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Copper-Mediated Domino Cyclization/Trifluoromethylation of Propargylic N-Hydroxylamines: Synthesis of 4-Trifluoromethyl-4-isoxazolines.

The Journal of organic chemistry

Wang Q, Tsui GC.
PMID: 29402075
J Org Chem. 2018 Mar 02;83(5):2971-2979. doi: 10.1021/acs.joc.7b03191. Epub 2018 Feb 09.

A Cu(OTf)

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Wang Q, Tsui GC. Copper-Mediated Domino Cyclization/Trifluoromethylation of Propargylic N-Hydroxylamines: Synthesis of 4-Trifluoromethyl-4-isoxazolines. J Org Chem. 2018;83(5):2971-2979doi: 10.1021/acs.joc.7b03191.
Wang, Q., & Tsui, G. C. (2018). Copper-Mediated Domino Cyclization/Trifluoromethylation of Propargylic N-Hydroxylamines: Synthesis of 4-Trifluoromethyl-4-isoxazolines. The Journal of organic chemistry, 83(5), 2971-2979. https://doi.org/10.1021/acs.joc.7b03191
Wang, Quande, and Tsui, Gavin Chit. "Copper-Mediated Domino Cyclization/Trifluoromethylation of Propargylic N-Hydroxylamines: Synthesis of 4-Trifluoromethyl-4-isoxazolines." The Journal of organic chemistry vol. 83,5 (2018): 2971-2979. doi: https://doi.org/10.1021/acs.joc.7b03191
Wang Q, Tsui GC. Copper-Mediated Domino Cyclization/Trifluoromethylation of Propargylic N-Hydroxylamines: Synthesis of 4-Trifluoromethyl-4-isoxazolines. J Org Chem. 2018 Mar 02;83(5):2971-2979. doi: 10.1021/acs.joc.7b03191. Epub 2018 Feb 09. PMID: 29402075.
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Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals.

The Analyst

Besson E, Gastaldi S, Bloch E, Zielonka J, Zielonka M, Kalyanaraman B, Aslan S, Karoui H, Rockenbauer A, Ouari O, Hardy M.
PMID: 31180410
Analyst. 2019 Jul 21;144(14):4194-4203. doi: 10.1039/c9an00468h. Epub 2019 Jun 10.

The generation of superoxide radical anion in biological systems is one of the major initiating events in the redox biology of NADPH oxidases and mitochondrial redox signalling. However, the pallette of chemical tools for superoxide detection is very limited,...

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Besson E, Gastaldi S, Bloch E, et al. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals. Analyst. 2019;144(14):4194-4203doi: 10.1039/c9an00468h.
Besson, E., Gastaldi, S., Bloch, E., Zielonka, J., Zielonka, M., Kalyanaraman, B., Aslan, S., Karoui, H., Rockenbauer, A., Ouari, O., & Hardy, M. (2019). Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals. The Analyst, 144(14), 4194-4203. https://doi.org/10.1039/c9an00468h
Besson, Eric, et al. "Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals." The Analyst vol. 144,14 (2019): 4194-4203. doi: https://doi.org/10.1039/c9an00468h
Besson E, Gastaldi S, Bloch E, Zielonka J, Zielonka M, Kalyanaraman B, Aslan S, Karoui H, Rockenbauer A, Ouari O, Hardy M. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals. Analyst. 2019 Jul 21;144(14):4194-4203. doi: 10.1039/c9an00468h. Epub 2019 Jun 10. PMID: 31180410.
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Broadening the reaction scope of unprotected aldoses via their corresponding nitrones: 1,3-dipolar cycloadditions with alkenes.

Organic & biomolecular chemistry

Messire G, Massicot F, Pascual L, Riguet E, Vasse JL, Behr JB.
PMID: 32666987
Org Biomol Chem. 2020 Jul 29;18(29):5708-5725. doi: 10.1039/d0ob01350a.

Condensation reactions of unprotected tetroses and pentoses with hydroxylamines afforded nitrones, which were easily converted to densely functionalized isoxazolidines in the presence of electron-poor alkenes. The 1,3-dipolar cycloaddition occurred with good facial discrimination of the chiral nitrone but under...

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Messire G, Massicot F, Pascual L, et al. Broadening the reaction scope of unprotected aldoses via their corresponding nitrones: 1,3-dipolar cycloadditions with alkenes. Org Biomol Chem. 2020;18(29):5708-5725doi: 10.1039/d0ob01350a.
Messire, G., Massicot, F., Pascual, L., Riguet, E., Vasse, J. L., & Behr, J. B. (2020). Broadening the reaction scope of unprotected aldoses via their corresponding nitrones: 1,3-dipolar cycloadditions with alkenes. Organic & biomolecular chemistry, 18(29), 5708-5725. https://doi.org/10.1039/d0ob01350a
Messire, Gatien, et al. "Broadening the reaction scope of unprotected aldoses via their corresponding nitrones: 1,3-dipolar cycloadditions with alkenes." Organic & biomolecular chemistry vol. 18,29 (2020): 5708-5725. doi: https://doi.org/10.1039/d0ob01350a
Messire G, Massicot F, Pascual L, Riguet E, Vasse JL, Behr JB. Broadening the reaction scope of unprotected aldoses via their corresponding nitrones: 1,3-dipolar cycloadditions with alkenes. Org Biomol Chem. 2020 Jul 29;18(29):5708-5725. doi: 10.1039/d0ob01350a. PMID: 32666987.
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O-Protected NH-free hydroxylamines: emerging electrophilic aminating reagents for organic synthesis.

Chemical communications (Cambridge, England)

Jinan D, Mondal PP, Nair AV, Sahoo B.
PMID: 34842254
Chem Commun (Camb). 2021 Dec 14;57(99):13495-13505. doi: 10.1039/d1cc05282a.

In this highlight, O-protected NH-free hydroxylamine derivatives have been evaluated in the construction of nitrogen-enriched compounds, such as primary amines, amides, and N-heterocycles, with high regio-, chemo- and stereoselectivity in the unprotected form, showcasing the late-stage functionalization of natural...

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Jinan D, Mondal PP, Nair AV, et al. O-Protected NH-free hydroxylamines: emerging electrophilic aminating reagents for organic synthesis. Chem Commun (Camb). 2021;57(99):13495-13505doi: 10.1039/d1cc05282a.
Jinan, D., Mondal, P. P., Nair, A. V., & Sahoo, B. (2021). O-Protected NH-free hydroxylamines: emerging electrophilic aminating reagents for organic synthesis. Chemical communications (Cambridge, England), 57(99), 13495-13505. https://doi.org/10.1039/d1cc05282a
Jinan, Dilsha, et al. "O-Protected NH-free hydroxylamines: emerging electrophilic aminating reagents for organic synthesis." Chemical communications (Cambridge, England) vol. 57,99 (2021): 13495-13505. doi: https://doi.org/10.1039/d1cc05282a
Jinan D, Mondal PP, Nair AV, Sahoo B. O-Protected NH-free hydroxylamines: emerging electrophilic aminating reagents for organic synthesis. Chem Commun (Camb). 2021 Dec 14;57(99):13495-13505. doi: 10.1039/d1cc05282a. PMID: 34842254.
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Hydroxylamine-mediated C-C amination via an aza-hock rearrangement.

Nature communications

Wang T, Stein PM, Shi H, Hu C, Rudolph M, Hashmi ASK.
PMID: 34857758
Nat Commun. 2021 Dec 02;12(1):7029. doi: 10.1038/s41467-021-27271-y.

Despite the widespread use of anilines, synthetic challenges to these targets still exist. Selectivity is often an issue, when using the traditional nitration-reduction sequence or more modern approaches, including arene C-H aminations catalyzed by transition metals, photosensitizers, or electrodes....

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Wang T, Stein PM, Shi H, et al. Hydroxylamine-mediated C-C amination via an aza-hock rearrangement. Nat Commun. 2021;12(1):7029doi: 10.1038/s41467-021-27271-y.
Wang, T., Stein, P. M., Shi, H., Hu, C., Rudolph, M., & Hashmi, A. S. K. (2021). Hydroxylamine-mediated C-C amination via an aza-hock rearrangement. Nature communications, 12(1), 7029. https://doi.org/10.1038/s41467-021-27271-y
Wang, Tao, et al. "Hydroxylamine-mediated C-C amination via an aza-hock rearrangement." Nature communications vol. 12,1 (2021): 7029. doi: https://doi.org/10.1038/s41467-021-27271-y
Wang T, Stein PM, Shi H, Hu C, Rudolph M, Hashmi ASK. Hydroxylamine-mediated C-C amination via an aza-hock rearrangement. Nat Commun. 2021 Dec 02;12(1):7029. doi: 10.1038/s41467-021-27271-y. PMID: 34857758; PMCID: PMC8640056.
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Chemoselective Amide-Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions.

Angewandte Chemie (International ed. in English)

Deng X, Zhou G, Tian J, Srinivasan R.
PMID: 33135292
Angew Chem Int Ed Engl. 2021 Mar 22;60(13):7024-7029. doi: 10.1002/anie.202012459. Epub 2020 Dec 28.

We report the facile amide-forming ligation of acylsilanes with hydroxylamines (ASHA ligation) under aqueous conditions. The ligation is fast, chemoselective, mild, high-yielding and displays excellent functional-group tolerance. Late-stage modifications of an array of marketed drugs, peptides, natural products, and...

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Deng X, Zhou G, Tian J, et al. Chemoselective Amide-Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions. Angew Chem Int Ed Engl. 2020;60(13):7024-7029doi: 10.1002/anie.202012459.
Deng, X., Zhou, G., Tian, J., & Srinivasan, R. (2021). Chemoselective Amide-Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions. Angewandte Chemie (International ed. in English), 60(13), 7024-7029. https://doi.org/10.1002/anie.202012459
Deng, Xingwang, et al. "Chemoselective Amide-Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions." Angewandte Chemie (International ed. in English) vol. 60,13 (2021): 7024-7029. doi: https://doi.org/10.1002/anie.202012459
Deng X, Zhou G, Tian J, Srinivasan R. Chemoselective Amide-Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions. Angew Chem Int Ed Engl. 2021 Mar 22;60(13):7024-7029. doi: 10.1002/anie.202012459. Epub 2020 Dec 28. PMID: 33135292.
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O-Protected NH-free hydroxylamines: emerging electrophilic aminating reagents for organic synthesis.

Chemical communications (Cambridge, England)

Jinan D, Mondal PP, Nair AV, Sahoo B.
PMID: 34842254
Chem Commun (Camb). 2021 Dec 14;57(99):13495-13505. doi: 10.1039/d1cc05282a.

In this highlight, O-protected NH-free hydroxylamine derivatives have been evaluated in the construction of nitrogen-enriched compounds, such as primary amines, amides, and N-heterocycles, with high regio-, chemo- and stereoselectivity in the unprotected form, showcasing the late-stage functionalization of natural...

Cite
Jinan D, Mondal PP, Nair AV, et al. O-Protected NH-free hydroxylamines: emerging electrophilic aminating reagents for organic synthesis. Chem Commun (Camb). 2021;57(99):13495-13505doi: 10.1039/d1cc05282a.
Jinan, D., Mondal, P. P., Nair, A. V., & Sahoo, B. (2021). O-Protected NH-free hydroxylamines: emerging electrophilic aminating reagents for organic synthesis. Chemical communications (Cambridge, England), 57(99), 13495-13505. https://doi.org/10.1039/d1cc05282a
Jinan, Dilsha, et al. "O-Protected NH-free hydroxylamines: emerging electrophilic aminating reagents for organic synthesis." Chemical communications (Cambridge, England) vol. 57,99 (2021): 13495-13505. doi: https://doi.org/10.1039/d1cc05282a
Jinan D, Mondal PP, Nair AV, Sahoo B. O-Protected NH-free hydroxylamines: emerging electrophilic aminating reagents for organic synthesis. Chem Commun (Camb). 2021 Dec 14;57(99):13495-13505. doi: 10.1039/d1cc05282a. PMID: 34842254.
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Visible-Light Promoted Distereodivergent Intramolecular Oxyamidation of Alkenes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Ren X, Guo Q, Chen J, Xie H, Xu Q, Lu Z.
PMID: 27770547
Chemistry. 2016 Dec 23;22(52):18695-18699. doi: 10.1002/chem.201603977. Epub 2016 Nov 15.

The visible-light-promoted diastereodivergent intramolecular oxyamination of alkenes is described to construct oxazolindinones, pyrrolidinones and imidazolidones via mild generation of primary amidyl radicals from functionalized hydroxylamines. A unique phenomenon of highly diastereoselective ring-opening of aziridines controlled by electron sacrifices was...

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Ren X, Guo Q, Chen J, et al. Visible-Light Promoted Distereodivergent Intramolecular Oxyamidation of Alkenes. Chemistry. 2016;22(52):18695-18699doi: 10.1002/chem.201603977.
Ren, X., Guo, Q., Chen, J., Xie, H., Xu, Q., & Lu, Z. (2016). Visible-Light Promoted Distereodivergent Intramolecular Oxyamidation of Alkenes. Chemistry (Weinheim an der Bergstrasse, Germany), 22(52), 18695-18699. https://doi.org/10.1002/chem.201603977
Ren, Xiang, et al. "Visible-Light Promoted Distereodivergent Intramolecular Oxyamidation of Alkenes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,52 (2016): 18695-18699. doi: https://doi.org/10.1002/chem.201603977
Ren X, Guo Q, Chen J, Xie H, Xu Q, Lu Z. Visible-Light Promoted Distereodivergent Intramolecular Oxyamidation of Alkenes. Chemistry. 2016 Dec 23;22(52):18695-18699. doi: 10.1002/chem.201603977. Epub 2016 Nov 15. PMID: 27770547.
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Homoallyllic nitrone isomerization: convenient enantioselective synthesis of homoallylic nitrones and homoallylic hydroxylamines.

Organic letters

Cheng HS, Seow AH, Loh TP.
PMID: 18537248
Org Lett. 2008 Jul 03;10(13):2805-7. doi: 10.1021/ol800925v. Epub 2008 Jun 07.

An alpha-regioselective synthesis of homoallylic nitrones from aldehydes is reported on the basis of [3,3]-sigmatropic rearrangement. The products are obtained in up to 99% enantioselectivity and up to 80% yield under environmentally benign and mild reaction conditions.

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Cheng HS, Seow AH, Loh TP. Homoallyllic nitrone isomerization: convenient enantioselective synthesis of homoallylic nitrones and homoallylic hydroxylamines. Org Lett. 2008;10(13):2805-7doi: 10.1021/ol800925v.
Cheng, H. S., Seow, A. H., & Loh, T. P. (2008). Homoallyllic nitrone isomerization: convenient enantioselective synthesis of homoallylic nitrones and homoallylic hydroxylamines. Organic letters, 10(13), 2805-7. https://doi.org/10.1021/ol800925v
Cheng, Hin-Soon, et al. "Homoallyllic nitrone isomerization: convenient enantioselective synthesis of homoallylic nitrones and homoallylic hydroxylamines." Organic letters vol. 10,13 (2008): 2805-7. doi: https://doi.org/10.1021/ol800925v
Cheng HS, Seow AH, Loh TP. Homoallyllic nitrone isomerization: convenient enantioselective synthesis of homoallylic nitrones and homoallylic hydroxylamines. Org Lett. 2008 Jul 03;10(13):2805-7. doi: 10.1021/ol800925v. Epub 2008 Jun 07. PMID: 18537248.
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Dialkylzinc-assisted alkynylation of nitrones.

Organic letters

Pinet S, Pandya SU, Chavant PY, Ayling A, Vallee Y.
PMID: 11975604
Org Lett. 2002 May 02;4(9):1463-6. doi: 10.1021/ol025618n.

[reaction: see text]. Reaction of nitrones with terminal alkynes takes place readily in the presence of a substoichiometric amount of diethylzinc in toluene, affording N-propargyl-hydroxylamines in excellent yields and purity.

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Pinet S, Pandya SU, Chavant PY, et al. Dialkylzinc-assisted alkynylation of nitrones. Org Lett. 2002;4(9):1463-6doi: 10.1021/ol025618n.
Pinet, S., Pandya, S. U., Chavant, P. Y., Ayling, A., & Vallee, Y. (2002). Dialkylzinc-assisted alkynylation of nitrones. Organic letters, 4(9), 1463-6. https://doi.org/10.1021/ol025618n
Pinet, Sandra, et al. "Dialkylzinc-assisted alkynylation of nitrones." Organic letters vol. 4,9 (2002): 1463-6. doi: https://doi.org/10.1021/ol025618n
Pinet S, Pandya SU, Chavant PY, Ayling A, Vallee Y. Dialkylzinc-assisted alkynylation of nitrones. Org Lett. 2002 May 02;4(9):1463-6. doi: 10.1021/ol025618n. PMID: 11975604.
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Fluorescent, Siderophore-Based Chelators. Design and Synthesis of a Trispyrenyl Trishydroxamate Ligand, an Intramolecular Excimer-Forming Sensing Molecule Which Responds to Iron(III) and Gallium(III) Metal Cations.

The Journal of organic chemistry

Fages F, Bodenant B, Weil T.
PMID: 11667267
J Org Chem. 1996 Jun 14;61(12):3956-3961. doi: 10.1021/jo960191h.

Two pyrene-labeled hydroxylamines, 5-Bn and 5-Bz, O-protected with the benzyl and the benzoyl group, respectively, have been prepared for the generation of siderophore-based new chelators incorporating both the pyrene chromophore and the hydroxamic acid functionality. 5-Bz formed the starting...

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Fages F, Bodenant B, Weil T. Fluorescent, Siderophore-Based Chelators. Design and Synthesis of a Trispyrenyl Trishydroxamate Ligand, an Intramolecular Excimer-Forming Sensing Molecule Which Responds to Iron(III) and Gallium(III) Metal Cations. J Org Chem. 1996;61(12):3956-3961doi: 10.1021/jo960191h.
Fages, F., Bodenant, B., & Weil, T. (1996). Fluorescent, Siderophore-Based Chelators. Design and Synthesis of a Trispyrenyl Trishydroxamate Ligand, an Intramolecular Excimer-Forming Sensing Molecule Which Responds to Iron(III) and Gallium(III) Metal Cations. The Journal of organic chemistry, 61(12), 3956-3961. https://doi.org/10.1021/jo960191h
Fages, Frédéric, et al. "Fluorescent, Siderophore-Based Chelators. Design and Synthesis of a Trispyrenyl Trishydroxamate Ligand, an Intramolecular Excimer-Forming Sensing Molecule Which Responds to Iron(III) and Gallium(III) Metal Cations." The Journal of organic chemistry vol. 61,12 (1996): 3956-3961. doi: https://doi.org/10.1021/jo960191h
Fages F, Bodenant B, Weil T. Fluorescent, Siderophore-Based Chelators. Design and Synthesis of a Trispyrenyl Trishydroxamate Ligand, an Intramolecular Excimer-Forming Sensing Molecule Which Responds to Iron(III) and Gallium(III) Metal Cations. J Org Chem. 1996 Jun 14;61(12):3956-3961. doi: 10.1021/jo960191h. PMID: 11667267.
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Indium-mediated reduction of hydroxylamines to amines.

Organic letters

Cicchi S, Bonanni M, Cardona F, Revuelta J, Goti A.
PMID: 12735774
Org Lett. 2003 May 15;5(10):1773-6. doi: 10.1021/ol034434l.

[reaction: see text] A novel and simple procedure for reduction of hydroxylamines to the corresponding amines by means of indium powder in aqueous media is reported. Applicability to one-pot reactions and isoxazolidine N-O bond reduction is also demonstrated. A...

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Cicchi S, Bonanni M, Cardona F, et al. Indium-mediated reduction of hydroxylamines to amines. Org Lett. 2003;5(10):1773-6doi: 10.1021/ol034434l.
Cicchi, S., Bonanni, M., Cardona, F., Revuelta, J., & Goti, A. (2003). Indium-mediated reduction of hydroxylamines to amines. Organic letters, 5(10), 1773-6. https://doi.org/10.1021/ol034434l
Cicchi, Stefano, et al. "Indium-mediated reduction of hydroxylamines to amines." Organic letters vol. 5,10 (2003): 1773-6. doi: https://doi.org/10.1021/ol034434l
Cicchi S, Bonanni M, Cardona F, Revuelta J, Goti A. Indium-mediated reduction of hydroxylamines to amines. Org Lett. 2003 May 15;5(10):1773-6. doi: 10.1021/ol034434l. PMID: 12735774.
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Showing 25 to 36 of 176 entries