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Journal articles on the topic 'Carbamoyl radicals'

Author: Grafiati

Published: 25 January 2025

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1

Safiulina, A. M., A. V. Lizunov, E. I. Goryunov, G. V. Bodrin, I. B. Goryunova, T. V. Strelkova, M. S. Grigor'ev, V. K. Brel', and I. G. Tananaev. "Derivatives of (2-carbamoyl ethyl)diphenylphosphine oxides: synthesis and extraction properties with respect to actinides and lanthanides." Журнал неорганической химии 69, no. 1 (January 15, 2024): 99–109. http://dx.doi.org/10.31857/s0044457x24010124.

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A series of (2–carbamoyl ethyl)diphenylphosphine oxides (KFO) has been synthesized from commercially available reagents — diphenyl chlorophosphine and acrylamides. The influence of the number of ligand fragments of Ph2P(O)(CH2)2C(O), the nature of the oligoyl radical binding these fragments, as well as the presence of additional coordination centers in the KEFO molecule on the extraction properties of KEFO with respect to actinides and lanthanides was investigated. It was found that N,N′-methylene-bis[3-(diphenylphosphoryl) has the greatest efficiency in the extraction of actinidespropionamide] (III), in which two diphenylphosphorylpropionyl radicals are bound by a rigid HNCH2NH linker (the degree of extraction of U(VI) reaches ~73%, and Th(IV) — ~85%), while in the case of lanthanides, on the contrary, ligand V, containing the maximum amount of this kind of phosphoryl carbonyl radicals attached to a conformationally non-rigid nitrogenous heterocyclic matrix, as well as KEFO (II), containing an additional C=O group in an alkyl radical attached to a nitrogen atom, has significant advantages carbamoyl fragment (when using this compound, gadolinium extraction is close to 92%). The obtained data show that highly effective and selective extractants of both 4fand 5felements can be created on the basis of (2-carbamoyl ethyl)diphenylphosphine oxide structure.

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2

Raviola, Carlotta, Stefano Protti, Davide Ravelli, and Maurizio Fagnoni. "Photogenerated acyl/alkoxycarbonyl/carbamoyl radicals for sustainable synthesis." Green Chemistry 21, no. 4 (2019): 748–64. http://dx.doi.org/10.1039/c8gc03810d.

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3

Xie, Long-Yong, Sha Peng, Li-Hua Yang, and Xiao-Wen Liu. "Metal-Free Synthesis of Carbamoylated Chroman-4-Ones via Cascade Radical Annulation of 2-(Allyloxy)arylaldehydes with Oxamic Acids." Molecules 27, no. 20 (October 19, 2022): 7049. http://dx.doi.org/10.3390/molecules27207049.

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An efficient and straightforward approach for the synthesis of carbamoylated chroman-4-ones has been well-developed. The reaction is triggered through the generation of carbamoyl radicals from oxamic acids under metal-free conditions, which subsequently undergoes decarboxylative radical cascade cyclization on 2-(allyloxy)arylaldehydes to afford various amide-containing chroman-4-one scaffolds with high functional group tolerance and a broad substrate scope.

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4

de Pedro Beato, Eduardo, Daniele Mazzarella, Matteo Balletti, and Paolo Melchiorre. "Photochemical generation of acyl and carbamoyl radicals using a nucleophilic organic catalyst: applications and mechanism thereof." Chemical Science 11, no. 24 (2020): 6312–24. http://dx.doi.org/10.1039/d0sc02313b.

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An organic catalyst uses low-energy photons to generate acyl and carbamoyl radicals upon activation of the corresponding chlorides via a nucleophilic acyl substitution path. The synthetic potential and the mechanism of this strategy are discussed.

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5

Osmanoğlua, Şemsettin, Murat Aydın, and M. Halim Başkana. "EPR of Gamma-irradiated L-Glutamine Hydrochloride and N-Carbamoyl-L-glutamic Acid." Zeitschrift für Naturforschung A 60, no. 7 (July 1, 2005): 549–53. http://dx.doi.org/10.1515/zna-2005-0715.

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The electron paramagnetic resonance spectra of γ -irradiated L-glutamine hydrochloride and N-carbamoyl- L-glutamic acid single crystals have been investigated at room temperature. Radiation damage centres are attributed to ĊH, ṄH2 and CH2Ċ(NH2)COOH radicals.

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6

Rigby, James H., Diana M. Danca, and John H. Horner. "Carbamoyl radicals from Se-phenylselenocarbamates: Intramolecular additions to alkenes." Tetrahedron Letters 39, no. 46 (November 1998): 8413–16. http://dx.doi.org/10.1016/s0040-4039(98)01830-9.

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7

Song, Liyan, Xinqiang Fang, Zijia Wang, Kun Liu, and Chaozhong Li. "Stereoselectivity of 6-Exo Cyclization of α-Carbamoyl Radicals." Journal of Organic Chemistry 81, no. 6 (March 7, 2016): 2442–50. http://dx.doi.org/10.1021/acs.joc.6b00008.

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8

Song, Liyan, Kun Liu, and Chaozhong Li. "Efficient and Regioselective 9-EndoCyclization of α-Carbamoyl Radicals." Organic Letters 13, no. 13 (July 2011): 3434–37. http://dx.doi.org/10.1021/ol201180g.

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9

Minisci, Francesco, Fausta Coppa, and Francesca Fontana. "Reactivity of carbamoyl radicals: the first general and convenient free-radical synthesis of isocyanates." Journal of the Chemical Society, Chemical Communications, no. 6 (1994): 679. http://dx.doi.org/10.1039/c39940000679.

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10

Koshiishi, Ichiro, Kazunori Tsuchida, Tokuko Takajo, and Makiko Komatsu. "Radical scavenger can scavenge lipid allyl radicals complexed with lipoxygenase at lower oxygen content." Biochemical Journal 395, no. 2 (March 28, 2006): 303–9. http://dx.doi.org/10.1042/bj20051595.

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Lipoxygenases have been proposed to be a possible factor that is responsible for the pathology of certain diseases, including ischaemic injury. In the peroxidation process of linoleic acid by lipoxygenase, the E,Z-linoleate allyl radical–lipoxygenase complex seems to be generated as an intermediate. In the present study, we evaluated whether E,Z-linoleate allyl radicals on the enzyme are scavenged by radical scavengers. Linoleic acid, the content of which was greater than the dissolved oxygen content, was treated with soya bean lipoxygenase-1 (ferric form) in the presence of radical scavenger, CmP (3-carbamoyl-2,2,5,5-tetramethylpyrrolidine-N-oxyl). The reaction rate between oxygen and lipid allyl radical is comparatively faster than that between CmP and lipid allyl radical. Therefore a reaction between linoleate allyl radical and CmP was not observed while the dioxygenation of linoleic acid was ongoing. After the dissolved oxygen was depleted, CmP stoichiometrically trapped linoleate-allyl radicals. Accompanied by this one-electron redox reaction, the resulting ferrous lipoxygenase was re-oxidized to the ferric form by hydroperoxylinoleate. Through the adduct assay via LC (liquid chromatography)–MS/MS (tandem MS), four E,Z-linoleate allyl radical–CmP adducts corresponding to regio- and diastereo-isomers were detected in the linoleate/lipoxygenase system, whereas E,E-linoleate allyl radical–CmP adducts were not detected at all. If E,Z-linoleate allyl radical is liberated from the enzyme, the E/Z-isomer has to reach equilibrium with the thermodynamically favoured E/E-isomer. These data suggested that the E,Z-linoleate allyl radicals were not liberated from the active site of lipoxygenase before being trapped by CmP. Consequently, we concluded that the lipid allyl radicals complexed with lipoxygenase could be scavenged by radical scavengers at lower oxygen content.

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11

Panagopoulos, Anastasios, Konstantina Alipranti, Kyriaki Mylona, Polinikis Paisidis, Stergios Rizos, Alexandros E. Koumbis, Emmanouil Roditakis, and Konstantina C. Fylaktakidou. "Exploration of the DNA Photocleavage Activity of O-Halo-phenyl Carbamoyl Amidoximes: Studies of the UVA-Induced Effects on a Major Crop Pest, the Whitefly Bemisia tabaci." DNA 3, no. 2 (April 4, 2023): 85–100. http://dx.doi.org/10.3390/dna3020006.

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The DNA photocleavage effect of halogenated O-carbamoyl derivatives of 4-MeO-benzamidoxime under UVB and UVA irradiation was studied in order to identify the nature, position, and number of halogens on the carbamoyl moiety that ensure photoactivity. F, Cl, and Br-phenyl carbamate esters (PCME) exhibited activity with the p-Cl-phenyl derivative to show excellent photocleavage against pBR322 plasmid DNA. m-Cl-PCME has diminished activity, whereas the presence of two halogen atoms reduced DNA photocleavage. The substitution on the benzamidoxime scaffold was irrelevant to the activity. The mechanism of action indicated function in the absence of oxygen, probably via radicals derived from the N-O bond homolysis of the carbamates and in air via hydroxyl radicals and partially singlet oxygen. The UVA-vis area of absorption of the nitro-benzamidoxime p-Cl-PCMEs allowed for the investigation of their potential efficacy as photopesticides under UVA irradiation against the whitefly Bemisia tabaci, a major pest of numerous crops. The m-nitro derivative exhibited a moderate specificity against the adult population. Nymphs were not affected. The compound was inactive in the dark. This result may allow for the development of lead compounds for the control of agricultural insect pests that can cause significant economic damage in crop production.

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12

López-Valdez, Germán, Simón Olguín-Uribe, and Luis D. Miranda. "Carbamoyl radicals from carbamoylxanthates: a facile entry into isoindolin-1-ones." Tetrahedron Letters 48, no. 47 (November 2007): 8285–89. http://dx.doi.org/10.1016/j.tetlet.2007.09.142.

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13

RIGBY, J. H., D. M. DANCA, and J. H. HORNER. "ChemInform Abstract: Carbamoyl Radicals from Se-Phenylselenocarbamates: Intramolecular Additions to Alkenes." ChemInform 30, no. 6 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199906150.

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14

MINISCI, F., F. COPPA, and F. FONTANA. "ChemInform Abstract: Reactivity of Carbamoyl Radicals: The First General and Convenient Free-Radical Synthesis of Isocyanates." ChemInform 25, no. 31 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199431121.

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15

Assayag, Miri, Sara Goldstein, Amram Samuni, and Neville Berkman. "3-Carbamoyl-proxyl nitroxide radicals attenuate bleomycin-induced pulmonary fibrosis in mice." Free Radical Biology and Medicine 171 (August 2021): 135–42. http://dx.doi.org/10.1016/j.freeradbiomed.2021.05.010.

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16

Song, Liyan, Kun Liu, and Chaozhong Li. "ChemInform Abstract: Efficient and Regioselective 9-endo Cyclization of α-Carbamoyl Radicals." ChemInform 42, no. 45 (October 13, 2011): no. http://dx.doi.org/10.1002/chin.201145167.

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17

Grainger, Richard S., and Paolo Innocenti. "Dithiocarbamate Group Transfer Cyclization Reactions of Carbamoyl Radicals under “Tin-Free” Conditions." Angewandte Chemie International Edition 43, no. 26 (June 28, 2004): 3445–48. http://dx.doi.org/10.1002/anie.200453600.

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18

Grainger, Richard S., and Paolo Innocenti. "Dithiocarbamate Group Transfer Cyclization Reactions of Carbamoyl Radicals under“Tin-Free” Conditions." Angewandte Chemie 116, no. 26 (June 28, 2004): 3527–30. http://dx.doi.org/10.1002/ange.200453600.

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19

Cardinale, Luana, Mikhail O. Konev, and Axel Jacobi von Wangelin. "Photoredox‐Catalyzed Addition of Carbamoyl Radicals to Olefins: A 1,4‐Dihydropyridine Approach." Chemistry – A European Journal 26, no. 37 (June 11, 2020): 8239–43. http://dx.doi.org/10.1002/chem.202002410.

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20

Franco Bella, A., Leon V. Jackson, and John C. Walton. "Preparation of β-and γ-lactams via ring closures of unsaturated carbamoyl radicals derived from 1-carbamoyl-1-methylcyclohexa-2,5-dienes." Org. Biomol. Chem. 2, no. 3 (2004): 421–28. http://dx.doi.org/10.1039/b313932h.

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21

Minisci, Francesco, Francesca Fontana, Fausta Coppa, and Yong Ming Yan. "Reactivity of Carbamoyl Radicals. A New, General, Convenient Free-Radical Synthesis of Isocyanates from Monoamides of Oxalic Acid." Journal of Organic Chemistry 60, no. 17 (September 1995): 5430–33. http://dx.doi.org/10.1021/jo00122a020.

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22

Scanlan, Eoin M., Alexandra M. Z. Slawin, and John C. Walton. "Preparation of β- and γ-lactams from carbamoyl radicals derived from oxime oxalate amides." Org. Biomol. Chem. 2, no. 5 (2004): 716–24. http://dx.doi.org/10.1039/b315223e.

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23

Kovacic, Peter. "Hydroxyurea (therapeutics and mechanism): Metabolism, carbamoyl nitroso, nitroxyl, radicals, cell signaling and clinical applications." Medical Hypotheses 76, no. 1 (January 2011): 24–31. http://dx.doi.org/10.1016/j.mehy.2010.08.023.

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24

MINISCI, F., F. FONTANA, F. COPPA, and Y. M. YAN. "ChemInform Abstract: Reactivity of Carbamoyl Radicals. A New, General, Convenient Free- Radical Synthesis of Isocyanates from Monoamides of Oxalic Acid." ChemInform 27, no. 1 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199601091.

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25

Fang, Xinqiang, Kun Liu, and Chaozhong Li. "Efficient Regio- and Stereoselective Formation of Azocan-2-ones via 8-EndoCyclization of α-Carbamoyl Radicals." Journal of the American Chemical Society 132, no. 7 (February 24, 2010): 2274–83. http://dx.doi.org/10.1021/ja9082649.

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26

Fujiwara, Shin-ichi, Yoshihiko Shimizu, Yuji Imahori, Masashi Toyofuku, Tsutomu Shin-ike, and Nobuaki Kambe. "A new entry to α-alkylidene-β-lactams by 4-exo-dig cyclization of carbamoyl radicals." Tetrahedron Letters 50, no. 26 (July 2009): 3628–30. http://dx.doi.org/10.1016/j.tetlet.2009.03.071.

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27

DiLabio, Gino A., Eoin M. Scanlan, and John C. Walton. "Kinetic and Theoretical Study of 4-exoRing Closures of Carbamoyl Radicals onto CC and CN Bonds." Organic Letters 7, no. 1 (January 2005): 155–58. http://dx.doi.org/10.1021/ol047716+.

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28

Benati, Luisa, Giorgio Bencivenni, Rino Leardini, Matteo Minozzi, Daniele Nanni, Rosanna Scialpi, Piero Spagnolo, and Giuseppe Zanardi. "Generation and Cyclization of Unsaturated Carbamoyl Radicals Derived fromS-4-Pentynyl Carbamothioates under Tin-Free Conditions." Journal of Organic Chemistry 71, no. 8 (April 2006): 3192–97. http://dx.doi.org/10.1021/jo0602064.

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29

Liu, Li, Qian Chen, Yun-Dong Wu, and Chaozhong Li. "8-Endo versus 7-Exo Cyclization of α-Carbamoyl Radicals. A Combination of Experimental and Theoretical Studies." Journal of Organic Chemistry 70, no. 5 (March 2005): 1539–44. http://dx.doi.org/10.1021/jo0481349.

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30

Quirante, Josefina, Carmen Escolano, Laura Costejà, and Josep Bonjoch. "Cyclization of 1-(carbamoyl)dichloromethyl radicals upon activated alkenes. A new entry to 2-azabicyclo[3.3.1]nonanes." Tetrahedron Letters 38, no. 39 (September 1997): 6901–4. http://dx.doi.org/10.1016/s0040-4039(97)01590-6.

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31

Francisco, Cosme G., Antonio J. Herrera, Ángeles Martín, Inés Pérez-Martín, and Ernesto Suárez. "Intramolecular 1,5-hydrogen atom transfer reaction promoted by phosphoramidyl and carbamoyl radicals: synthesis of 2-amino-C-glycosides." Tetrahedron Letters 48, no. 36 (September 2007): 6384–88. http://dx.doi.org/10.1016/j.tetlet.2007.06.152.

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32

Bai, Qi-Fan, Chengan Jin, Jing-Yao He, and Gaofeng Feng. "Carbamoyl Radicals via Photoredox Decarboxylation of Oxamic Acids in Aqueous Media: Access to 3,4-Dihydroquinolin-2(1H)-ones." Organic Letters 20, no. 8 (April 4, 2018): 2172–75. http://dx.doi.org/10.1021/acs.orglett.8b00449.

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33

Midorikawa, Kaoru, Kazutaka Hirakawa, and Shosuke Kawanishi. "Hydroxylation of Deoxyguanosine at 5′ Site of GG and GGG Sequences in Double-stranded DNA Induced by Carbamoyl Radicals." Free Radical Research 36, no. 6 (January 2002): 667–75. http://dx.doi.org/10.1080/10715760290029119.

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34

QUIRANTE, J., C. ESCOLANO, L. COSTEJA, and J. BONJOCH. "ChemInform Abstract: Cyclization of 1-(Carbamoyl)dichloromethyl Radicals Upon Activated Alkenes. A New Entry to 2-Azabicyclo(3.3.1)nonanes." ChemInform 28, no. 52 (August 2, 2010): no. http://dx.doi.org/10.1002/chin.199752176.

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35

Gill, G. Bryon, Gerald Pattenden, and Stephen J. Reynolds. "Cobalt-mediated reactions: inter- and intra-molecular additions of carbamoyl radicals to alkenes in the synthesis of amides and lactams." Journal of the Chemical Society, Perkin Transactions 1, no. 4 (1994): 369. http://dx.doi.org/10.1039/p19940000369.

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36

Camarillo-López, Raúl Horacio, Maricarmen Hernández Rodríguez, Mónica Adriana Torres-Ramos, Ivonne Maciel Arciniega-Martínez, Iohanan Daniel García-Marín, José Correa Basurto, Juan Vicente Méndez Méndez, and Martha Cecilia Rosales-Hernández. "Tert-butyl-(4-hydroxy-3-((3-(2-methylpiperidin-yl)propyl)carbamoyl)phenyl)carbamate Has Moderated Protective Activity in Astrocytes Stimulated with Amyloid Beta 1-42 and in a Scopolamine Model." Molecules 25, no. 21 (October 29, 2020): 5009. http://dx.doi.org/10.3390/molecules25215009.

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Alzheimer’s disease (AD) is a neurodegenerative disease with no cure nowadays; there is no treatment either to prevent or to stop its progression. In vitro studies suggested that tert-butyl-(4-hydroxy-3-((3-(2-methylpiperidin-yl)propyl)carbamoyl)phenyl) carbamate named the M4 compound can act as both β-secretase and an acetylcholinesterase inhibitor, preventing the amyloid beta peptide (Aβ) aggregation and the formation of fibrils (fAβ) from Aβ1-42. This work first aimed to assess in in vitro studies to see whether the death of astrocyte cells promoted by Aβ1-42 could be prevented. Second, our work investigated the ability of the M4 compound to inhibit amyloidogenesis using an in vivo model after scopolamine administration. The results showed that M4 possesses a moderate protective effect in astrocytes against Aβ1-42 due to a reduction in the TNF-α and free radicals observed in cell cultures. In the in vivo studies, however, no significant effect of M4 was observed in comparison with a galantamine model employed in rats, in which case this outcome was attributed to the bioavailability of M4 in the brain of the rats.

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37

Vlad, Ilinca Margareta, Diana Camelia Nuță, Robert Viorel Ancuceanu, Teodora Costea, Maria Coanda, Marcela Popa, Luminita Gabriela Marutescu, et al. "Insights into the Microbicidal, Antibiofilm, Antioxidant and Toxicity Profile of New O-Aryl-Carbamoyl-Oxymino-Fluorene Derivatives." International Journal of Molecular Sciences 24, no. 8 (April 10, 2023): 7020. http://dx.doi.org/10.3390/ijms24087020.

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The unprecedented increase in microbial resistance rates to all current drugs raises an acute need for the design of more effective antimicrobial strategies. Moreover, the importance of oxidative stress due to chronic inflammation in infections with resistant bacteria represents a key factor for the development of new antibacterial agents with potential antioxidant effects. Thus, the purpose of this study was to bioevaluate new O-aryl-carbamoyl-oxymino-fluorene derivatives for their potential use against infectious diseases. With this aim, their antimicrobial effect was evaluated using quantitative assays (minimum inhibitory/bactericidal/biofilms inhibitory concentrations) (MIC/MBC/MBIC), the obtained values being 0.156–10/0.312–10/0.009–1.25 mg/mL), while some of the involved mechanisms (i.e., membrane depolarization) were investigated by flow cytometry. The antioxidant activity was evaluated by studying the scavenger capacity of DPPH and ABTS•+ radicals and the toxicity was tested in vitro on three cell lines and in vivo on the crustacean Artemia franciscana Kellog. The four compounds derived from 9H-fluoren-9-one oxime proved to exhibit promising antimicrobial features and particularly, a significant antibiofilm activity. The presence of chlorine induced an electron-withdrawing effect, favoring the anti-Staphylococcus aureus and that of the methyl group exhibited a +I effect of enhancing the anti-Candida albicans activity. The IC50 values calculated in the two toxicity assays revealed similar values and the potential of these compounds to inhibit the proliferation of tumoral cells. Taken together, all these data demonstrate the potential of the tested compounds to be further used for the development of novel antimicrobial and anticancer agents.

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38

GILL, G. B., G. PATTENDEN, and S. J. REYNOLDS. "ChemInform Abstract: Cobalt-Mediated Reactions: Inter- and Intramolecular Additions of Carbamoyl Radicals to Alkenes in the Synthesis of Amides and Lactams." ChemInform 25, no. 24 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199424092.

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39

Jackson, Leon V., and John C. Walton. "Generation of aminoacyl radicals from 1-carbamoyl-1-methylcyclohexa-2,5- dienes: a new tin-free homolytic route to β- and γ-lactams." Chemical Communications, no. 23 (2000): 2327–28. http://dx.doi.org/10.1039/b007454n.

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40

Komatsu, Makiko, and Midori Hiramatsu. "Change of nitroxide radicals in the live rat head of senescence accelerated mice (SAM-P/8) after intraperitoneal injection of carbamoyl-proxyl." Neuroscience Research Supplements 19 (January 1994): S170. http://dx.doi.org/10.1016/0921-8696(94)92745-6.

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41

Zincircioğlu, S. Burhanedtin, Naime Canoruç, Şemsettin Osmanoğlu, M. Halim Başkan, I. Yeşim Dicle, and Murat Aydın. "Electron Paramagnetic Resonance of Some γ-Irradiated Amino Acid Derivatives." Zeitschrift für Naturforschung A 61, no. 10-11 (November 1, 2006): 577–82. http://dx.doi.org/10.1515/zna-2006-10-1110.

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γ -Irradiated powders of N-acetyl-L-arginine, Nα -carbamyl-L-arginine, N-glycyl-L-leucine and glycyl-L-alanine were investigated at room temperature by electron paramagnetic resonance. The observed species in N-acetyl-L-arginine and Nα -carbamyl-L-arginine were attributed to the CH2CHNHCNHNH2 radical, and those in N-glycyl-L-leucine and glycyl-L-alanine powders to (CH3)2CCH2 and CH3CHCOOH radicals.

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42

Jackson, Leon V., and John C. Walton. "ChemInform Abstract: Generation of Aminoacyl Radicals from 1-Carbamoyl-1-methylcyclohexa-2,5-dienes: A New Tin-Free Homolytic Route to β- and γ-Lactams." ChemInform 32, no. 14 (April 3, 2001): no. http://dx.doi.org/10.1002/chin.200114050.

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43

Franco Bella, A., Leon V. Jackson, and John C. Walton. "A kinetic EPR study of the dissociation of 1-carbamoyl-1-methylcyclohexa-2,5-dienyl radicals: release of aminoacyl radicals and their cyclisationElectronic supplementary information (ESI) available: Selected EPR spectra, measured radical concentrations and the corresponding rate constants at each temperature for each cyclohexadienyl. AM1 computed heats of formation and selected geometric parameters for a series of cyclohexadienyl radicals and dissociation products. UB3LYP computed energies for model aminoacyl radicals. See http://www.rsc.org/suppdata/p2/b2/b206768d/." Journal of the Chemical Society, Perkin Transactions 2, no. 11 (October 8, 2002): 1839–43. http://dx.doi.org/10.1039/b206768d.

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44

Tang, Jia-Jun, Meng-Yang Zhao, Ying-Jun Lin, Li-Hua Yang, and Long-Yong Xie. "Persulfate-Promoted Carbamoylation/Cyclization of Alkenes: Synthesis of Amide-Containing Quinazolinones." Molecules 29, no. 5 (February 25, 2024): 997. http://dx.doi.org/10.3390/molecules29050997.

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The incorporation of amide groups into biologically active molecules has been proven to be an efficient strategy for drug design and discovery. In this study, we present a simple and practical method for the synthesis of amide-containing quinazolin-4(3H)-ones under transition-metal-free conditions. This is achieved through a carbamoyl-radical-triggered cascade cyclization of N3-alkenyl-tethered quinazolinones. Notably, the carbamoyl radical is generated in situ from the oxidative decarboxylative process of oxamic acids in the presence of (NH4)2S2O8.

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45

Grossi, Loris. "N-alkyl and N-aryl-carbamoly radicals: a new σ-type radical." J. Chem. Soc., Chem. Commun., no. 17 (1989): 1248–50. http://dx.doi.org/10.1039/c39890001248.

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46

Petersen, Wade F., Richard J. K. Taylor, and James R. Donald. "Photoredox-catalyzed procedure for carbamoyl radical generation: 3,4-dihydroquinolin-2-one and quinolin-2-one synthesis." Organic & Biomolecular Chemistry 15, no. 27 (2017): 5831–45. http://dx.doi.org/10.1039/c7ob01274h.

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47

Osmanoğlu, Şemsettin, and M. Halim Başkan. "Electron Paramagnetic Resonance of Gamma Irradiation Damage Centres in Acetyl and Carbamyl-β-Methyl Choline Chloride." Journal of Chemical Research 2003, no. 1 (January 2003): 26–27. http://dx.doi.org/10.3184/030823403103172814.

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Abstract:

The EPR spectra of 7-irradiated powders of acetyl-β-methyl choline chloride (AβMCCl) and carbamyl-β-methyl choline chloride (CβMCCl) indicated the existence of the [Me3NĊMeCH2OCOMe]Cl radical in the former and of the [Me3NĊMeCH2OCONH2]Cl radical in the latter.

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48

Millán-Ortiz, Alejandra, German López-Valdez, Fernando Cortez-Guzmán, and Luis D. Miranda. "A novel carbamoyl radical based dearomatizing spiroacylation process." Chemical Communications 51, no. 39 (2015): 8345–48. http://dx.doi.org/10.1039/c4cc06192f.

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49

Jatoi, Ashique Hussain, Govind Goroba Pawar, Frédéric Robert, and Yannick Landais. "Visible-light mediated carbamoyl radical addition to heteroarenes." Chemical Communications 55, no. 4 (2019): 466–69. http://dx.doi.org/10.1039/c8cc08326f.

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50

Wei, Rongbiao, Liang Ge, Hongli Bao, Saihu Liao, and Yajun Li. "Copper-Catalyzed Nitrogenation of Aromatic and Aliphatic Aldehydes: A Direct Route to Carbamoyl Azides." Synthesis 51, no. 24 (September 23, 2019): 4645–49. http://dx.doi.org/10.1055/s-0039-1690683.

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Abstract:

An efficient copper-catalyzed synthesis of carbamoyl azides directly from aldehydes has been developed. Both aromatic aldehydes and aliphatic aldehydes, together with other commercially available reactants, can be used as substrates in this radical relay reaction. Broad substrate scope, simple operation, readily available reagents, and good functionality tolerance make this method very attractive.

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