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Showing 13 to 24 of 56 entries
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Novel chalcone-based fluorescent human histamine h(3) receptor ligands as pharmacological tools.

Frontiers in systems neuroscience

Tomasch M, Schwed JS, Weizel L, Stark H.
PMID: 22470321
Front Syst Neurosci. 2012 Mar 26;6:14. doi: 10.3389/fnsys.2012.00014. eCollection 2012.

Novel fluorescent chalcone-based ligands at human histamine H(3) receptors (hH(3)R) have been designed, synthesized, and characterized. Compounds described are non-imidazole analogs of ciproxifan with a tetralone motif. Tetralones as chemical precursors and related fluorescent chalcones exhibit affinities at hH(3)R...

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Tomasch M, Schwed JS, Weizel L, et al. Novel chalcone-based fluorescent human histamine h(3) receptor ligands as pharmacological tools. Front Syst Neurosci. 2012;6:14doi: 10.3389/fnsys.2012.00014.
Tomasch, M., Schwed, J. S., Weizel, L., & Stark, H. (2012). Novel chalcone-based fluorescent human histamine h(3) receptor ligands as pharmacological tools. Frontiers in systems neuroscience, 614. https://doi.org/10.3389/fnsys.2012.00014
Tomasch, Miriam, et al. "Novel chalcone-based fluorescent human histamine h(3) receptor ligands as pharmacological tools." Frontiers in systems neuroscience vol. 6 (2012): 14. doi: https://doi.org/10.3389/fnsys.2012.00014
Tomasch M, Schwed JS, Weizel L, Stark H. Novel chalcone-based fluorescent human histamine h(3) receptor ligands as pharmacological tools. Front Syst Neurosci. 2012 Mar 26;6:14. doi: 10.3389/fnsys.2012.00014. eCollection 2012. PMID: 22470321; PMCID: PMC3312100.
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3-(Hetero)aryl-4-indolylamino-α-tetralones by diastereoselective internal redox cyclization: an "azaenamine" conjugate addition.

The Journal of organic chemistry

Ghavtadze N, Narayan R, Wibbeling B, Würthwein EU.
PMID: 21657793
J Org Chem. 2011 Jul 01;76(13):5185-97. doi: 10.1021/jo200896y. Epub 2011 Jun 10.

(E)-3-(hetero)aryl-1-(2-((E)-(indolin-1-ylimino)methyl)phenyl)prop-2-en-1-ones 1 undergo 6-exo-trig cyclization reactions upon treatment with BF(3)·Me(2)S in dichloromethane at low temperature to give the tetralones 10 in good yield. This cyclization process can be considered to be an intramolecular Michael-type addition which is accompanied by...

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Ghavtadze N, Narayan R, Wibbeling B, et al. 3-(Hetero)aryl-4-indolylamino-α-tetralones by diastereoselective internal redox cyclization: an "azaenamine" conjugate addition. J Org Chem. 2011;76(13):5185-97doi: 10.1021/jo200896y.
Ghavtadze, N., Narayan, R., Wibbeling, B., & Würthwein, E. U. (2011). 3-(Hetero)aryl-4-indolylamino-α-tetralones by diastereoselective internal redox cyclization: an "azaenamine" conjugate addition. The Journal of organic chemistry, 76(13), 5185-97. https://doi.org/10.1021/jo200896y
Ghavtadze, Nugzar, et al. "3-(Hetero)aryl-4-indolylamino-α-tetralones by diastereoselective internal redox cyclization: an "azaenamine" conjugate addition." The Journal of organic chemistry vol. 76,13 (2011): 5185-97. doi: https://doi.org/10.1021/jo200896y
Ghavtadze N, Narayan R, Wibbeling B, Würthwein EU. 3-(Hetero)aryl-4-indolylamino-α-tetralones by diastereoselective internal redox cyclization: an "azaenamine" conjugate addition. J Org Chem. 2011 Jul 01;76(13):5185-97. doi: 10.1021/jo200896y. Epub 2011 Jun 10. PMID: 21657793.
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Thermal and metal-catalyzed cyclization of 1-substituted 3,5-dien-1-ynes via a [1,7]-hydrogen shift: development of a tandem aldol condensation-dehydration and aromatization catalysis between 3-en-1-yn-5-al units and cyclic ketones.

Journal of the American Chemical Society

Lian JJ, Lin CC, Chang HK, Chen PC, Liu RS.
PMID: 16866518
J Am Chem Soc. 2006 Aug 02;128(30):9661-7. doi: 10.1021/ja061203b.

This work investigates the feasibility of thermal and catalytic cyclization of 6,6-disubstituted 3,5-dien-1-ynes via a 1,7-hydrogen shift. Our strategy began with an understanding of a structural correlation of 3,5-dien-1-ynes with their thermal cyclization efficiency. Thermal cyclization proceeded only with...

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Lian JJ, Lin CC, Chang HK, et al. Thermal and metal-catalyzed cyclization of 1-substituted 3,5-dien-1-ynes via a [1,7]-hydrogen shift: development of a tandem aldol condensation-dehydration and aromatization catalysis between 3-en-1-yn-5-al units and cyclic ketones. J Am Chem Soc. 2006;128(30):9661-7doi: 10.1021/ja061203b.
Lian, J. J., Lin, C. C., Chang, H. K., Chen, P. C., & Liu, R. S. (2006). Thermal and metal-catalyzed cyclization of 1-substituted 3,5-dien-1-ynes via a [1,7]-hydrogen shift: development of a tandem aldol condensation-dehydration and aromatization catalysis between 3-en-1-yn-5-al units and cyclic ketones. Journal of the American Chemical Society, 128(30), 9661-7. https://doi.org/10.1021/ja061203b
Lian, Jian-Jou, et al. "Thermal and metal-catalyzed cyclization of 1-substituted 3,5-dien-1-ynes via a [1,7]-hydrogen shift: development of a tandem aldol condensation-dehydration and aromatization catalysis between 3-en-1-yn-5-al units and cyclic ketones." Journal of the American Chemical Society vol. 128,30 (2006): 9661-7. doi: https://doi.org/10.1021/ja061203b
Lian JJ, Lin CC, Chang HK, Chen PC, Liu RS. Thermal and metal-catalyzed cyclization of 1-substituted 3,5-dien-1-ynes via a [1,7]-hydrogen shift: development of a tandem aldol condensation-dehydration and aromatization catalysis between 3-en-1-yn-5-al units and cyclic ketones. J Am Chem Soc. 2006 Aug 02;128(30):9661-7. doi: 10.1021/ja061203b. PMID: 16866518.
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Tuning O2 Reactivity through Synergistic Photo/Copper Catalysis: Direct Synthesis of 4-Aryl tetralones via Cyclodimerization-Oxygenation of Styrenes.

Chemistry, an Asian journal

Zhang X, Yi H, Luo Y, Lei A.
PMID: 27319756
Chem Asian J. 2016 Aug 05;11(15):2117-20. doi: 10.1002/asia.201600758. Epub 2016 Jul 08.

A transformation is presented that enables chemists to construct 4-aryl tetralones via visible-light-induced cyclodimerization-oxygenation of styrene under very mild conditions. Adding a catalytic amount of CuOAc obviously improves the yield. A mechanistic study reveals that the photoredox catalyst played...

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Zhang X, Yi H, Luo Y, et al. Tuning O2 Reactivity through Synergistic Photo/Copper Catalysis: Direct Synthesis of 4-Aryl tetralones via Cyclodimerization-Oxygenation of Styrenes. Chem Asian J. 2016;11(15):2117-20doi: 10.1002/asia.201600758.
Zhang, X., Yi, H., Luo, Y., & Lei, A. (2016). Tuning O2 Reactivity through Synergistic Photo/Copper Catalysis: Direct Synthesis of 4-Aryl tetralones via Cyclodimerization-Oxygenation of Styrenes. Chemistry, an Asian journal, 11(15), 2117-20. https://doi.org/10.1002/asia.201600758
Zhang, Xu, et al. "Tuning O2 Reactivity through Synergistic Photo/Copper Catalysis: Direct Synthesis of 4-Aryl tetralones via Cyclodimerization-Oxygenation of Styrenes." Chemistry, an Asian journal vol. 11,15 (2016): 2117-20. doi: https://doi.org/10.1002/asia.201600758
Zhang X, Yi H, Luo Y, Lei A. Tuning O2 Reactivity through Synergistic Photo/Copper Catalysis: Direct Synthesis of 4-Aryl tetralones via Cyclodimerization-Oxygenation of Styrenes. Chem Asian J. 2016 Aug 05;11(15):2117-20. doi: 10.1002/asia.201600758. Epub 2016 Jul 08. PMID: 27319756.
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Facile synthesis of fused polycyclic compounds via intramolecular oxidative cyclization/aromatization of β-tetralone or β-tetralone oximes.

Organic & biomolecular chemistry

Jiang Y, Yu SW, Yang Y, Liu YL, Xu XY, Zhang XM, Yuan WC.
PMID: 30422145
Org Biomol Chem. 2018 Nov 28;16(46):9003-9010. doi: 10.1039/c8ob02031k.

A mild and efficient NBS promoted intramolecular oxidative cyclization/aromatization of β-tetralone oximes has been explored. Under the optimized conditions, fused α-carbolines containing pentacyclic rings were obtained in moderate to good yields. Furthermore, various benzo[5,6]chromeno[2,3-b]indoles were successfully synthesized in moderate...

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Jiang Y, Yu SW, Yang Y, et al. Facile synthesis of fused polycyclic compounds via intramolecular oxidative cyclization/aromatization of β-tetralone or β-tetralone oximes. Org Biomol Chem. 2018;16(46):9003-9010doi: 10.1039/c8ob02031k.
Jiang, Y., Yu, S. W., Yang, Y., Liu, Y. L., Xu, X. Y., Zhang, X. M., & Yuan, W. C. (2018). Facile synthesis of fused polycyclic compounds via intramolecular oxidative cyclization/aromatization of β-tetralone or β-tetralone oximes. Organic & biomolecular chemistry, 16(46), 9003-9010. https://doi.org/10.1039/c8ob02031k
Jiang, Yan, et al. "Facile synthesis of fused polycyclic compounds via intramolecular oxidative cyclization/aromatization of β-tetralone or β-tetralone oximes." Organic & biomolecular chemistry vol. 16,46 (2018): 9003-9010. doi: https://doi.org/10.1039/c8ob02031k
Jiang Y, Yu SW, Yang Y, Liu YL, Xu XY, Zhang XM, Yuan WC. Facile synthesis of fused polycyclic compounds via intramolecular oxidative cyclization/aromatization of β-tetralone or β-tetralone oximes. Org Biomol Chem. 2018 Nov 28;16(46):9003-9010. doi: 10.1039/c8ob02031k. PMID: 30422145.
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Asymmetric Synthesis of 1-Tetralones Bearing A Remote Quaternary Stereocenter through Rh-Catalyzed C-C Activation of Cyclopentanones.

Bulletin of the Chemical Society of Japan

Ochi S, Xia Y, Dong G.
PMID: 34675442
Bull Chem Soc Jpn. 2020;93(10):1213-1217. doi: 10.1246/bcsj.20200147. Epub 2020 Jun 05.

Herein, we describe the preparation of 1-tetralones bearing a remote quaternary stereocenter in a highly enantioselective manner. A sequence of Pd-catalyzed asymmetric 1,4-addition and Rh-catalyzed enantiospecific C-C/C-H activation delivers diverse 1-tetralones with a C4 quaternary stereocenter, which are prepared...

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Ochi S, Xia Y, Dong G. Asymmetric Synthesis of 1-Tetralones Bearing A Remote Quaternary Stereocenter through Rh-Catalyzed C-C Activation of Cyclopentanones. Bull Chem Soc Jpn. 2020;93(10):1213-1217doi: 10.1246/bcsj.20200147.
Ochi, S., Xia, Y., & Dong, G. (2020). Asymmetric Synthesis of 1-Tetralones Bearing A Remote Quaternary Stereocenter through Rh-Catalyzed C-C Activation of Cyclopentanones. Bulletin of the Chemical Society of Japan, 93(10), 1213-1217. https://doi.org/10.1246/bcsj.20200147
Ochi, Shusuke, et al. "Asymmetric Synthesis of 1-Tetralones Bearing A Remote Quaternary Stereocenter through Rh-Catalyzed C-C Activation of Cyclopentanones." Bulletin of the Chemical Society of Japan vol. 93,10 (2020): 1213-1217. doi: https://doi.org/10.1246/bcsj.20200147
Ochi S, Xia Y, Dong G. Asymmetric Synthesis of 1-Tetralones Bearing A Remote Quaternary Stereocenter through Rh-Catalyzed C-C Activation of Cyclopentanones. Bull Chem Soc Jpn. 2020;93(10):1213-1217. doi: 10.1246/bcsj.20200147. Epub 2020 Jun 05. PMID: 34675442; PMCID: PMC8528243.
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Visible-Light-Promoted Multistep Tandem Reaction of Vinyl Azides toward the Formation of 1-Tetralones.

The Journal of organic chemistry

Jiao MJ, Hu Q, Hu XQ, Xu PF.
PMID: 34794309
J Org Chem. 2021 Dec 03;86(23):17156-17163. doi: 10.1021/acs.joc.1c02261. Epub 2021 Nov 19.

A visible-light-driven multistep tandem reaction between vinyl azides and alkyl bromides has been developed leading to the formation of tetralone skeletons under mild conditions, which can be easily scaled up to the gram scale. Various 1-tetralone derivatives are synthesized...

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Jiao MJ, Hu Q, Hu XQ, et al. Visible-Light-Promoted Multistep Tandem Reaction of Vinyl Azides toward the Formation of 1-Tetralones. J Org Chem. 2021;86(23):17156-17163doi: 10.1021/acs.joc.1c02261.
Jiao, M. J., Hu, Q., Hu, X. Q., & Xu, P. F. (2021). Visible-Light-Promoted Multistep Tandem Reaction of Vinyl Azides toward the Formation of 1-Tetralones. The Journal of organic chemistry, 86(23), 17156-17163. https://doi.org/10.1021/acs.joc.1c02261
Jiao, Meng-Jie, et al. "Visible-Light-Promoted Multistep Tandem Reaction of Vinyl Azides toward the Formation of 1-Tetralones." The Journal of organic chemistry vol. 86,23 (2021): 17156-17163. doi: https://doi.org/10.1021/acs.joc.1c02261
Jiao MJ, Hu Q, Hu XQ, Xu PF. Visible-Light-Promoted Multistep Tandem Reaction of Vinyl Azides toward the Formation of 1-Tetralones. J Org Chem. 2021 Dec 03;86(23):17156-17163. doi: 10.1021/acs.joc.1c02261. Epub 2021 Nov 19. PMID: 34794309.
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Photoenolization as a convenient driver for the synthesis of plasmonic nanostructures.

Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology

Cely-Pinto M, Scaiano JC.
PMID: 34787843
Photochem Photobiol Sci. 2021 Dec;20(12):1611-1619. doi: 10.1007/s43630-021-00133-8. Epub 2021 Nov 17.

Substituted tetralones such as 3,3,6,8-tetramethyl-1-tetralone undergo photoenolization to produce a photoenol excited state with a lifetime around ~ 3 μs, which involves the carbonyl triplet state of the ketone (τ ~ 1.9 ns), as a precursor; the excited photoenol...

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Cely-Pinto M, Scaiano JC. Photoenolization as a convenient driver for the synthesis of plasmonic nanostructures. Photochem Photobiol Sci. 2021;20(12):1611-1619doi: 10.1007/s43630-021-00133-8.
Cely-Pinto, M., & Scaiano, J. C. (2021). Photoenolization as a convenient driver for the synthesis of plasmonic nanostructures. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 20(12), 1611-1619. https://doi.org/10.1007/s43630-021-00133-8
Cely-Pinto, Melissa, and Scaiano, Juan C. "Photoenolization as a convenient driver for the synthesis of plasmonic nanostructures." Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology vol. 20,12 (2021): 1611-1619. doi: https://doi.org/10.1007/s43630-021-00133-8
Cely-Pinto M, Scaiano JC. Photoenolization as a convenient driver for the synthesis of plasmonic nanostructures. Photochem Photobiol Sci. 2021 Dec;20(12):1611-1619. doi: 10.1007/s43630-021-00133-8. Epub 2021 Nov 17. PMID: 34787843.
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Asymmetric and nonasymmetric addition of RLi and RMgX to 3-methoxynaphthalen-2-yl oxazolines and imines. An approach to substituted 2-tetralones.

The Journal of organic chemistry

Kolotuchin SV, Meyers AI.
PMID: 10814192
J Org Chem. 2000 May 19;65(10):3018-26. doi: 10.1021/jo991727c.

Chiral and achiral 3-methoxynaphthalen-2-yl oxazolines 4a,b failed to undergo an aromatic nucleophilic displacement of the 3-methoxy group with organolithium reagents and instead afforded dihydronaphthalenes 9 and 14 in 30-95% yield. Dihydronaphthalenes 9 (racemic) and 14 (nonracemic) were easily converted...

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Kolotuchin SV, Meyers AI. Asymmetric and nonasymmetric addition of RLi and RMgX to 3-methoxynaphthalen-2-yl oxazolines and imines. An approach to substituted 2-tetralones. J Org Chem. 2000;65(10):3018-26doi: 10.1021/jo991727c.
Kolotuchin, S. V., & Meyers, A. I. (2000). Asymmetric and nonasymmetric addition of RLi and RMgX to 3-methoxynaphthalen-2-yl oxazolines and imines. An approach to substituted 2-tetralones. The Journal of organic chemistry, 65(10), 3018-26. https://doi.org/10.1021/jo991727c
Kolotuchin, and Meyers. "Asymmetric and nonasymmetric addition of RLi and RMgX to 3-methoxynaphthalen-2-yl oxazolines and imines. An approach to substituted 2-tetralones." The Journal of organic chemistry vol. 65,10 (2000): 3018-26. doi: https://doi.org/10.1021/jo991727c
Kolotuchin SV, Meyers AI. Asymmetric and nonasymmetric addition of RLi and RMgX to 3-methoxynaphthalen-2-yl oxazolines and imines. An approach to substituted 2-tetralones. J Org Chem. 2000 May 19;65(10):3018-26. doi: 10.1021/jo991727c. PMID: 10814192.
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Oxime derivatives as α-electrophiles. from α-tetralone oximes to tetracyclic frameworks.

Organic letters

Quiclet-Sire B, Tölle N, Zafar SN, Zard SZ.
PMID: 21615103
Org Lett. 2011 Jun 17;13(12):3266-9. doi: 10.1021/ol2012204. Epub 2011 May 26.

When subjected to the conditions of a Semmler-Wolff/Schroeter aromatization, the oximes of 4-benzyl-substituted tetralones undergo an electrophilic aromatic substitution reaction to form tetracyclic frameworks.

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Quiclet-Sire B, Tölle N, Zafar SN, et al. Oxime derivatives as α-electrophiles. from α-tetralone oximes to tetracyclic frameworks. Org Lett. 2011;13(12):3266-9doi: 10.1021/ol2012204.
Quiclet-Sire, B., Tölle, N., Zafar, S. N., & Zard, S. Z. (2011). Oxime derivatives as α-electrophiles. from α-tetralone oximes to tetracyclic frameworks. Organic letters, 13(12), 3266-9. https://doi.org/10.1021/ol2012204
Quiclet-Sire, Béatrice, et al. "Oxime derivatives as α-electrophiles. from α-tetralone oximes to tetracyclic frameworks." Organic letters vol. 13,12 (2011): 3266-9. doi: https://doi.org/10.1021/ol2012204
Quiclet-Sire B, Tölle N, Zafar SN, Zard SZ. Oxime derivatives as α-electrophiles. from α-tetralone oximes to tetracyclic frameworks. Org Lett. 2011 Jun 17;13(12):3266-9. doi: 10.1021/ol2012204. Epub 2011 May 26. PMID: 21615103.
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BINAP/1,4-diamine-ruthenium(II) complexes for efficient asymmetric hydrogenation of 1-tetralones and analogues.

Organic letters

Ohkuma T, Hattori T, Ooka H, Inoue T, Noyori R.
PMID: 15281743
Org Lett. 2004 Aug 05;6(16):2681-3. doi: 10.1021/ol049157c.

A combined system of a RuCl(2)(binap)(1,4-diamine) complex and t-C(4)H(9)OK in i-C(3)H(7)OH catalyzes enantioselective hydrogenation of various 1-tetralone derivatives and some methylated 2-cyclohexenones. Hydrogenation of 2-methyl-1-tetralone under dynamic kinetic resolution gives the cis alcohol with high ee. [reaction: see text]

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Ohkuma T, Hattori T, Ooka H, et al. BINAP/1,4-diamine-ruthenium(II) complexes for efficient asymmetric hydrogenation of 1-tetralones and analogues. Org Lett. 2004;6(16):2681-3doi: 10.1021/ol049157c.
Ohkuma, T., Hattori, T., Ooka, H., Inoue, T., & Noyori, R. (2004). BINAP/1,4-diamine-ruthenium(II) complexes for efficient asymmetric hydrogenation of 1-tetralones and analogues. Organic letters, 6(16), 2681-3. https://doi.org/10.1021/ol049157c
Ohkuma, Takeshi, et al. "BINAP/1,4-diamine-ruthenium(II) complexes for efficient asymmetric hydrogenation of 1-tetralones and analogues." Organic letters vol. 6,16 (2004): 2681-3. doi: https://doi.org/10.1021/ol049157c
Ohkuma T, Hattori T, Ooka H, Inoue T, Noyori R. BINAP/1,4-diamine-ruthenium(II) complexes for efficient asymmetric hydrogenation of 1-tetralones and analogues. Org Lett. 2004 Aug 05;6(16):2681-3. doi: 10.1021/ol049157c. PMID: 15281743.
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Novel chalcone-based fluorescent human histamine h(3) receptor ligands as pharmacological tools.

Frontiers in systems neuroscience

Tomasch M, Schwed JS, Weizel L, Stark H.
PMID: 22470321
Front Syst Neurosci. 2012 Mar 26;6:14. doi: 10.3389/fnsys.2012.00014. eCollection 2012.

Novel fluorescent chalcone-based ligands at human histamine H(3) receptors (hH(3)R) have been designed, synthesized, and characterized. Compounds described are non-imidazole analogs of ciproxifan with a tetralone motif. Tetralones as chemical precursors and related fluorescent chalcones exhibit affinities at hH(3)R...

Cite
Tomasch M, Schwed JS, Weizel L, et al. Novel chalcone-based fluorescent human histamine h(3) receptor ligands as pharmacological tools. Front Syst Neurosci. 2012;6:14doi: 10.3389/fnsys.2012.00014.
Tomasch, M., Schwed, J. S., Weizel, L., & Stark, H. (2012). Novel chalcone-based fluorescent human histamine h(3) receptor ligands as pharmacological tools. Frontiers in systems neuroscience, 614. https://doi.org/10.3389/fnsys.2012.00014
Tomasch, Miriam, et al. "Novel chalcone-based fluorescent human histamine h(3) receptor ligands as pharmacological tools." Frontiers in systems neuroscience vol. 6 (2012): 14. doi: https://doi.org/10.3389/fnsys.2012.00014
Tomasch M, Schwed JS, Weizel L, Stark H. Novel chalcone-based fluorescent human histamine h(3) receptor ligands as pharmacological tools. Front Syst Neurosci. 2012 Mar 26;6:14. doi: 10.3389/fnsys.2012.00014. eCollection 2012. PMID: 22470321; PMCID: PMC3312100.
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