. 4 (2019): 1311–14. http://dx.doi.org/10.37358/rc.19.4.7116.

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Novel bromo-substituted 4-(2-hydroxyaryl)-5-methyl-2-(pyrrolidin-1-yl)-1,3-dithiol-2-ylium perchlorates have been synthesized by the heterocondensation of the corresponding 1-(2-hydroxyaryl)-1-oxopropan-2-yl dithiocarbamates. The latter compounds have been obtained from the reaction of the corresponding substituted a-bromopropiophenones with pyrrolidinium pyrrolidine-1-carbodithioate. The mesoionic 4-(2-pyrrolidinyl-1,3-dithiol-2-ylium-4-yl)phenolates have been obtained from the corresponding 1,3-dithiolium perchlorates under weak basic conditions. These compounds were characterized by NMR and

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4

Zubrickė, Irma, Ilona Jonuškienė, Kristina Kantminienė, Ingrida Tumosienė, and Vilma Petrikaitė. "Synthesis and In Vitro Evaluation as Potential Anticancer and Antioxidant Agents of Diphenylamine-Pyrrolidin-2-one-Hydrazone Derivatives." International Journal of Molecular Sciences 24, no. 23 (2023): 16804. http://dx.doi.org/10.3390/ijms242316804.

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The title compounds were synthesized by the reaction of 5-oxo-1-(4-(phenylamino)phenyl)pyrrolidine-3-carbohydrazide with various aldehydes bearing aromatic and heterocyclic moieties and acetophenones, and their cytotoxicity was tested via MTT assay against human triple-negative breast cancer MDA-MB-231, human melanoma IGR39, human pancreatic carcinoma Panc-1, and prostate cancer cell line PPC-1. Furthermore, the selectivity of compounds towards cancer cells compared to fibroblasts was also investigated. Four compounds were identified as the most promising anticancer agents out of a series of p

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5

Möhrle, Hans, and Johannes Berlitz. "Oxidation 2-substituierter Pyrrolidine und Piperidine als Nicotinanaloga / Oxidation of 2-substituted Pyrrolidines and Piperidines as Nicotine Analogues." Zeitschrift für Naturforschung B 63, no. 8 (2008): 985–92. http://dx.doi.org/10.1515/znb-2008-0811.

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The oxidation of nicotine (1) with Hg(II)-EDTA follows the direction to the α-methylene group of the pyrrolidine part and results in a two-step dehydrogenation to lactam 3. The same course is observed with the aromatic or heteroaromatic 2-substituted compounds 4 - 7 to give the pyrrolidones 8 - 11. In contrast, the 2-methyl- or 2-methylaryl-substituted pyrrolidines 12 - 14 are attacked at the α-methine group with only a two-electron withdrawal and give rise to the iminium derivatives 15 - 17. These salts as well as the corresponding enamines show, after addition of D2O, exchange phenomena in t

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6

Hou, Qinglin, Yaoyao You, Xinluo Song, Yingxia Wang, Ke Chen та Haifei Wang. "Endo-Selective Construction of Spiro-[butyrolactone-pyrrolidine] via Ag(I)/CAAA-Amidphos-Catalyzed 1,3-Dipolar Cycloaddition between Azomethine Ylides and α-Methylene-γ-Butyrolactone". Catalysts 10, № 1 (2019): 28. http://dx.doi.org/10.3390/catal10010028.

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Construction of spirocyclic pyrrolidines bearing a spiro quaternary stereocenter is an enormous challenge in synthetic organic chemistry. In this report, we introduce a Ag(I)/CAAA-amidphos-catalyzed enantioselective 1,3-dipolar cycloaddition between azomethine ylides and α-methylene-γ-butyrolactone as an effective strategy for the construction of excellent endo-selective spiro-[butyrolactone-pyrrolidine] derivatives. Meanwhile, the catalytic system was also successfully applied in the three-component one-pot reaction of azomethine ylides formed in situ under the action of N,N′-diisopropylcarbo

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7

Wang, Yali, Jian Xiao, Aiguo Meng, and Chunyan Liu. "Multivalent Pyrrolidine Iminosugars: Synthesis and Biological Relevance." Molecules 27, no. 17 (2022): 5420. http://dx.doi.org/10.3390/molecules27175420.

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Recently, the strategy of multivalency has been widely employed to design glycosidase inhibitors, as glycomimetic clusters often induce marked enzyme inhibition relative to monovalent analogs. Polyhydroxylated pyrrolidines, one of the most studied classes of iminosugars, are an attractive moiety due to their potent and specific inhibition of glycosidases and glycosyltransferases, which are associated with many crucial biological processes. The development of multivalent pyrrolidine derivatives as glycosidase inhibitors has resulted in several promising compounds that stand out. Herein, we comp

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8

Syal, V. K., U. Becker, R. Elsebrock, and M. Stockhausen. "Dielectric Spectroscopy of Binary Liquid Mixtures of Methanol with Morpholine, Pyrrolidine and some of their Derivatives." Zeitschrift für Naturforschung A 52, no. 8-9 (1997): 675–77. http://dx.doi.org/10.1515/zna-1997-8-921.

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Abstract Dielectric spectra (up to 72 GHz) have been measured at 20 °C for mixtures of methanol and one of the following substances: morpholine, N-methyl morpholine, N-cyano morpholine, pyrrolidine and N-cyano pyrrolidine. The composition dependence of the relaxation parameters shows close similarities for the morpholines and, on the other hand, for the pyrrolidines, which indicates that a structure breaking effect on methanol is exerted by the former but not by the latter group of substances.

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9

Smolobochkin, Andrey, Almir Gazizov, Nurbol Appazov, Oleg Sinyashin, and Alexander Burilov. "Progress in the Stereoselective Synthesis Methods of Pyrrolidine-Containing Drugs and Their Precursors." International Journal of Molecular Sciences 25, no. 20 (2024): 11158. http://dx.doi.org/10.3390/ijms252011158.

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The presented review systematizes and summarizes the data on the synthesis of pyrrolidine derivatives, which are precursors for obtaining drugs. Based on the analysis of published data, the most promising directions in the synthesis of biologically active compounds containing a pyrrolidine ring are identified. Stereoselective synthesis methods are classified based on the source of the pyrrolidine ring. The first group includes methods that use a pyrrolidine ring as the starting compound. The second group combines stereoselective methods of cyclization of acyclic starting compounds, which lead

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10

Betti, Nadia A., Redha Ib Hussain, and Sahar Ab Kadhem. "Synthesis of Some New Derivatives of Pyrrolidine-2-one and Studying Their Antibacterial Potentials." Engineering and Technology Journal 38, no. 3B (2020): 128–41. http://dx.doi.org/10.30684/etj.v38i3b.706.

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New derivatives of pyrrolidine-2-one have been synthesized through lactamization of γ –butyrolactone (GBL) by hydrazine hydrate (80%), ethylene diamine and ethanol amine to afford compounds (1-aminopyrrolidin-2-one), (1-(2-aminoethyl)pyrrolidine-2-one) and (1-(2-hydroxyethyl)pyrrolidine-2-one), respectively. Compound (1-aminopyrrolidin-2-one) underwent several reactions to synthesize the rest of these derivatives. All synthesized compounds were approved by their FT-IR, 1H-NMR and some by Mass spectra. The biological activities of these derivatives were evaluated against Escherichia coli and St

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11

Betti, Nadia A., Redha Ib Hussain, and Sahar Ab Kadhem. "Synthesis of Some New Derivatives of Pyrrolidine-2-one and Studying Their Antibacterial Potentials." Engineering and Technology Journal 38, no. 3B (2020): 128–41. http://dx.doi.org/10.30684/etj.v38i3b.706.

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New derivatives of pyrrolidine-2-one have been synthesized through lactamization of γ –butyrolactone (GBL) by hydrazine hydrate (80%), ethylene diamine and ethanol amine to afford compounds (1-aminopyrrolidin-2-one), (1-(2-aminoethyl)pyrrolidine-2-one) and (1-(2-hydroxyethyl)pyrrolidine-2-one), respectively. Compound (1-aminopyrrolidin-2-one) underwent several reactions to synthesize the rest of these derivatives. All synthesized compounds were approved by their FT-IR, 1H-NMR and some by Mass spectra. The biological activities of these derivatives were evaluated against Escherichia coli and St

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12

Gomes, Ligia R., John Nicolson Low, Fernando Cagide, Alexandra Gaspar, and Fernanda Borges. "A comparison of the structures of some 2- and 3-substituted chromone derivatives: a structural study on the importance of the secondary carboxamide backbone for the inhibitory activity of MAO-B." Acta Crystallographica Section E Crystallographic Communications 71, no. 11 (2015): 1270–77. http://dx.doi.org/10.1107/s2056989015017958.

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The crystal structures of the 3-substituted tertiary chromone carboxamide derivative, C17H13NO3,N-methyl-4-oxo-N-phenyl-4H-chromene-3-carboxamide (1), and the chromone carbonyl pyrrolidine derivatives, C14H13NO3, 3-(pyrrolidine-1-carbonyl)-4H-chromen-4-one (3) and 2-(pyrrolidine-1-carbonyl)-4H-chromen-4-one (4) have been determined. Their structural features are discussed and compared with similar compounds namely with respect to their MAO-B inhibitory activities. The chromone carboxamide presents a –synconformation with the aromatic rings twisted with respect to each other [the dihedral angle

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13

OLIVEIRA, MAILCAR F., TELMA L. G. LEMOS, MARCOS C. DE MATTOS, TACIANA A. SEGUNDO, GILVANDETE M. P. SANTIAGO, and RAIMUNDO BRAZ-FILHO. "New enamine derivatives of lapachol and biological activity." Anais da Academia Brasileira de Ciências 74, no. 2 (2002): 211–21. http://dx.doi.org/10.1590/s0001-37652002000200004.

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A convenient synthesis of the new enamine derivatives 2-(4-morpholinyl)-3-(3-methyl-2-butenyl)-1,4-naphthalenedione, 2-(1-piperidinyl)-3-(3-methyl-2-butenyl)-1,4-naphtalenedione and 2-(1-pyrrolidinyl)-3-(3-methyl-2-butenyl)-1,4-naphthalenedione was carried out from natural 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione (lapachol) and morpholine, piperidine and pyrrolidine. The structures of the products were established mainly by NMR analysis, including 2D experiments. Biological activities of these products were evaluated against Artemia salina, Aedes aegypti and cytotoxicity using A54

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14

Verma, Sharad K., M. Nieves Atanes, J. Hector Busto, Dung L. Thai, and Henry Rapoport. "Hydroxylated Pyrrolidines. Enantiospecific Synthesis ofall-cis2,3,4,5-Substituted Pyrrolidine Derivatives from Serine." Journal of Organic Chemistry 67, no. 4 (2002): 1314–18. http://dx.doi.org/10.1021/jo011008+.

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15

Smetanin, Nikolay, Sofia Tokarieva, Svetlana Varenichenko, Oleg Farat, and Victor Markov. "IN SILICO PREDICTION AND MOLECULAR DOCKING STUDIES OF BIOLOGICAL ACTIVITY OF HYDROACRIDINE (QUINOLINE) DERIVATIVES." Ukrainian Chemistry Journal 87, no. 5 (2021): 38–52. http://dx.doi.org/10.33609/2708-129x.87.05.2021.38-52.

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To find biological activity among easily available 2-[(4S,4’S/4R,4’R)-2’,5’-dioxo-2,3,5,6,7,8-hexahydro-1H-spiro[acridine-4,3’-pyrrolidin]-4’-yl]-N-aryl-acetamide, (4S/4R)-4-[(3R/3S)-1-(2-aryl)-2,5-dioxopyrrolidin-3-yl]-1,2,3,4,5,6,7,8-octahydroacridine-4-carbonitrile, (3S/4R)-3-[(3R/4S)-9-chloroacridine(quinoline)-4-yl]-1-N-aryl)pyrrolidine-2,5-diones. Methods: Organic synthesis, spectral methods, and molecular docking. We investigated by molecular docking the potential biological activity of previously synthesized compounds containing acridine and pyrrolidine-2,5-diones fragments in their st

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16

Song, Qiao, Sheng Wang, Xiangui Lei, Yan Liu, Xin Wen, and Zhouyu Wang. "One-Pot Route from Halogenated Amides to Piperidines and Pyrrolidines." Molecules 27, no. 15 (2022): 4698. http://dx.doi.org/10.3390/molecules27154698.

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Piperidine and pyrrolidine derivatives are important nitrogen heterocyclic structures with a wide range of biological activities. However, reported methods for their construction often face problems of requiring the use of expensive metal catalysts, highly toxic reaction reagents or hazardous reaction conditions. Herein, an efficient route from halogenated amides to piperidines and pyrrolidines was disclosed. In this method, amide activation, reduction of nitrile ions, and intramolecular nucleophilic substitution were integrated in a one-pot reaction. The reaction conditions were mild and no m

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17

Li, Yuqin, Guirong You, Baoxiu Jia, Hongzong Si, and Xiaojun Yao. "Prediction on the Inhibition Ratio of Pyrrolidine Derivatives on Matrix Metalloproteinase Based on Gene Expression Programming." BioMed Research International 2014 (2014): 1–8. http://dx.doi.org/10.1155/2014/210672.

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Quantitative structure-activity relationships (QSAR) were developed to predict the inhibition ratio of pyrrolidine derivatives on matrix metalloproteinase via heuristic method (HM) and gene expression programming (GEP). The descriptors of 33 pyrrolidine derivatives were calculated by the software CODESSA, which can calculate quantum chemical, topological, geometrical, constitutional, and electrostatic descriptors. HM was also used for the preselection of 5 appropriate molecular descriptors. Linear and nonlinear QSAR models were developed based on the HM and GEP separately and two prediction mo

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18

Neumann, Kerstin, Stefan Kehraus, Michael Gütschow, and Gabriele M. König. "Cytotoxic and HLE-Inhibitory Tetramic Acid Derivatives from Marine-Derived Fungi." Natural Product Communications 4, no. 3 (2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400308.

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Tetramic acid derivatives are an important class of nitrogen heterocycles with a pyrrolidine-2,4-dione core as a key structural motif. From the sponge-derived fungus Beauveria bassiana, a new equisetin-like tetramic acid derivative, beauversetin (1), was isolated. The sea weed-derived fungus Microdiplodia sp. produced the tetramic acid derivative 2 (Sch210972) which was shown to inhibit human leucocyte elastase (HLE) with an IC50 of 1.04 μg mL−1.

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Kulak, T. I., D. V. Yankovskaya, A. V. Konoplich, T. N. Buravskaya, and E. N. Kalinichenko. "SYNTHESIS OF NEW 6-N-SUBSTITUTED PURINE NUCLEOSIDES." Proceedings of the National Academy of Sciences of Belarus, Chemical Series 54, no. 3 (2018): 305–13. http://dx.doi.org/10.29235/1561-8331-2018-54-3-305-313.

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New derivatives of purine nucleosides containing the residues of N,N-diethylethylenediamine or N-(2-aminoethyl)pyrrolidine in 6-position of heterobase have been synthesized. The one-step preparation of 6-N-substituted nucleosides was performed in good yields by the amination of 6-Cl-derivatives of O-acetylated purine nucleosides and concomitant deacylation of OH-groups of a carbohydrate moiety with N,N-diethylethylenediamine or N-(2-aminoethyl)pyrrolidine.

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20

Naito, Yuki, Naoki Shida, and Mahito Atobe. "Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor." Beilstein Journal of Organic Chemistry 18 (March 29, 2022): 350–59. http://dx.doi.org/10.3762/bjoc.18.39.

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We have successfully synthesized piperidine and pyrrolidine derivatives by electroreductive cyclization using readily available imine and terminal dihaloalkanes in a flow microreactor. Reduction of the substrate imine on the cathode proceeded efficiently due to the large specific surface area of the microreactor. This method provided target compounds in good yields compared to a conventional batch-type reaction. Furthermore, piperidine and pyrrolidine derivatives could be obtained on preparative scale by continuous electrolysis for approximately 1 hour.

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21

Zhou, Tieli, Xiaofeng Zhang, Desheng Zhan, and Wei Zhang. "Glycine-Based [3+2] Cycloaddition for the Synthesis of Pyrrolidine-Containing Polycyclic Compounds." Molecules 29, no. 23 (2024): 5726. https://doi.org/10.3390/molecules29235726.

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The synthesis of pyrrolidine compounds with biological interest is an active research topic. Glycine could be a versatile starting material for making pyrrolidine derivatives. This review covers recent works on glycine-based [3+2] cycloaddition and combines other annulation reactions in the one-pot synthesis of pyrrolidine-containing heterocyclic compounds. Synthetic method development, substrate scope, and reaction mechanisms are discussed. Applications of the compounds in drug discovery are briefly mentioned. This paper is helpful for chemists in the development of efficient and sustainable

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22

Santalova, Elena A., and Vasily I. Svetashev. "Preparation of 4,4-Dimethyloxazoline and Pyrrolidine Derivatives from Fatty Acid Methyl Esters Using Sodium Borohydride: Mild and Simple One-Pot Derivatization Procedures for a Gas Chromatographic–Mass Spectrometric Analysis of Fatty Acids." Natural Product Communications 17, no. 10 (2022): 1934578X2211314. http://dx.doi.org/10.1177/1934578x221131408.

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Procedures for preparing 4,4-dimethyloxazoline (DMOX) and pyrrolidine derivatives from fatty acid methyl esters (FAMEs) were modified to provide milder and simpler conditions for the derivatization reactions widely used in the mass spectrometric analysis of fatty acids. DMOX and pyrrolidine derivatives were obtained overnight at room temperature in the presence of sodium borohydride. The proposed method, involving a low-temperature condensation-cyclization of FAME to DMOX, allows for the direct preparation of DMOX derivatives from non-hydroxy, 2- and 3-hydroxy acid methyl esters. The described

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23

Lauro, Figueroa‐Valverde, Díaz‐Cedillo Francisco, Rosas‐Nexticapa Marcela, et al. "Synthesis of some pyrrolidine‐2,5‐dione derivatives with biological activity against Gram‐negative bacteria." Vietnam Journal of Chemistry 60, no. 6 (2022): 744–58. http://dx.doi.org/10.1002/vjch.202200028.

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AbstractThere are several methods for the preparation of pyrrolidine‐2,5‐dione analogs, however, some protocols use some reagents which require special conditions such as different pH or higher‐temperatures. The aim of this investigation was to prepare some pyrrolidine‐2,5‐dione derivatives (compounds 4 to 8) from N‐hydroxysuccinimide using some chemical tools to evaluate their biological activity against some bacteria strains. Chemical structure was confirmed with both 1H and 13C NMR spectroscopic techniques. Besides, the effects produced by 4 to 8 on both Gram‐negative and Gram‐positive bact

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24

Kemskiy, Sergiy, Alina Grozav, Sergiy Sujkov, Oleksandr Yurchenko та Mykhailo Vovk. "Pd/C-CATALISED HYDROGENIZATION OF METHYL PYRROLE-3-CARBOXYLATES IN THE DIASTEREOSELECTIVE SYNTHESIS OF α-SUBSTITUTED β-PROLINES". Ukrainian Chemistry Journal 86, № 2 (2020): 100–110. http://dx.doi.org/10.33609/0041-6045.86.2.2020.100-110.

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The analysis of synthetic and biological importance of α-substituted β-prolines was conducted. Methods of synthesis of β-prolines and their esters, based on both intra- and intermolecular reactions of formation of functionalized pyrrolidinic cycle, as well as catalytic reduction of corresponding 2,3-substituted pyrroles and their dihydro derivatives, were systematized. The necessity of the hydrogenation process improvement of 2,3-di-substituted pyrroles using cheap catalysts was justified. The approach to α-substituted β-prolines (2-substituted pyrrolidine-3-carboxylic acids) was pro-posed, th

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Shamsuzzaman, Siddiqui Nazish, and Siddiqui Tabassum. "Synthesis of steroidal enamine - pyrrolidine derivative." Journal of Indian Chemical Society Vol. 81, Nov 2004 (2004): 972–73. https://doi.org/10.5281/zenodo.5833609.

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Department of Chemistry, Aligarh Muslim University, Aligarh-202 002, India <em>Manuscript received 4 December 2003, revised 27 May 2004, accepted 11 June 2004</em> Synthesis or steroidal enamine-pyrrolidine derivative (3) from 3β-acetoxycholest-5-en-7-one (1) and 3β-chlorocholest-5-en-7-one (2) using pyrrolidine is described.

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Kolumbet, Anastasiya Dmitrievna, Mariya Alexandrovna Polovinkina, Margarita Nikolaevna Kolyada, Victoria Pavlovna Osipova, and Konstantin Viktorovich Kudryavtsev. "The effect of pyrrolidine derivatives of 2.6-di-tert-butylphenol on superoxide and hydrogen peroxide-utilization activity of Siberian sturgeon sperm." Vestnik of Astrakhan State Technical University. Series: Fishing industry 2024, no. 4 (2024): 39–46. https://doi.org/10.24143/2073-5529-2024-4-39-46.

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The effect of (3.5-di-tert-butyl-4-hydroxyphenyl)-pyrrolidine-2-carboxylic acid derivatives on the ability of Siberian sturgeon (Acipenser baerii, Brandt, 1869) sperm to utilize superoxide anion radical (O2–•) generated in a model system of adrenaline oxidation in an alkaline medium, as well as exogenous hydrogen peroxide (H2O2) before and after freezing at liquid nitrogen temperature for 3 days was studied. The study of this activity of phenolic derivatives was carried out in comparison with the reference antioxidant Trolox, a water-soluble analogue of vitamin E. When phenolic derivatives wer

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27

Nguyen, Nguyen Tran, Vo Viet Dai, Nguyen Ngoc Tri, Luc Van Meervelt, Nguyen Tien Trung, and Wim Dehaen. "Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones." Beilstein Journal of Organic Chemistry 18 (August 31, 2022): 1140–53. http://dx.doi.org/10.3762/bjoc.18.118.

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Substituted 4-acetyl-3-hydroxy-3-pyrroline-2-ones have been prepared via three-component reactions and the tautomerism of these 3-pyrroline-2-ones is due to the slight difference of energy, and the significantly large rate constant of transformation between two tautomers. 1,4,5-Trisubstituted pyrrolidine-2,3-dione derivatives were prepared from the above mentioned 2-pyrrolidinone derivatives and aliphatic amines, which exist in enamine form and are stabilized by an intramolecular hydrogen bond. A possible reaction mechanism between 3-pyrroline-2-one and aliphatic amine (CH3NH2) was proposed ba

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Matviiuk, Tetiana, Jan Madacki, Giorgia Mori, et al. "Pyrrolidinone and pyrrolidine derivatives: Evaluation as inhibitors of InhA and Mycobacterium tuberculosis." European Journal of Medicinal Chemistry 123 (November 2016): 462–75. http://dx.doi.org/10.1016/j.ejmech.2016.07.028.

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29

SETOI, HIROYUKI, HIROSHI KAYAKIRI, HIDEKAZU TAKENO, and MASASHI HASHIMOTO. "Synthesis of some polyhydroxylated pyrrolidine derivatives." CHEMICAL & PHARMACEUTICAL BULLETIN 35, no. 10 (1987): 3995–99. http://dx.doi.org/10.1248/cpb.35.3995.

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30

Chang, Yuan-Chun, Jiun-Ly Chir, Shuan-Yi Tsai, Wei-Fu Juang, and An-Tai Wu. "Microwave-assisted synthesis of pyrrolidine derivatives." Tetrahedron Letters 50, no. 34 (2009): 4925–29. http://dx.doi.org/10.1016/j.tetlet.2009.06.062.

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31

Basab, Roy, Hatial Ishita, Ghosh Debaki, Sarathi Addy Partha, and Basak Amit. "Synthesis of bicyclic y-lactam derivatives by intramolecular carbene insertion and aza-Wittig reaction." Journal of Indian Chemical Society Vol. 90, Oct 2013 (2013): 1841–51. https://doi.org/10.5281/zenodo.5792069.

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Department of Chemistry, Indian Institute of Technology, Kharagpur-721 302, West Bengal, India <em>E-mail </em>: absk@chem.iitkgp.ernet.in <em>Manuscript received 27 June 2013, accepted 28 June 2013</em> A comparative study of the various methodologies to construct bicyclic \(\gamma\)-lactams is reported. Thus Rh<sup>II</sup> - catalyzed decomposition of 2-pyrrolidone and pyrrolidine derived diazomalonates were attempted to synthesize fused ylactams. Spectral evidences revealed the formation of diastereomeric alcohols instead of desired C-H or N-H insertion products, indicating signi

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Sorokin, Vladimir I., Valery A. Ozeryanskii, Gennady S. Borodkin, Anatoly V. Chernyshev, Max Muir, and Jon Baker. "Preparation of Dialkylamino-Substituted Benzenes and Naphthalenes by Nucleophilic Replacement of Fluorine in the Corresponding Perfluoroaromatic Compounds." Zeitschrift für Naturforschung B 61, no. 5 (2006): 615–25. http://dx.doi.org/10.1515/znb-2006-0519.

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The reactions between hexafluorobenzene (HFB) and octafluoronaphthalene (OFN) with secondary aliphatic amines (pyrrolidine, dimethylamine and piperidine) and lithium amides (pyrrolidide, dimethylamide and piperidide) have been investigated both experimentally and (in part) theoretically. With amines HFB, depending on the selected conditions, gives either di-substituted products or a complex mixture of di-, tri- and tetrasubstituted compounds. Under similar conditions OFN produces almost exclusively the 2,3,6,7-tetrasubstituted compound. Interaction of HFB with the more nucleophilic lithium ami

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33

Almeida, José, Augusto C. Tomé, Maria Rangel, and Ana M. G. Silva. "Microwave-Assisted Synthesis and Spectral Properties of Pyrrolidine-Fused Chlorin Derivatives." Molecules 28, no. 9 (2023): 3833. http://dx.doi.org/10.3390/molecules28093833.

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In this work we pursued research involving the microwave-assisted N-alkylation of a NH pyrrolidine-fused chlorin with methyl 4-(bromomethyl) benzoate and subsequent ester hydrolysis as a straightforward strategy to obtain carboxylic acid functionality in the pyrrolidine-fused chlorin, as a single reaction product. We studied the reaction’s scope by extending the N-alkylation of the free-base chlorin and its corresponding Zn(II) complex to other alkyl halides, including 1,4-diiodobutane, N-(2-bromoethyl)phthalimide, and 2-bromoethanaminium bromide. In addition, two new chlorin–dansyl dyads were

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González, Nieves, Carlos Elvira, and Julio San Román. "Hydrophilic and hydrophobic copolymer systems based on acrylic derivatives of pyrrolidone and pyrrolidine." Journal of Polymer Science Part A: Polymer Chemistry 41, no. 3 (2002): 395–407. http://dx.doi.org/10.1002/pola.10584.

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Gazizov, Almir S., Andrey V. Smolobochkin, Rahimjan A. Turmanov, Michail A. Pudovik, Alexander R. Burilov, and Oleg G. Sinyashin. "Synthesis of Phosphaproline Derivatives: A Short Overview." Synthesis 51, no. 18 (2019): 3397–409. http://dx.doi.org/10.1055/s-0037-1611891.

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Pyrrolidine-based phosphonates, analogues of the natural amino acid proline, possess a diverse set of biological activity. The goal of this short review is to summarize the major developments in the synthesis of phosphaproline derivatives reported since 2004 with special emphasis on the mechanisms and limitations of the methods presented.1 Introduction2 Phosphorylation of Pyrrolidine Derivatives2.1 Syntheses via Pudovik Reaction2.2 Syntheses via Arbuzov Reaction2.3 Decarboxylative Phosphorylation of Proline2.4 Direct C–H Bond Phosphorylation2.5 Other Reactions2.6 Overview of Phosphorylation Me

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36

Izmest’ev, Alexei N., Valentina A. Karnoukhova, Alexander A. Larin, Angelina N. Kravchenko, Leonid L. Fershtat, and Galina A. Gazieva. "Synthesis, Structure and Stereochemistry of Dispirocompounds Based on Imidazothiazolotriazine and Pyrrolidineoxindole." International Journal of Molecular Sciences 23, no. 22 (2022): 13820. http://dx.doi.org/10.3390/ijms232213820.

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Methods for the synthesis of two types of isomeric dispirocompounds based on imidazothiazolotriazine and pyrrolidineoxindole, differing in the structure of imidazothiazolotriazine fragment, namely, linear dispiro[imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine-6,3′-pyrrolidine- 4′,3″-indolines] and angular dispiro[imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine-7,3′-pyrrolidine-4′,3″-indolines] were proposed. The first method relies on a 1,3-dipolar cycloaddition of azomethine ylides generated in situ from paraformaldehyde and N-alkylglycine derivatives to the corresponding oxindolylidene derivative

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37

Guguloth, Rambabu, and Shiva Kumar Gubbiyappa. "Synthesis, Docking and Biological Evaluation of New Series of Pyrrolidine Derivatives as Potent Antibacterial Agents." Asian Journal of Chemistry 36, no. 2 (2024): 489–97. http://dx.doi.org/10.14233/ajchem.2024.31036.

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The chemical flexibility of the pyrrolidine nucleus and its ability to generate a wide range of structural variations may have a significant impact on the therapeutic effectiveness. In present study, 17 analogs of 1-(4-bromo-2-(pyrrolidin-1-yl)benzyl)pyrrolidin-3-amine (7a-q) were synthesized and characterized. All the synthesized compounds were purified by combi-flash chromatography using RediSep RF 1.5 Flash silica gel columns. The synthesized compounds were investigated for antibacterial activity utilizing the agar well diffusion method. Apart from compounds 7l, 7o and 7p, antibacterial act

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Ladeira, Bruno M. F., Cristina J. Dias, Ana T. P. C. Gomes, et al. "Cationic Pyrrolidine/Pyrroline-Substituted Porphyrins as Efficient Photosensitizers against E. coli." Molecules 26, no. 2 (2021): 464. http://dx.doi.org/10.3390/molecules26020464.

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New porphyrin–pyrrolidine/pyrroline conjugates were prepared by revisiting 1,3-dipolar cycloaddition reactions between a porphyrinic azomethine ylide and a series of dipolarophiles. Cationic conjugates obtained by alkylation of the pyrrolidine/pyrroline cycloadducts showed ability to generate singlet oxygen and to produce iodine in presence of KI when irradiated with visible light. Some of the cationic derivatives showed photobactericidal properties towards a Gram-negative bioluminescent E. coli. In all cases, these features were significantly improved using KI as coadjutant, allowing, under t

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Husinec, Suren, Alexander E. A. Porter, and Calum H. Strachan. "Approaches to the synthesis of kainic acid. A study of the synthesis of some 4,5-dihydro-1,2,3-triazoles." Collection of Czechoslovak Chemical Communications 52, no. 1 (1987): 207–14. http://dx.doi.org/10.1135/cccc19870207.

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Kavaliauskas, Povilas, Birutė Sapijanskaitė-Banevič, Birutė Grybaitė, et al. "Synthesis and In Vitro Anticancer Activity of Pyrrolidone Derivatives Bearing 3,4,5-Trimethoxyphenyl Moiety as a Promising Anticancer Scaffold." Applied Sciences 14, no. 24 (2024): 11784. https://doi.org/10.3390/app142411784.

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A series of 5-oxo-1-(3,4,5-trimethoxyphenyl)pyrrolidine-3-carboxylic acid derivatives–hydrazones, N-ethylhydrazones, pyrrole, pyrazole, oxadiazole, and triazole were synthesized and evaluated for their anticancer activity using human A549 pulmonary epithelial cells (ATCC CCl-185). The in vitro viability inhibitory effects of the compounds were assessed using the MTT assay. The characterization of the anticancer activity of the synthesized compounds showed that the incorporation of 1,3,4-oxadiazolethione and 4-aminotriazolethione rings into the molecular structures obviously enhances the antica

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41

Lorente, Antonio, Marta Casillas, Pilar Gomez-Sal, and Antonio Manzanero. "2-Azabuta-1,3-diene-4-carbonitriles: stereoselective synthesis and nucleophilic substitution at the carbon–nitrogen double bond." Canadian Journal of Chemistry 74, no. 3 (1996): 287–94. http://dx.doi.org/10.1139/v96-032.

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The synthesis of (E)-1-methoxy-2-azabuta-1,3-diene-4-carbonitriles was performed by methylation of N-alkenylamides 9 and 11. The Z isomers were obtained by treatment of (E)-1-methylthio-2-azabuta-1,3-diene-4,4-dicarbonitriles with sodium methoxide in methanol. We also describe the reactions of (E)-1-methylthio-2-azabuta-1,3-diene-4,4-dicarbonitriles with pyrrolidine, which afforded 1-(1-pyrrolidinyl) derivatives 20, 21, and 23. X-ray crystallographic analyses of 21 and 23 established the E stereochemistry of the C—N double bond. Key words: 2-azabuta-1,3-diene-4-carbonitriles: stereoselective s

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42

Wu, Yuanqi, Bing Xu, Bing Liu, Zhan-Ming Zhang, and Yu Liu. "A new trifluoromethylated sulfonamide phosphine ligand for Ag(i)-catalyzed enantioselective [3 + 2] cycloaddition of azomethine ylides." Organic & Biomolecular Chemistry 17, no. 6 (2019): 1395–401. http://dx.doi.org/10.1039/c8ob02922a.

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Şener, Şadiye, and Ahmet Mete. "New Phosphorylated Derivatives of Piperidine and Pyrrolidine." Synthetic Communications 27, no. 2 (1997): 307–13. http://dx.doi.org/10.1080/00397919708005033.

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Lu, Xing, Xiaoran He, Lai Feng, Zujin Shi, and Zhennan Gu. "Synthesis of pyrrolidine ring-fused metallofullerene derivatives." Tetrahedron 60, no. 16 (2004): 3713–16. http://dx.doi.org/10.1016/j.tet.2004.02.061.

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45

Chênevert, Robert, Frédéric Jacques, Pascall Giguère, and Mohammed Dasser. "Enzymatic desymmetrization of pyrrolidine and pyrroline derivatives." Tetrahedron: Asymmetry 19, no. 11 (2008): 1333–38. http://dx.doi.org/10.1016/j.tetasy.2008.05.022.

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Nivetha, Narayanasamy, Reshma Mary Martiz, Shashank M. Patil, Ramith Ramu, Swamy Sreenivasa, and Sivan Velmathi. "Benzodioxole grafted spirooxindole pyrrolidinyl derivatives: synthesis, characterization, molecular docking and anti-diabetic activity." RSC Advances 12, no. 37 (2022): 24192–207. http://dx.doi.org/10.1039/d2ra04452h.

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A highly stereoselective, three-component method has been developed for the synthesis of pyrrolidine and pyrrolizidine containing spirooxindole derivatives that exhibits excellent anti-diabetic activity.

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Zhou, Jie, Ming Ji, Haiping Yao, et al. "Discovery of quinazoline-2,4(1H,3H)-dione derivatives as novel PARP-1/2 inhibitors: design, synthesis and their antitumor activity." Organic & Biomolecular Chemistry 16, no. 17 (2018): 3189–202. http://dx.doi.org/10.1039/c8ob00286j.

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48

Deng, Hua, Fu-Sheng He, Cong-Shan Li, Wu-Lin Yang, and Wei-Ping Deng. "Enantioselective construction of tricyclic pyrrolidine-fused benzo[b]thiophene 1,1-dioxide derivatives via copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition." Organic Chemistry Frontiers 4, no. 12 (2017): 2343–47. http://dx.doi.org/10.1039/c7qo00640c.

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A facile Cu(i)-catalyzed asymmetric 1,3-dipolar cycloaddition is developed, affording chiral tricyclic pyrrolidine-fused benzo[b]thiophene derivatives in excellent diastereo- and enantioselectivities.

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Mutra, Mohana Reddy, Vishal Suresh Kudale, Jing Li, Wu-Hsun Tsai, and Jeh-Jeng Wang. "Alkene versus alkyne reactivity in unactivated 1,6-enynes: regio- and chemoselective radical cyclization with chalcogens under metal- and oxidant-free conditions." Green Chemistry 22, no. 7 (2020): 2288–300. http://dx.doi.org/10.1039/d0gc00321b.

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Huang, Ying, Wei Min, Qiu-Wen Wu, Jing Sun, Da-Hua Shi, and Chao-Guo Yan. "Facile one-pot synthesis of spirooxindole-pyrrolidine derivatives and their antimicrobial and acetylcholinesterase inhibitory activities." New Journal of Chemistry 42, no. 19 (2018): 16211–16. http://dx.doi.org/10.1039/c8nj03813a.

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A library of novel spirooxindole-pyrrolidine derivatives were facilely synthesized via 1,3-dipolar cycloaddition of azomethine ylide generated from sarcosine and paraformaldehyde with various 3-methyleneoxindolines.

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