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Journal articles on the topic 'Pyrrolidinone derive'

Author: Grafiati

Published: 4 June 2021

Last updated: 2 February 2022

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1

Benhaoua, Chahrazed, Mustapha Rahmouni, and Hadj Benhaoua. "Diastereoselective Synthesis of some pyrrolidin-2-ones azasugars and study of their stereochemistry." Mediterranean Journal of Chemistry 8, no. 1 (2019): 42–52. http://dx.doi.org/10.13171/mjc8119021922cb.

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The microwave-promoted one-pot multicomponent synthesis of substituted pyrrolidinols using a bifunctional sugar-derived hydroxy-[gamma]-lactone component of amine component or cyanide group is reported. Clean reaction profile, easy work-up procedure, excellent yields and short reaction times are some remarkable features of this method.This modular approach features the in situ-generation of iminium ions intermediate that allows the diastereoselective assembly of the diverse pyrrolidinones efficiently under microwave irradiation has been used.

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2

Beard, Mark J., Jonathan H. Bailey, David T. Cherry, et al. "Functionalised pyrrolidinones derived from (S)-pyroglutamic acid." Tetrahedron 52, no. 10 (1996): 3719–40. http://dx.doi.org/10.1016/0040-4020(96)00047-6.

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3

Wang, Chuan-Chuan, Jing Zhou, Zhi-Wei Ma, Xiao-Pei Chen та Ya-Jing Chen. "Synthesis of spirobarbiturate-pyrrolidinones via a domino aza-Michael/SN2 cyclization of barbiturate-derived alkenes with N-alkoxy α-haloamides". Organic & Biomolecular Chemistry 17, № 41 (2019): 9200–9208. http://dx.doi.org/10.1039/c9ob01992h.

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4

Anwar, Muhammad, Andrew R. Cowley, and Mark G. Moloney. "Novel chiral pyrrolidinone scaffolds derived from threonine with antibacterial activity." Tetrahedron: Asymmetry 21, no. 13-14 (2010): 1758–70. http://dx.doi.org/10.1016/j.tetasy.2010.04.064.

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5

Porter, Michael, Adam Ellwood, Anne Mortimer, and Derek Tocher. "Diastereoselective Thia-Claisen Rearrangement of Pyrrolidinone-Derived KeteneN,S-Acetals." Synlett 2008, no. 14 (2008): 2199–209. http://dx.doi.org/10.1055/s-2008-1078030.

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6

Luker, Tim, Henk Hiemstra, and W. Nico Speckamp. "Synthesis and reactivity of pyrrolidinone- and piperidinone-derived enol triflates." Tetrahedron Letters 37, no. 45 (1996): 8257–60. http://dx.doi.org/10.1016/0040-4039(96)01883-7.

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7

BEARD, M. J., J. H. BAILEY, D. T. CHERRY, et al. "ChemInform Abstract: Functionalized Pyrrolidinones Derived from (S)-Pyroglutamic Acid." ChemInform 27, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199627149.

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8

Edwards, Oliver E., Austin M. Greaves, and Wing-Wah Sy. "Reactions of 1,2-dehydropyrrolidin-5-one with 1,3-dienes. Synthesis of dl-gephyrotoxin 223AB." Canadian Journal of Chemistry 66, no. 5 (1988): 1163–72. http://dx.doi.org/10.1139/v88-191.

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Evidence is presented that the regiospecific and often stereospecific pseudo-Diels–Alder reactions of 1,3-dienes with N-acyl immonium salts, derived from 5-ethoxy-2-pyrrolidinone, are stepwise reactions. 6,7-Dehydroindolizidinones, unsaturated lactam esters, and new indene and furan derivatives are described. A synthesis of dl-gephyrotoxin 223AB (indolizidine 223AB) from trans-1,3-heptadiene was achieved.

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9

Shing, Tony K. M., Kwun W. Wu, Ho T. Wu, and Qicai Xiao. "Syntheses of arabinose-derived pyrrolidine catalysts and their applications in intramolecular Diels–Alder reactions." Organic & Biomolecular Chemistry 13, no. 6 (2015): 1754–62. http://dx.doi.org/10.1039/c4ob02219j.

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10

Xu, Ming-Hui, Yong-Hai Yuan, Dong-Dong Liang, et al. "Remote asymmetric conjugate addition catalyzed by a bifunctional spiro-pyrrolidine-derived thiourea catalyst." Organic Chemistry Frontiers 8, no. 13 (2021): 3292–97. http://dx.doi.org/10.1039/d1qo00238d.

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11

Bailey, Jonathan H., David T. Cherry, Katherine M. Crapnell, et al. "Functionalised pyrrolidinones derived from (S)-pyroglutamic acid by cycloaddition reactions." Tetrahedron 53, no. 34 (1997): 11731–44. http://dx.doi.org/10.1016/s0040-4020(97)00740-0.

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12

Anwar, Muhammed, Jonathan H. Bailey, Laura C. Dickinson, Hermia J. Edwards, Rajesh Goswami, and Mark G. Moloney. "Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues." Org. Biomol. Chem. 1, no. 13 (2003): 2364–76. http://dx.doi.org/10.1039/b303924b.

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13

Chan, Philip W. H., Ian F. Cottrell, and Mark G. Moloney. "Pyrrolidinones derived from (S)-pyroglutamic acid. Part 3. Î²-Aminopyrrolidinones." Journal of the Chemical Society, Perkin Transactions 1, no. 22 (October 25, 2001): 2997–3006. http://dx.doi.org/10.1039/b106782f.

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14

Perry, David, Bracken Roberts, Ginamarie Debevec, Heather Michaels, Debopam Chakrabarti, and Adel Nefzi. "Identification of Bis-Cyclic Guanidines as Antiplasmodial Compounds from Positional Scanning Mixture-Based Libraries." Molecules 24, no. 6 (2019): 1100. http://dx.doi.org/10.3390/molecules24061100.

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The screening of more than 30 million compounds derived from 81 small molecule libraries built on 81 distinct scaffolds identified pyrrolidine bis-cyclic guanidine library (TPI-1955) to be one of the most active and selective antiplasmodial libraries. The screening of the positional scanning library TPI-1955 arranged on four sets of sublibraries (26 + 26 + 26 + 40), totaling 120 samples for testing provided information about the most important groups of each variable position in the TPI-1955 library containing 738,192 unique compounds. The parallel synthesis of the individual compounds derived

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15

Cong, Tiantian, Huamin Wang, Xiuzheng Li, Hai-Hong Wu, and Junliang Zhang. "Chiral bifunctional bisphosphine enabled enantioselective tandem Michael addition of tryptamine-derived oxindoles to ynones." Chemical Communications 55, no. 62 (2019): 9176–79. http://dx.doi.org/10.1039/c9cc04357h.

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A chiral phosphine-catalyzed tandem Michael addition of tryptamine-derived oxindoles to ynones was developed to synthesize spiro[pyrrolidine-3,3′-oxindole] in good yields, good to excellent enantio- and diastereoselectivities.

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16

Davis, Franklin A., He Xu, Yongzhong Wu, and Junyi Zhang. "Asymmetric Synthesis of Polyfunctionalized Pyrrolidines from Sulfinimine-Derived Pyrrolidine 2-Phosphonates. Synthesis of Pyrrolidine 225C." Organic Letters 8, no. 11 (2006): 2273–76. http://dx.doi.org/10.1021/ol060521c.

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17

LUKER, T., H. HIEMSTRA, and W. N. SPECKAMP. "ChemInform Abstract: Synthesis and Reactivity of Pyrrolidinone- and Piperidinone-Derived Enol Triflates." ChemInform 28, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.199707154.

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18

Porter, Michael, Adam Ellwood, Anne Mortimer, and Derek Tocher. "Diastereoselective Thia-Claisen Rearrangement of Pyrrolidinone-Derived [nl]Ketene N,S-Acetals." Synlett 2009, no. 18 (2009): 3052. http://dx.doi.org/10.1055/s-0029-1218336.

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19

Nawaz, Shah, Shiqiang Wei, Yue Huang, Wenyao Wang, Jingping Qu, and Baomin Wang. "Diastereoselective synthesis of indolenine-based spiro[pyrazolone-4,2′-pyrrolidine] scaffolds via 1,3-dipolar cycloaddition of 4-aminopyrazolones, aldehydes, and indolenines." Organic & Biomolecular Chemistry 19, no. 32 (2021): 6964–68. http://dx.doi.org/10.1039/d1ob01135a.

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20

Wang, Cai-Yun, Cheng Dong, Zhan-Jiang Zheng, Zheng Xu, Ke-Fang Yang та Li-Wen Xu. "Construction of an all-substituted pyrrolidine derivative with multiple stereogenic centers and Betti-base-derived γ-amino alcohols by [1,2]-Wittig rearrangement". RSC Advances 5, № 69 (2015): 55819–24. http://dx.doi.org/10.1039/c5ra09145d.

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The construction of Betti base-derived γ-amino alcohols and all-substituted pyrrolidine derivative with multiple stereogenic centers has been developed successfully through neighboring lithium-assisted [1,2]-Wittig rearrangement (NLAWR).

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21

Bailey, Jonathan H., David T. Cherry, James Dyer, et al. "Pyrrolidinones derived from (S )-pyroglutamic acid. Part 1. Conformationally constrained glutamate." Journal of the Chemical Society, Perkin Transactions 1, no. 16 (2000): 2783–92. http://dx.doi.org/10.1039/b001999m.

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22

Chan, Philip W. H., Ian F. Cottrell, and Mark G. Moloney. "Pyrrolidinones derived from (S)-pyroglutamic acid. Part 4. Î±, Î²-Diaminopyrrolidinones." Journal of the Chemical Society, Perkin Transactions 1, no. 22 (October 25, 2001): 3007–12. http://dx.doi.org/10.1039/b106783b.

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23

White, James F., Johnathan E. Holladay, Allan A. Zacher, John G. Frye, and Todd A. Werpy. "Challenges in Catalytic Manufacture of Renewable Pyrrolidinones from Fermentation Derived Succinate." Topics in Catalysis 57, no. 17-20 (2014): 1325–34. http://dx.doi.org/10.1007/s11244-014-0299-z.

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24

Velasco, Diego, Carlos Elvira, and Julio San Román. "New stimuli-responsive polymers derived from morpholine and pyrrolidine." Journal of Materials Science: Materials in Medicine 19, no. 4 (2007): 1453–58. http://dx.doi.org/10.1007/s10856-007-3315-z.

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25

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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26

Back, Thomas G., Scott Collins та Kwok-Wai Law. "Reactions of amines with β-(phenylseleninyl)vinyl sulfones derived from the selenosulfonation of acetylenes. Formation of enamine sulfones". Canadian Journal of Chemistry 63, № 8 (1985): 2313–18. http://dx.doi.org/10.1139/v85-382.

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β-(Phenylseleno)vinyl sulfones 2 were prepared from the selenosulfonation of acetylenes and were oxidized to the corresponding selenoxides 3. These were treated insitu with morpholine (4) or pyrrolidine (5) to afford the corresponding enamine sulfones 6 and, in those cases where 3 were derived from terminal acetylenes, their selenenylated analogues 7. The formation of the latter was enhanced by adding benzeneselenenyl chloride to the reaction mixture, and suppressed by the presence of selenenic acid scavengers such as enamine 10 or ethyl vinyl ether. In several instances the enamine sulfones w

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27

Abd-El-Aziz, Alaa S., Adam Piórko, Choi Chuck Lee, and Ronald G. Sutherland. "Studies on some selective and competitive substitution reactions of cyclopentadienyliron complexed chloronitrobenzenes with amines as nucleophiles." Canadian Journal of Chemistry 67, no. 10 (1989): 1618–23. http://dx.doi.org/10.1139/v89-247.

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Nucleophilic substitution reactions of the (η6-o-, -m-, or -p-chloronitrobenzene)(η5-cyclopentadienyl)iron cation (2a, 2b, or 2c, respectively) with aniline, n-butylamine, or pyrrolidine as nucleophile were investigated. It was found that only selective displacement of the nitro group occurred for reactions with aniline. For reaction with n-butylamine or pyrrolidine, o-isomer 2a resulted in the selective displacement of only the chloro group, giving rise to the (η6-o-n-butylaminonitrobenzene)(η5-cyclo-pentadienyl)iron cation (5a) or the (η6-o-nitro-N-pyrrolidinylbenzene)(η5-cyclopentadienyl)ir

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28

BAILEY, J. H., D. T. CHERRY, K. M. CRAPNELL, et al. "ChemInform Abstract: Functionalized Pyrrolidinones Derived from (S)-Pyroglutamic Acid by Cycloaddition Reactions." ChemInform 29, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199801122.

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29

Chan, Philip W. H., Ian F. Cottrell та Mark G. Moloney. "ChemInform Abstract: Pyrrolidinones Derived from (S)-Pyroglutamic Acid. Part 3. β-Aminopyrrolidinones." ChemInform 33, № 13 (2010): no. http://dx.doi.org/10.1002/chin.200213190.

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30

Dyer, James, Amanda King, Steve Keeling, and Mark G. Moloney. "Pyrrolidinones derived from (S )-pyroglutamic acid. Part 2. Conformationally constrained kainoid analogues." Journal of the Chemical Society, Perkin Transactions 1, no. 16 (2000): 2793–804. http://dx.doi.org/10.1039/b002001j.

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31

Yeong, Mee Ling, Simon P. Clark, Julie M. Waring, Raymond D. Wilson, and St John Wakefield. "The effects of comfrey derived pyrrolidine alkaloids on rat liver." Pathology 23, no. 1 (1991): 35–38. http://dx.doi.org/10.3109/00313029109061438.

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32

Slobodyanyuk, Evgeniy Y., Oleksiy S. Artamonov, Irene B. Kulik, Eduard Rusanov, Dmitriy M. Volochnyuk, and Oleksandr O. Grygorenko. "A bio-inspired approach to proline-derived 2,4-disubstituted oxazoles." Heterocyclic Communications 24, no. 1 (2018): 11–17. http://dx.doi.org/10.1515/hc-2017-0235.

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Abstract A convenient four-step approach to the synthesis of (S)-4-alkyl-2-(pyrrolidin-2-yl)oxazoles starting from l-Boc-proline inspired by naturally occurring oxazole-containing peptidomimetics is described. The key step is the cyclization of 1-Boc-N-(1-oxoalkan-2-yl)pyrrolidine-2-carboxamides – aldehyde intermediates which demonstrate low to moderate stability – under Appel reaction conditions. This method furnishes the target compounds with more than 98% ee and in a 17–51% overall yield and has been used at up to a 45-g scale.

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33

Royer, Jacques, Armand Blommaert, Philippe James, Fanny Valleix, and Henri-Philippe Husson. "Mono and Sequential Bis Solid Phase Alkylations of a (R)-Phenylglycinol Derived Pyrrolidinone Scaffold." HETEROCYCLES 55, no. 12 (2001): 2273. http://dx.doi.org/10.3987/com-01-9350.

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34

Liu, Xiong-Li, Dong-Gui Guo, Zheng Li, Xiao-Xue Han, Lei Zhang, and Min Zhang. "Decarboxylative, Diastereoselective and exo-Selective 1,3-Dipolar Cycloaddition for Diversity-Oriented Construction of Structural Spiro[Butyrolactone–Pyrrolidine–Chromanone] Hybrids." Synlett 32, no. 14 (2021): 1447–52. http://dx.doi.org/10.1055/a-1535-8891.

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AbstractInspired by the chemistry and biology of butyrolactones, pyrrolidines, and chromanones, we successfully developed a simple domino 1,3-dipolar cycloaddition of homoserine-lactone-derived azomethine ylides for the construction of biologically important spiro[butyrolactone–pyrrolidine–chromanone] hybrids in the presence of Et3N as a catalyst under mild conditions. The reaction is based on the application of carboxylic-acid-activated chromones as dienophiles, followed by a decarboxylation process. This reaction displayed good substrate tolerance and gave the desired products in moderate to

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35

Szcześniak, Piotr, Barbara Grzeszczyk, and Bartłomiej Furman. "A Convenient Approach towards the Synthesis of ADMDP Type Iminosugars and Nojirimycin Derivatives from Sugar-Derived Lactams." Molecules 26, no. 18 (2021): 5459. http://dx.doi.org/10.3390/molecules26185459.

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An efficient method for the synthesis of nojirimycin- and pyrrolidine-based iminosugar derivatives has been developed. The strategy is based on the partial reduction in sugar-derived lactams by Schwartz’s reagent and tandem stereoselective nucleophilic addition of cyanide or a silyl enol ether dictated by Woerpel’s or diffusion control models, which affords amino-modified iminosugars, such as ADMDP or higher nojirimycin derivatives.

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36

Bailey, Jonathan H., David T. Cherry, James Dyer, et al. "ChemInform Abstract: Pyrrolidinones Derived from (S)-Pyroglutamic Acid. Part 1. Conformationally Constrained Glutamate." ChemInform 31, no. 51 (2000): no. http://dx.doi.org/10.1002/chin.200051030.

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37

Chan, Philip W. H., Ian F. Cottrell та Mark G. Moloney. "ChemInform Abstract: Pyrrolidinones Derived from (S)-Pyroglutamic Acid. Part 4. α,β-Diaminopyrrolidinones." ChemInform 33, № 11 (2010): no. http://dx.doi.org/10.1002/chin.200211097.

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38

KONG, R., X. XU, W. CHEN, C. WANG, and L. HU. "Pharmacophore Model Generation Based on Pyrrolidine- and Butane-derived CCR5 Antagonists." Acta Physico-Chimica Sinica 23, no. 9 (2007): 1325–31. http://dx.doi.org/10.1016/s1872-1508(07)60067-9.

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39

Velasco, D., E. Collin, J. San Roman, A. Pandit, and C. Elvira. "End functionalized polymeric system derived from pyrrolidine provide high transfection efficiency." European Journal of Pharmaceutics and Biopharmaceutics 79, no. 3 (2011): 485–94. http://dx.doi.org/10.1016/j.ejpb.2011.06.004.

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40

Castán, Alejandro, Ramón Badorrey, José A. Gálvez, and María D. Díaz-de-Villegas. "Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins." Beilstein Journal of Organic Chemistry 13 (March 27, 2017): 612–19. http://dx.doi.org/10.3762/bjoc.13.59.

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New pyrrolidine-based organocatalysts with a bulky substituent at C2 were synthesized from chiral imines derived from (R)-glyceraldehyde acetonide by diastereoselective allylation followed by a sequential hydrozirconation/iodination reaction. The new compounds were found to be effective organocatalysts for the Michael addition of aldehydes to nitroolefins and enantioselectivities up to 85% ee were achieved.

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41

West, Robert. "The deadly weed: Nicotine and tobacco dependence." Biochemist 24, no. 5 (2002): 15–17. http://dx.doi.org/10.1042/bio02405015.

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Nicotine is an alkaloid that is derived exclusively from the plants of the tobacco family. Of its two isomers, S-nicotine is by far the most common and biologically potent, and the much rarer R-nicotine has only a weak biological activity. Nicotine has a simple structure that consists of a pyridine and pyrrolidine ring (Figure 1).

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42

Dyer, James, Amanda King, Steve Keeling, and Mark G. Moloney. "ChemInform Abstract: Pyrrolidinones Derived from (S-)-Pyroglutamic Acid. Part 2. Conformationally Constrained Kainoid Analogues." ChemInform 31, no. 51 (2000): no. http://dx.doi.org/10.1002/chin.200051031.

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43

Comanita, Eugenia, Gheorghe Roman, Irina Popovici, and Bogdan Comanita. "Synthesis and reactivity of some mannich bases. VIII. Studies on several mannich bases derived from ortho-hidroxyacetophenones and their conversion into oximino derivatives." Journal of the Serbian Chemical Society 66, no. 1 (2001): 9–16. http://dx.doi.org/10.2298/jsc0101009c.

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The synthesis of several Mannich bases resulting from the reaction of 2-hydroxy-4-methylacetophenone with paraformaldehyde and secondary amines is reported. Another series of products was obtained from N,N-dimethyl substituted Mannich bases by replacing the amino group with pyrrolidine. Most of the Mannich bases were transformed into oximes by treatment with hydroxylamine hydrochloride in 10% NaOH.

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44

Wang, Zhen, Weijun Yao, Xiangsheng Cheng, Weihong Fei, Zihao Luo та Jianjun Li. "DABCO-Catalyzed α-Regio- and Diastereoselective (3+2) Cycloadditions of Nitrone Ylides from Isatins and Activated Alkenes". Synthesis 52, № 23 (2020): 3632–39. http://dx.doi.org/10.1055/s-0040-1707352.

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α-Regio- and diastereoselective (3+2) cycloadditions of nitrone ylides derived from isatins with activated alkenes have been demonstrated. This mild protocol allows rapid access to a wide range of 3′,5′-diaryl-1′-hydroxy-2-oxospiro[indoline-3,2′-pyrrolidine] derivatives by using DABCO as an efficient catalyst. This method could also be carried out through three-component reaction efficiently in good yields and excellent diastereoselectivity.

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45

ApSimon, J. W., L. W. Herman, and C. Huber. "The synthesis of 5-hydroxy chromenes." Canadian Journal of Chemistry 63, no. 10 (1985): 2589–96. http://dx.doi.org/10.1139/v85-430.

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The synthesis of 2,2-dimethyl-5-hydroxychromene (1d) is described. The synthesis of the analogous 5,7-dihydroxy derivatives, using similar conditions, yields the adduct 9 derived via a Bucherer type reaction. X-ray analysis of 9 demonstrated that a pyrrolidine group was in the 7-position, and that the 5-hydroxyl group was involved in a strong intramolecular hydrogen bond to the 4-keto oxygen atom.

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46

Jiang, Minghua, Senhua Chen, Jing Li, and Lan Liu. "The Biological and Chemical Diversity of Tetramic Acid Compounds from Marine-Derived Microorganisms." Marine Drugs 18, no. 2 (2020): 114. http://dx.doi.org/10.3390/md18020114.

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Tetramic acid (pyrrolidine-2,4-dione) compounds, isolated from a variety of marine and terrestrial organisms, have attracted considerable attention for their diverse, challenging structural complexity and promising bioactivities. In the past decade, marine-derived microorganisms have become great repositories of novel tetramic acids. Here, we discuss the biological activities of 277 tetramic acids of eight classifications (simple 3-acyl tetramic acids, 3-oligoenoyltetramic acids, 3-decalinoyltetramic acid, 3-spirotetramic acids, macrocyclic tetramic acids, N-acylated tetramic acids, α-cyclopia

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47

Nanda, Kausik K., and B. Wesley Trotter. "Diastereoselective Petasis Mannich reactions accelerated by hexafluoroisopropanol: a pyrrolidine-derived arylglycine synthesis." Tetrahedron Letters 46, no. 12 (2005): 2025–28. http://dx.doi.org/10.1016/j.tetlet.2005.01.151.

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48

Liu, Hong-Bing, RuAngelie Edrada-Ebel, Rainer Ebel, et al. "Ophiobolin Sesterterpenoids and Pyrrolidine Alkaloids from the Sponge-Derived Fungus Aspergillus ustus." Helvetica Chimica Acta 94, no. 4 (2011): 623–31. http://dx.doi.org/10.1002/hlca.201000283.

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49

Tsuda, Masashi, Mai Sasaki, Takao Mugishima, et al. "Scalusamides A−C, New Pyrrolidine Alkaloids from the Marine-Derived FungusPenicillium citrinum." Journal of Natural Products 68, no. 2 (2005): 273–76. http://dx.doi.org/10.1021/np049661q.

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50

Armstrong, Alan, Ghafoor Ahmed, Ian Garnett, and Katell Goacolou. "Pyrrolidine-Derived Iminium Salts as Catalysts for Alkene Epoxidation by Oxone®." Synlett 1997, no. 9 (1997): 1075–76. http://dx.doi.org/10.1055/s-1997-1542.

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