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Ultrasound-assisted facile one-pot sequential synthesis of novel sulfonamide-isoxazoles using cerium (IV) ammonium nitrate (CAN) as an efficient oxidant in aqueous medium.

Ultrasonics sonochemistry

Alaoui S, Driowya M, Demange L, Benhida R, Bougrin K.
PMID: 28946427
Ultrason Sonochem. 2018 Jan;40:289-297. doi: 10.1016/j.ultsonch.2017.07.019. Epub 2017 Jul 11.

A series of novel 3,5-disubstituted isoxazoles have been synthesized, using a new, green, and versatile "one-pot three-steps" methodology. The key step is an oxidative 1,3-dipolar cycloaddition under ultrasonic irradiation, occurring in aqueous media, and mediated by cerium (IV) ammonium...

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Alaoui S, Driowya M, Demange L, et al. Ultrasound-assisted facile one-pot sequential synthesis of novel sulfonamide-isoxazoles using cerium (IV) ammonium nitrate (CAN) as an efficient oxidant in aqueous medium. Ultrason Sonochem. 2017;40:289-297doi: 10.1016/j.ultsonch.2017.07.019.
Alaoui, S., Driowya, M., Demange, L., Benhida, R., & Bougrin, K. (2018). Ultrasound-assisted facile one-pot sequential synthesis of novel sulfonamide-isoxazoles using cerium (IV) ammonium nitrate (CAN) as an efficient oxidant in aqueous medium. Ultrasonics sonochemistry, 40289-297. https://doi.org/10.1016/j.ultsonch.2017.07.019
Alaoui, Soukaina, et al. "Ultrasound-assisted facile one-pot sequential synthesis of novel sulfonamide-isoxazoles using cerium (IV) ammonium nitrate (CAN) as an efficient oxidant in aqueous medium." Ultrasonics sonochemistry vol. 40 (2018): 289-297. doi: https://doi.org/10.1016/j.ultsonch.2017.07.019
Alaoui S, Driowya M, Demange L, Benhida R, Bougrin K. Ultrasound-assisted facile one-pot sequential synthesis of novel sulfonamide-isoxazoles using cerium (IV) ammonium nitrate (CAN) as an efficient oxidant in aqueous medium. Ultrason Sonochem. 2018 Jan;40:289-297. doi: 10.1016/j.ultsonch.2017.07.019. Epub 2017 Jul 11. PMID: 28946427.
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tert-Butyl Nitrite-Mediated Domino Synthesis of Isoxazolines and Isoxazoles from Terminal Aryl Alkenes and Alkynes.

The Journal of organic chemistry

Sau P, Santra SK, Rakshit A, Patel BK.
PMID: 28521105
J Org Chem. 2017 Jun 16;82(12):6358-6365. doi: 10.1021/acs.joc.7b00946. Epub 2017 May 25.

A sequential construction of C-C, C-O, C═N, and C═O bonds from alkenes leading to the direct synthesis of isoxazolines in the presence of tert-butyl nitrite, quinoline, and the Sc(OTf)

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Sau P, Santra SK, Rakshit A, et al. tert-Butyl Nitrite-Mediated Domino Synthesis of Isoxazolines and Isoxazoles from Terminal Aryl Alkenes and Alkynes. J Org Chem. 2017;82(12):6358-6365doi: 10.1021/acs.joc.7b00946.
Sau, P., Santra, S. K., Rakshit, A., & Patel, B. K. (2017). tert-Butyl Nitrite-Mediated Domino Synthesis of Isoxazolines and Isoxazoles from Terminal Aryl Alkenes and Alkynes. The Journal of organic chemistry, 82(12), 6358-6365. https://doi.org/10.1021/acs.joc.7b00946
Sau, Prasenjit, et al. "tert-Butyl Nitrite-Mediated Domino Synthesis of Isoxazolines and Isoxazoles from Terminal Aryl Alkenes and Alkynes." The Journal of organic chemistry vol. 82,12 (2017): 6358-6365. doi: https://doi.org/10.1021/acs.joc.7b00946
Sau P, Santra SK, Rakshit A, Patel BK. tert-Butyl Nitrite-Mediated Domino Synthesis of Isoxazolines and Isoxazoles from Terminal Aryl Alkenes and Alkynes. J Org Chem. 2017 Jun 16;82(12):6358-6365. doi: 10.1021/acs.joc.7b00946. Epub 2017 May 25. PMID: 28521105.
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Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines.

Chemistry Central journal

Zaki YH, Sayed AR, Elroby SA.
PMID: 27042207
Chem Cent J. 2016 Apr 01;10:17. doi: 10.1186/s13065-016-0163-2. eCollection 2016.

BACKGROUND: Isoxazoles exhibit interesting biological activities, and the 1,3-dipolar cycloaddition(13DC) reactions play an important role in both mechanistic and synthetic organic chemistry. Pyrazoles and annulated pyrazoles exhibit some diverse biological activities. They are used as antipyretic, analgesic drugs, tranquilizing,...

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Zaki YH, Sayed AR, Elroby SA. Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines. Chem Cent J. 2016;10:17doi: 10.1186/s13065-016-0163-2.
Zaki, Y. H., Sayed, A. R., & Elroby, S. A. (2016). Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines. Chemistry Central journal, 1017. https://doi.org/10.1186/s13065-016-0163-2
Zaki, Yasser Hassan, et al. "Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines." Chemistry Central journal vol. 10 (2016): 17. doi: https://doi.org/10.1186/s13065-016-0163-2
Zaki YH, Sayed AR, Elroby SA. Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines. Chem Cent J. 2016 Apr 01;10:17. doi: 10.1186/s13065-016-0163-2. eCollection 2016. PMID: 27042207; PMCID: PMC4818429.
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Recent advances in transition-metal-catalyzed reactions of alkynes with isoxazoles.

Organic & biomolecular chemistry

Li L, Tan TD, Zhang YQ, Liu X, Ye LW.
PMID: 28875211
Org Biomol Chem. 2017 Oct 18;15(40):8483-8492. doi: 10.1039/c7ob01895a.

Isoxazoles, as masked 1,3-dicarbonyl equivalents, have proven to be versatile building blocks and pivotal intermediates for the construction of a variety of useful azacycles with molecular complexity. As a result, a range of new reactions have been discovered based...

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Li L, Tan TD, Zhang YQ, et al. Recent advances in transition-metal-catalyzed reactions of alkynes with isoxazoles. Org Biomol Chem. 2017;15(40):8483-8492doi: 10.1039/c7ob01895a.
Li, L., Tan, T. D., Zhang, Y. Q., Liu, X., & Ye, L. W. (2017). Recent advances in transition-metal-catalyzed reactions of alkynes with isoxazoles. Organic & biomolecular chemistry, 15(40), 8483-8492. https://doi.org/10.1039/c7ob01895a
Li, Long, et al. "Recent advances in transition-metal-catalyzed reactions of alkynes with isoxazoles." Organic & biomolecular chemistry vol. 15,40 (2017): 8483-8492. doi: https://doi.org/10.1039/c7ob01895a
Li L, Tan TD, Zhang YQ, Liu X, Ye LW. Recent advances in transition-metal-catalyzed reactions of alkynes with isoxazoles. Org Biomol Chem. 2017 Oct 18;15(40):8483-8492. doi: 10.1039/c7ob01895a. PMID: 28875211.
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Facile construction and divergent transformation of polycyclic isoxazoles: direct access to polyketide architectures.

Organic letters

Bode JW, Hachisu Y, Matsuura T, Suzuki K.
PMID: 12583726
Org Lett. 2003 Feb 20;5(4):391-4. doi: 10.1021/ol027283f.

[reaction: see text] Base-promoted cyclocondensation of C-chloro oximes with cyclic 1,3-diketones affords functionalized isoxazoles in good yield and under convenient reaction conditions. This process enables the synthesis of highly substituted products with notable functional group tolerance. The products obtained...

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Bode JW, Hachisu Y, Matsuura T, et al. Facile construction and divergent transformation of polycyclic isoxazoles: direct access to polyketide architectures. Org Lett. 2003;5(4):391-4doi: 10.1021/ol027283f.
Bode, J. W., Hachisu, Y., Matsuura, T., & Suzuki, K. (2003). Facile construction and divergent transformation of polycyclic isoxazoles: direct access to polyketide architectures. Organic letters, 5(4), 391-4. https://doi.org/10.1021/ol027283f
Bode, Jeffrey W, et al. "Facile construction and divergent transformation of polycyclic isoxazoles: direct access to polyketide architectures." Organic letters vol. 5,4 (2003): 391-4. doi: https://doi.org/10.1021/ol027283f
Bode JW, Hachisu Y, Matsuura T, Suzuki K. Facile construction and divergent transformation of polycyclic isoxazoles: direct access to polyketide architectures. Org Lett. 2003 Feb 20;5(4):391-4. doi: 10.1021/ol027283f. PMID: 12583726.
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Isoxazole --> benzisoxazole rearrangement promoted cascade reactions affording stereodefined polycycles.

Organic letters

Bode JW, Uesuka H, Suzuki K.
PMID: 12583727
Org Lett. 2003 Feb 20;5(4):395-8. doi: 10.1021/ol0272848.

[reaction: see text] A new chemo-, regio-, and stereoselective cascade reaction features a novel isoxazole --> benzisoxazole rearrangement and affords highly functionalized, differentially protected compounds. The products of this reaction are directly converted to a number of complex, structurally...

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Bode JW, Uesuka H, Suzuki K. Isoxazole --> benzisoxazole rearrangement promoted cascade reactions affording stereodefined polycycles. Org Lett. 2003;5(4):395-8doi: 10.1021/ol0272848.
Bode, J. W., Uesuka, H., & Suzuki, K. (2003). Isoxazole --> benzisoxazole rearrangement promoted cascade reactions affording stereodefined polycycles. Organic letters, 5(4), 395-8. https://doi.org/10.1021/ol0272848
Bode, Jeffrey W, et al. "Isoxazole --> benzisoxazole rearrangement promoted cascade reactions affording stereodefined polycycles." Organic letters vol. 5,4 (2003): 395-8. doi: https://doi.org/10.1021/ol0272848
Bode JW, Uesuka H, Suzuki K. Isoxazole --> benzisoxazole rearrangement promoted cascade reactions affording stereodefined polycycles. Org Lett. 2003 Feb 20;5(4):395-8. doi: 10.1021/ol0272848. PMID: 12583727.
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Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids.

Chemistry (Weinheim an der Bergstrasse, Germany)

Zheng H, McDonald R, Hall DG.
PMID: 20373314
Chemistry. 2010 May 10;16(18):5454-60. doi: 10.1002/chem.200903484.

Herein, the concept of boronic acid catalysis (BAC) for the activation of unsaturated carboxylic acids is applied in several classic dipolar [3+2] cycloadditions involving azides, nitrile oxides, and nitrones as partners. These cycloadditions can be used to produce pharmaceutically...

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Zheng H, McDonald R, Hall DG. Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids. Chemistry. 2010;16(18):5454-60doi: 10.1002/chem.200903484.
Zheng, H., McDonald, R., & Hall, D. G. (2010). Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids. Chemistry (Weinheim an der Bergstrasse, Germany), 16(18), 5454-60. https://doi.org/10.1002/chem.200903484
Zheng, Hongchao, et al. "Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 16,18 (2010): 5454-60. doi: https://doi.org/10.1002/chem.200903484
Zheng H, McDonald R, Hall DG. Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids. Chemistry. 2010 May 10;16(18):5454-60. doi: 10.1002/chem.200903484. PMID: 20373314.
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Investigation of facet effects on the catalytic activity of Cu2O nanocrystals for efficient regioselective synthesis of 3,5-disubstituted isoxazoles.

Nanoscale

Chanda K, Rej S, Huang MH.
PMID: 24165690
Nanoscale. 2013 Dec 21;5(24):12494-501. doi: 10.1039/c3nr03790h.

Cubic, octahedral, and rhombic dodecahedral Cu2O nanocrystals bound by respectively {100}, {111}, and {110} facets were successfully employed to catalyze the [3 + 2] cycloaddition reaction for the regioselective synthesis of 3,5-disubstituted isoxazoles. Surfactant-free nanocrystals having the same total...

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Chanda K, Rej S, Huang MH. Investigation of facet effects on the catalytic activity of Cu2O nanocrystals for efficient regioselective synthesis of 3,5-disubstituted isoxazoles. Nanoscale. 2013;5(24):12494-501doi: 10.1039/c3nr03790h.
Chanda, K., Rej, S., & Huang, M. H. (2013). Investigation of facet effects on the catalytic activity of Cu2O nanocrystals for efficient regioselective synthesis of 3,5-disubstituted isoxazoles. Nanoscale, 5(24), 12494-501. https://doi.org/10.1039/c3nr03790h
Chanda, Kaushik, et al. "Investigation of facet effects on the catalytic activity of Cu2O nanocrystals for efficient regioselective synthesis of 3,5-disubstituted isoxazoles." Nanoscale vol. 5,24 (2013): 12494-501. doi: https://doi.org/10.1039/c3nr03790h
Chanda K, Rej S, Huang MH. Investigation of facet effects on the catalytic activity of Cu2O nanocrystals for efficient regioselective synthesis of 3,5-disubstituted isoxazoles. Nanoscale. 2013 Dec 21;5(24):12494-501. doi: 10.1039/c3nr03790h. PMID: 24165690.
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Preparation and rearrangement of N-vinyl nitrones: synthesis of spiroisoxazolines and fluorene-tethered isoxazoles.

Organic letters

Mo DL, Wink DA, Anderson LL.
PMID: 23046082
Org Lett. 2012 Oct 19;14(20):5180-3. doi: 10.1021/ol3022885. Epub 2012 Oct 09.

N-Vinyl nitrones derived from fluorenone have been prepared via a copper-mediated coupling between fluorenone oxime and vinyl boronic acids. These compounds undergo subsequent rearrangement and addition reactions that are distinct from the traditional [3 + 2] cycloaddition reactivity of...

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Mo DL, Wink DA, Anderson LL. Preparation and rearrangement of N-vinyl nitrones: synthesis of spiroisoxazolines and fluorene-tethered isoxazoles. Org Lett. 2012;14(20):5180-3doi: 10.1021/ol3022885.
Mo, D. L., Wink, D. A., & Anderson, L. L. (2012). Preparation and rearrangement of N-vinyl nitrones: synthesis of spiroisoxazolines and fluorene-tethered isoxazoles. Organic letters, 14(20), 5180-3. https://doi.org/10.1021/ol3022885
Mo, Dong-Liang, et al. "Preparation and rearrangement of N-vinyl nitrones: synthesis of spiroisoxazolines and fluorene-tethered isoxazoles." Organic letters vol. 14,20 (2012): 5180-3. doi: https://doi.org/10.1021/ol3022885
Mo DL, Wink DA, Anderson LL. Preparation and rearrangement of N-vinyl nitrones: synthesis of spiroisoxazolines and fluorene-tethered isoxazoles. Org Lett. 2012 Oct 19;14(20):5180-3. doi: 10.1021/ol3022885. Epub 2012 Oct 09. PMID: 23046082.
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Zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an unprecedented 1,2-sulfur migration.

Chemical communications (Cambridge, England)

Zhu XQ, Sun Q, Zhang ZX, Zhou B, Xie PX, Shen WB, Lu X, Zhou JM, Ye LW.
PMID: 29789833
Chem Commun (Camb). 2018 Jul 03;54(54):7435-7438. doi: 10.1039/c8cc03140a.

A novel zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an unprecedented 1,2-sulfur migration has been developed, which represents the first example of a non-noble metal-catalyzed reaction between isoxazoles and alkynes. This method allows the facile and atom-economical synthesis...

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Zhu XQ, Sun Q, Zhang ZX, et al. Zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an unprecedented 1,2-sulfur migration. Chem Commun (Camb). 2018;54(54):7435-7438doi: 10.1039/c8cc03140a.
Zhu, X. Q., Sun, Q., Zhang, Z. X., Zhou, B., Xie, P. X., Shen, W. B., Lu, X., Zhou, J. M., & Ye, L. W. (2018). Zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an unprecedented 1,2-sulfur migration. Chemical communications (Cambridge, England), 54(54), 7435-7438. https://doi.org/10.1039/c8cc03140a
Zhu, Xin-Qi, et al. "Zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an unprecedented 1,2-sulfur migration." Chemical communications (Cambridge, England) vol. 54,54 (2018): 7435-7438. doi: https://doi.org/10.1039/c8cc03140a
Zhu XQ, Sun Q, Zhang ZX, Zhou B, Xie PX, Shen WB, Lu X, Zhou JM, Ye LW. Zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an unprecedented 1,2-sulfur migration. Chem Commun (Camb). 2018 Jul 03;54(54):7435-7438. doi: 10.1039/c8cc03140a. PMID: 29789833.
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Gold-Catalyzed [4 + 1]-Annulation Reactions between 1,4-Diyn-3-ols and Isoxazoles To Construct a Pyrrole Core.

Organic letters

Kardile RD, Kale BS, Sharma P, Liu RS.
PMID: 29920102
Org Lett. 2018 Jul 06;20(13):3806-3809. doi: 10.1021/acs.orglett.8b01398. Epub 2018 Jun 19.

This work reports gold-catalyzed [4 + 1]-annulation reactions between 1,4-diyn-3-ols and isoxazoles or benzisoxazoles to yield pyrrole derivatives. The reaction chemoselectivity is controlled by an initial attack of an isoxazole at a less hindered alkyne to form gold carbenes,...

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Kardile RD, Kale BS, Sharma P, et al. Gold-Catalyzed [4 + 1]-Annulation Reactions between 1,4-Diyn-3-ols and Isoxazoles To Construct a Pyrrole Core. Org Lett. 2018;20(13):3806-3809doi: 10.1021/acs.orglett.8b01398.
Kardile, R. D., Kale, B. S., Sharma, P., & Liu, R. S. (2018). Gold-Catalyzed [4 + 1]-Annulation Reactions between 1,4-Diyn-3-ols and Isoxazoles To Construct a Pyrrole Core. Organic letters, 20(13), 3806-3809. https://doi.org/10.1021/acs.orglett.8b01398
Kardile, Rahul Dadabhau, et al. "Gold-Catalyzed [4 + 1]-Annulation Reactions between 1,4-Diyn-3-ols and Isoxazoles To Construct a Pyrrole Core." Organic letters vol. 20,13 (2018): 3806-3809. doi: https://doi.org/10.1021/acs.orglett.8b01398
Kardile RD, Kale BS, Sharma P, Liu RS. Gold-Catalyzed [4 + 1]-Annulation Reactions between 1,4-Diyn-3-ols and Isoxazoles To Construct a Pyrrole Core. Org Lett. 2018 Jul 06;20(13):3806-3809. doi: 10.1021/acs.orglett.8b01398. Epub 2018 Jun 19. PMID: 29920102.
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In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: synthesis of fully substituted isoxazoles.

Organic & biomolecular chemistry

Chen R, Ogunlana AA, Fang S, Long W, Sun H, Bao X, Wan X.
PMID: 29892743
Org Biomol Chem. 2018 Jul 07;16(25):4683-4687. doi: 10.1039/c8ob01067f. Epub 2018 Jun 12.

Herein, we present a novel [3 + 2] cycloaddition reaction of β-keto esters with nitrile oxides, which were generated in situ from copper carbene and tert-butyl nitrite. This three-component reaction provides new methodology for the direct synthesis of fully...

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Chen R, Ogunlana AA, Fang S, et al. In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: synthesis of fully substituted isoxazoles. Org Biomol Chem. 2018;16(25):4683-4687doi: 10.1039/c8ob01067f.
Chen, R., Ogunlana, A. A., Fang, S., Long, W., Sun, H., Bao, X., & Wan, X. (2018). In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: synthesis of fully substituted isoxazoles. Organic & biomolecular chemistry, 16(25), 4683-4687. https://doi.org/10.1039/c8ob01067f
Chen, Rongxiang, et al. "In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: synthesis of fully substituted isoxazoles." Organic & biomolecular chemistry vol. 16,25 (2018): 4683-4687. doi: https://doi.org/10.1039/c8ob01067f
Chen R, Ogunlana AA, Fang S, Long W, Sun H, Bao X, Wan X. In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: synthesis of fully substituted isoxazoles. Org Biomol Chem. 2018 Jul 07;16(25):4683-4687. doi: 10.1039/c8ob01067f. Epub 2018 Jun 12. PMID: 29892743.
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