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Synthesis of Spirocyclic Pyrazolones by Oxidative C-N Bond Formation.

The Journal of organic chemistry

Agejas J, Ortega L.
PMID: 26018762
J Org Chem. 2015 Jun 19;80(12):6509-14. doi: 10.1021/acs.joc.5b00796. Epub 2015 Jun 05.

The two-step synthesis of spirocyclic pyrazolone derivatives from simple and commercially available reagents is described. The unusual reaction of 1,3-dicarbonyls with hydrazines and an iodine-mediated oxidative carbon-nitrogen bond formation, joined in a two-step, one-pot reaction, allows the straightforward synthesis...

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Agejas J, Ortega L. Synthesis of Spirocyclic Pyrazolones by Oxidative C-N Bond Formation. J Org Chem. 2015;80(12):6509-14doi: 10.1021/acs.joc.5b00796.
Agejas, J., & Ortega, L. (2015). Synthesis of Spirocyclic Pyrazolones by Oxidative C-N Bond Formation. The Journal of organic chemistry, 80(12), 6509-14. https://doi.org/10.1021/acs.joc.5b00796
Agejas, Javier, and Ortega, Laura. "Synthesis of Spirocyclic Pyrazolones by Oxidative C-N Bond Formation." The Journal of organic chemistry vol. 80,12 (2015): 6509-14. doi: https://doi.org/10.1021/acs.joc.5b00796
Agejas J, Ortega L. Synthesis of Spirocyclic Pyrazolones by Oxidative C-N Bond Formation. J Org Chem. 2015 Jun 19;80(12):6509-14. doi: 10.1021/acs.joc.5b00796. Epub 2015 Jun 05. PMID: 26018762.
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Design and synthesis of reversible solid-state photochromic pyrazolones by introducing a pyridine ring.

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

Guo J, Zhang Y, Jia D, Guo M, Li Y.
PMID: 27714301
Photochem Photobiol Sci. 2016 Oct 05;15(10):1222-1226. doi: 10.1039/c6pp00119j.

We demonstrate a new strategy for designing reversibility, fatigue resistance and fluorescence switching materials, which are based on pyrazolone derivatives by introducing a pyridine ring. The reversible "on" and "off" modulation of fluorescence emission was up to 95% in...

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Guo J, Zhang Y, Jia D, et al. Design and synthesis of reversible solid-state photochromic pyrazolones by introducing a pyridine ring. Photochem Photobiol Sci. 2016;15(10):1222-1226doi: 10.1039/c6pp00119j.
Guo, J., Zhang, Y., Jia, D., Guo, M., & Li, Y. (2016). Design and synthesis of reversible solid-state photochromic pyrazolones by introducing a pyridine ring. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 15(10), 1222-1226. https://doi.org/10.1039/c6pp00119j
Guo, Jixi, et al. "Design and synthesis of reversible solid-state photochromic pyrazolones by introducing a pyridine ring." Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology vol. 15,10 (2016): 1222-1226. doi: https://doi.org/10.1039/c6pp00119j
Guo J, Zhang Y, Jia D, Guo M, Li Y. Design and synthesis of reversible solid-state photochromic pyrazolones by introducing a pyridine ring. Photochem Photobiol Sci. 2016 Oct 05;15(10):1222-1226. doi: 10.1039/c6pp00119j. PMID: 27714301.
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Asymmetric chlorination of 4-substituted pyrazolones catalyzed by natural cinchona alkaloid.

Chemical communications (Cambridge, England)

Bao X, Wei S, Zou L, He Y, Xue F, Qu J, Wang B.
PMID: 27711284
Chem Commun (Camb). 2016 Sep 15;52(76):11426-11429. doi: 10.1039/c6cc06236a.

A natural quinidine-catalyzed asymmetric chlorination of 4-substituted pyrazolones is developed, affording products with a quaternary chiral chlorine-attached carbon centre in high yield with excellent enantioselectivity. The low catalyst loading (1 mol%), broad substrate scope, and facile and valuable transformation...

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Bao X, Wei S, Zou L, et al. Asymmetric chlorination of 4-substituted pyrazolones catalyzed by natural cinchona alkaloid. Chem Commun (Camb). 2016;52(76):11426-11429doi: 10.1039/c6cc06236a.
Bao, X., Wei, S., Zou, L., He, Y., Xue, F., Qu, J., & Wang, B. (2016). Asymmetric chlorination of 4-substituted pyrazolones catalyzed by natural cinchona alkaloid. Chemical communications (Cambridge, England), 52(76), 11426-11429. https://doi.org/10.1039/c6cc06236a
Bao, Xiaoze, et al. "Asymmetric chlorination of 4-substituted pyrazolones catalyzed by natural cinchona alkaloid." Chemical communications (Cambridge, England) vol. 52,76 (2016): 11426-11429. doi: https://doi.org/10.1039/c6cc06236a
Bao X, Wei S, Zou L, He Y, Xue F, Qu J, Wang B. Asymmetric chlorination of 4-substituted pyrazolones catalyzed by natural cinchona alkaloid. Chem Commun (Camb). 2016 Sep 15;52(76):11426-11429. doi: 10.1039/c6cc06236a. PMID: 27711284.
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Diastereodivergent and Enantioselective Access to Spiroepoxides via Organocatalytic Epoxidation of Unsaturated Pyrazolones.

Organic letters

Meninno S, Roselli A, Capobianco A, Overgaard J, Lattanzi A.
PMID: 28906120
Org Lett. 2017 Oct 06;19(19):5030-5033. doi: 10.1021/acs.orglett.7b02189. Epub 2017 Sep 14.

Readily available chiral amine-thioureas are effective catalysts for the first diastereo- and enantioselective epoxidation of unsaturated pyrazolones. The trans- or cis-spiroepoxides are preferentially obtained in good yield and high to excellent enantioselectivity using an appropriate organocatalyst and tert-butyl hydroperoxide...

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Meninno S, Roselli A, Capobianco A, et al. Diastereodivergent and Enantioselective Access to Spiroepoxides via Organocatalytic Epoxidation of Unsaturated Pyrazolones. Org Lett. 2017;19(19):5030-5033doi: 10.1021/acs.orglett.7b02189.
Meninno, S., Roselli, A., Capobianco, A., Overgaard, J., & Lattanzi, A. (2017). Diastereodivergent and Enantioselective Access to Spiroepoxides via Organocatalytic Epoxidation of Unsaturated Pyrazolones. Organic letters, 19(19), 5030-5033. https://doi.org/10.1021/acs.orglett.7b02189
Meninno, Sara, et al. "Diastereodivergent and Enantioselective Access to Spiroepoxides via Organocatalytic Epoxidation of Unsaturated Pyrazolones." Organic letters vol. 19,19 (2017): 5030-5033. doi: https://doi.org/10.1021/acs.orglett.7b02189
Meninno S, Roselli A, Capobianco A, Overgaard J, Lattanzi A. Diastereodivergent and Enantioselective Access to Spiroepoxides via Organocatalytic Epoxidation of Unsaturated Pyrazolones. Org Lett. 2017 Oct 06;19(19):5030-5033. doi: 10.1021/acs.orglett.7b02189. Epub 2017 Sep 14. PMID: 28906120.
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Asymmetric, Three-Component, One-Pot Synthesis of Spiropyrazolones and 2,5-Chromenediones from Aldol Condensation/NHC-Catalyzed Annulation Reactions.

Chemistry (Weinheim an der Bergstrasse, Germany)

Wang L, Li S, Chauhan P, Hack D, Philipps AR, Puttreddy R, Rissanen K, Raabe G, Enders D.
PMID: 26864437
Chemistry. 2016 Apr 04;22(15):5123-7. doi: 10.1002/chem.201600515. Epub 2016 Feb 18.

A novel one-pot, three-component diastereo- and enantioselective synthesis of spiropyrazolones has been developed involving the aldol condensation of an enal to generate α,β-unsaturated pyrazolones, which react with a second equivalent of enal through an N-heterocyclic carbene (NHC)-catalyzed [3+2] annulation....

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Wang L, Li S, Chauhan P, et al. Asymmetric, Three-Component, One-Pot Synthesis of Spiropyrazolones and 2,5-Chromenediones from Aldol Condensation/NHC-Catalyzed Annulation Reactions. Chemistry. 2016;22(15):5123-7doi: 10.1002/chem.201600515.
Wang, L., Li, S., Chauhan, P., Hack, D., Philipps, A. R., Puttreddy, R., Rissanen, K., Raabe, G., & Enders, D. (2016). Asymmetric, Three-Component, One-Pot Synthesis of Spiropyrazolones and 2,5-Chromenediones from Aldol Condensation/NHC-Catalyzed Annulation Reactions. Chemistry (Weinheim an der Bergstrasse, Germany), 22(15), 5123-7. https://doi.org/10.1002/chem.201600515
Wang, Lei, et al. "Asymmetric, Three-Component, One-Pot Synthesis of Spiropyrazolones and 2,5-Chromenediones from Aldol Condensation/NHC-Catalyzed Annulation Reactions." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,15 (2016): 5123-7. doi: https://doi.org/10.1002/chem.201600515
Wang L, Li S, Chauhan P, Hack D, Philipps AR, Puttreddy R, Rissanen K, Raabe G, Enders D. Asymmetric, Three-Component, One-Pot Synthesis of Spiropyrazolones and 2,5-Chromenediones from Aldol Condensation/NHC-Catalyzed Annulation Reactions. Chemistry. 2016 Apr 04;22(15):5123-7. doi: 10.1002/chem.201600515. Epub 2016 Feb 18. PMID: 26864437.
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Asymmetric synthesis of pyrazoles and pyrazolones employing the reactivity of pyrazolin-5-one derivatives.

Chemical communications (Cambridge, England)

Chauhan P, Mahajan S, Enders D.
PMID: 26178319
Chem Commun (Camb). 2015 Aug 21;51(65):12890-907. doi: 10.1039/c5cc04930j.

Due to the frequent occurrence of the pyrazole core in many important naturally occurring and synthetic molecules, tremendous efforts have been made for their synthesis. The pyrazolin-5-one derivatives have emerged as the most effective substrates for the synthesis of...

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Chauhan P, Mahajan S, Enders D. Asymmetric synthesis of pyrazoles and pyrazolones employing the reactivity of pyrazolin-5-one derivatives. Chem Commun (Camb). 2015;51(65):12890-907doi: 10.1039/c5cc04930j.
Chauhan, P., Mahajan, S., & Enders, D. (2015). Asymmetric synthesis of pyrazoles and pyrazolones employing the reactivity of pyrazolin-5-one derivatives. Chemical communications (Cambridge, England), 51(65), 12890-907. https://doi.org/10.1039/c5cc04930j
Chauhan, Pankaj, et al. "Asymmetric synthesis of pyrazoles and pyrazolones employing the reactivity of pyrazolin-5-one derivatives." Chemical communications (Cambridge, England) vol. 51,65 (2015): 12890-907. doi: https://doi.org/10.1039/c5cc04930j
Chauhan P, Mahajan S, Enders D. Asymmetric synthesis of pyrazoles and pyrazolones employing the reactivity of pyrazolin-5-one derivatives. Chem Commun (Camb). 2015 Aug 21;51(65):12890-907. doi: 10.1039/c5cc04930j. PMID: 26178319.
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Convenient ultrasound mediated synthesis of substituted pyrazolones under solvent-free conditions.

Ultrasonics sonochemistry

Mojtahedi MM, Javadpour M, Abaee MS.
PMID: 18387840
Ultrason Sonochem. 2008 Jul;15(5):828-32. doi: 10.1016/j.ultsonch.2008.02.010. Epub 2008 Feb 29.

Smooth condensation of hydrazine derivatives with various beta-keto esters was performed under solvent-free conditions by using ultrasound irradiation to facilitate the formation of pyrazolone derivatives in good to excellent amounts within very short time periods.

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Mojtahedi MM, Javadpour M, Abaee MS. Convenient ultrasound mediated synthesis of substituted pyrazolones under solvent-free conditions. Ultrason Sonochem. 2008;15(5):828-32doi: 10.1016/j.ultsonch.2008.02.010.
Mojtahedi, M. M., Javadpour, M., & Abaee, M. S. (2008). Convenient ultrasound mediated synthesis of substituted pyrazolones under solvent-free conditions. Ultrasonics sonochemistry, 15(5), 828-32. https://doi.org/10.1016/j.ultsonch.2008.02.010
Mojtahedi, Mohammad M, et al. "Convenient ultrasound mediated synthesis of substituted pyrazolones under solvent-free conditions." Ultrasonics sonochemistry vol. 15,5 (2008): 828-32. doi: https://doi.org/10.1016/j.ultsonch.2008.02.010
Mojtahedi MM, Javadpour M, Abaee MS. Convenient ultrasound mediated synthesis of substituted pyrazolones under solvent-free conditions. Ultrason Sonochem. 2008 Jul;15(5):828-32. doi: 10.1016/j.ultsonch.2008.02.010. Epub 2008 Feb 29. PMID: 18387840.
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Reactions of 1,3-Diphenyl-2-pyrazolin-5-one and 4-Amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one. Synthesis of Some New Pyrazoles and Pyrazolones.

Acta chimica Slovenica

El-Metwally S, Khalil AKh.
PMID: 24061901
Acta Chim Slov. 2010 Dec;57(4):941-7.

1,3-Diphenyl-2-pyrazolin-5-one 1 was converted to 5-azido-4-formylpyrazolone 3 which is used as the key starting compounds of some new pyrazole derivatives 4-9. Also, 4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one 10 is coupled with some diazonium salts to give coloured products 11, and reacted with isocyanates...

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El-Metwally S, Khalil AKh. Reactions of 1,3-Diphenyl-2-pyrazolin-5-one and 4-Amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one. Synthesis of Some New Pyrazoles and Pyrazolones. Acta Chim Slov. 2010;57(4):941-7
El-Metwally, S., & Khalil, A. K. h. (2010). Reactions of 1,3-Diphenyl-2-pyrazolin-5-one and 4-Amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one. Synthesis of Some New Pyrazoles and Pyrazolones. Acta chimica Slovenica, 57(4), 941-7.
El-Metwally, Souad, and Khalil, Ali Kh. "Reactions of 1,3-Diphenyl-2-pyrazolin-5-one and 4-Amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one. Synthesis of Some New Pyrazoles and Pyrazolones." Acta chimica Slovenica vol. 57,4 (2010): 941-7.
El-Metwally S, Khalil AKh. Reactions of 1,3-Diphenyl-2-pyrazolin-5-one and 4-Amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one. Synthesis of Some New Pyrazoles and Pyrazolones. Acta Chim Slov. 2010 Dec;57(4):941-7. PMID: 24061901.
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Copper-catalyzed acylation of pyrazolones with aldehydes to afford 4-acylpyrazolones.

Organic & biomolecular chemistry

Xiao Y, Wu X, Teng J, Sun S, Yu JT, Cheng J.
PMID: 31372617
Org Biomol Chem. 2019 Aug 28;17(32):7552-7557. doi: 10.1039/c9ob01486a. Epub 2019 Aug 02.

Copper-catalyzed direct acylation of the alkenyl C-H bond in 1,2-dihydro-3H-pyrazol-3-ones has been developed, affording a series of 4-acylpyrazolones in moderate to good yields. Notably, this protocol involves readily accessible substrates and reagents, which have good functional group tolerance leading...

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Xiao Y, Wu X, Teng J, et al. Copper-catalyzed acylation of pyrazolones with aldehydes to afford 4-acylpyrazolones. Org Biomol Chem. 2019;17(32):7552-7557doi: 10.1039/c9ob01486a.
Xiao, Y., Wu, X., Teng, J., Sun, S., Yu, J. T., & Cheng, J. (2019). Copper-catalyzed acylation of pyrazolones with aldehydes to afford 4-acylpyrazolones. Organic & biomolecular chemistry, 17(32), 7552-7557. https://doi.org/10.1039/c9ob01486a
Xiao, Yan, et al. "Copper-catalyzed acylation of pyrazolones with aldehydes to afford 4-acylpyrazolones." Organic & biomolecular chemistry vol. 17,32 (2019): 7552-7557. doi: https://doi.org/10.1039/c9ob01486a
Xiao Y, Wu X, Teng J, Sun S, Yu JT, Cheng J. Copper-catalyzed acylation of pyrazolones with aldehydes to afford 4-acylpyrazolones. Org Biomol Chem. 2019 Aug 28;17(32):7552-7557. doi: 10.1039/c9ob01486a. Epub 2019 Aug 02. PMID: 31372617.
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Chemo- and Stereoselective Cross Rauhut-Currier-Type Reaction of Tri-substituted Alkenes Containing Trifluoromethyl Groups.

Chemistry (Weinheim an der Bergstrasse, Germany)

He XH, Yang L, Ji YL, Zhao Q, Yang MC, Huang W, Peng C, Han B.
PMID: 29193431
Chemistry. 2018 Feb 06;24(8):1947-1955. doi: 10.1002/chem.201705010. Epub 2018 Jan 10.

A chemoselective cross Rauhut-Currier-type reaction has been developed involving a tri-substituted alkene (trifluoromethyl-containing acrylonitrile derivative) with a di- or tri-substituted alkene to yield tetra-substituted double bonds in RC-type products. This approach can support the synthesis of trifluoromethylated tetra-substituted olefins...

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He XH, Yang L, Ji YL, et al. Chemo- and Stereoselective Cross Rauhut-Currier-Type Reaction of Tri-substituted Alkenes Containing Trifluoromethyl Groups. Chemistry. 2018;24(8):1947-1955doi: 10.1002/chem.201705010.
He, X. H., Yang, L., Ji, Y. L., Zhao, Q., Yang, M. C., Huang, W., Peng, C., & Han, B. (2018). Chemo- and Stereoselective Cross Rauhut-Currier-Type Reaction of Tri-substituted Alkenes Containing Trifluoromethyl Groups. Chemistry (Weinheim an der Bergstrasse, Germany), 24(8), 1947-1955. https://doi.org/10.1002/chem.201705010
He, Xiang-Hong, et al. "Chemo- and Stereoselective Cross Rauhut-Currier-Type Reaction of Tri-substituted Alkenes Containing Trifluoromethyl Groups." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 24,8 (2018): 1947-1955. doi: https://doi.org/10.1002/chem.201705010
He XH, Yang L, Ji YL, Zhao Q, Yang MC, Huang W, Peng C, Han B. Chemo- and Stereoselective Cross Rauhut-Currier-Type Reaction of Tri-substituted Alkenes Containing Trifluoromethyl Groups. Chemistry. 2018 Feb 06;24(8):1947-1955. doi: 10.1002/chem.201705010. Epub 2018 Jan 10. PMID: 29193431.
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Lewis-Base-Catalyzed [1 + 2 + 2] Annulation Reaction of Morita-Baylis-Hillman Carbonates with Unsaturated Pyrazolones: Construction of All-Stereogenic Carbon Cyclopentane-Fused Dispiropyrazolones.

The Journal of organic chemistry

Liang JY, Shen SJ, Chai XQ, Lv T.
PMID: 30226379
J Org Chem. 2018 Oct 19;83(20):12744-12752. doi: 10.1021/acs.joc.8b02188. Epub 2018 Sep 28.

The first Lewis-base-catalyzed unexpected [1 + 2 + 2] annulation reaction between Morita-Baylis-Hillman carbonates and unsaturated pyrazolones was developed. The multicyclic cyclopentane-fused dispiropyrazolone constructions containing five contiguous stereogenic centers, including two spiro quaternary centers, were prepared with excellent yields...

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Liang JY, Shen SJ, Chai XQ, et al. Lewis-Base-Catalyzed [1 + 2 + 2] Annulation Reaction of Morita-Baylis-Hillman Carbonates with Unsaturated Pyrazolones: Construction of All-Stereogenic Carbon Cyclopentane-Fused Dispiropyrazolones. J Org Chem. 2018;83(20):12744-12752doi: 10.1021/acs.joc.8b02188.
Liang, J. Y., Shen, S. J., Chai, X. Q., & Lv, T. (2018). Lewis-Base-Catalyzed [1 + 2 + 2] Annulation Reaction of Morita-Baylis-Hillman Carbonates with Unsaturated Pyrazolones: Construction of All-Stereogenic Carbon Cyclopentane-Fused Dispiropyrazolones. The Journal of organic chemistry, 83(20), 12744-12752. https://doi.org/10.1021/acs.joc.8b02188
Liang, Jin-Yan, et al. "Lewis-Base-Catalyzed [1 + 2 + 2] Annulation Reaction of Morita-Baylis-Hillman Carbonates with Unsaturated Pyrazolones: Construction of All-Stereogenic Carbon Cyclopentane-Fused Dispiropyrazolones." The Journal of organic chemistry vol. 83,20 (2018): 12744-12752. doi: https://doi.org/10.1021/acs.joc.8b02188
Liang JY, Shen SJ, Chai XQ, Lv T. Lewis-Base-Catalyzed [1 + 2 + 2] Annulation Reaction of Morita-Baylis-Hillman Carbonates with Unsaturated Pyrazolones: Construction of All-Stereogenic Carbon Cyclopentane-Fused Dispiropyrazolones. J Org Chem. 2018 Oct 19;83(20):12744-12752. doi: 10.1021/acs.joc.8b02188. Epub 2018 Sep 28. PMID: 30226379.
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Synthesis of Spiropentadiene Pyrazolones by Rh(III)-Catalyzed Formal sp.

Organic letters

Zheng J, Li P, Gu M, Lin A, Yao H.
PMID: 28508646
Org Lett. 2017 Jun 02;19(11):2829-2832. doi: 10.1021/acs.orglett.7b00930. Epub 2017 May 16.

A Rh-catalyzed enol-directed formal sp

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Zheng J, Li P, Gu M, et al. Synthesis of Spiropentadiene Pyrazolones by Rh(III)-Catalyzed Formal sp. Org Lett. 2017;19(11):2829-2832doi: 10.1021/acs.orglett.7b00930.
Zheng, J., Li, P., Gu, M., Lin, A., & Yao, H. (2017). Synthesis of Spiropentadiene Pyrazolones by Rh(III)-Catalyzed Formal sp. Organic letters, 19(11), 2829-2832. https://doi.org/10.1021/acs.orglett.7b00930
Zheng, Jiuan, et al. "Synthesis of Spiropentadiene Pyrazolones by Rh(III)-Catalyzed Formal sp." Organic letters vol. 19,11 (2017): 2829-2832. doi: https://doi.org/10.1021/acs.orglett.7b00930
Zheng J, Li P, Gu M, Lin A, Yao H. Synthesis of Spiropentadiene Pyrazolones by Rh(III)-Catalyzed Formal sp. Org Lett. 2017 Jun 02;19(11):2829-2832. doi: 10.1021/acs.orglett.7b00930. Epub 2017 May 16. PMID: 28508646.
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Showing 1 to 12 of 116 entries