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Phosphine-Initiated General-Base-Catalyzed Quinolone Synthesis.

Asian journal of organic chemistry

Khong S, Kwon O.
PMID: 26207200
Asian J Org Chem. 2014 Apr;3(4):453-457. doi: 10.1002/ajoc.201402039.

Phosphinocatalysis provides a new approach toward 3-substituted-4-quinolones. A simple procedure, which uses Ph

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Khong S, Kwon O. Phosphine-Initiated General-Base-Catalyzed Quinolone Synthesis. Asian J Org Chem. 2014;3(4):453-457doi: 10.1002/ajoc.201402039.
Khong, S., & Kwon, O. (2014). Phosphine-Initiated General-Base-Catalyzed Quinolone Synthesis. Asian journal of organic chemistry, 3(4), 453-457. https://doi.org/10.1002/ajoc.201402039
Khong, San, and Kwon, Ohyun. "Phosphine-Initiated General-Base-Catalyzed Quinolone Synthesis." Asian journal of organic chemistry vol. 3,4 (2014): 453-457. doi: https://doi.org/10.1002/ajoc.201402039
Khong S, Kwon O. Phosphine-Initiated General-Base-Catalyzed Quinolone Synthesis. Asian J Org Chem. 2014 Apr;3(4):453-457. doi: 10.1002/ajoc.201402039. PMID: 26207200; PMCID: PMC4509642.
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Aryliminopropadienone-C-Amidoketenimine- Amidinoketene-2-Aminoquinolone Cascades and the Ynamine-Isocyanate Reaction.

The Journal of organic chemistry

Wentrup C, Rao VV, Frank W, Fulloon BE, Moloney DW, Mosandl T.
PMID: 11674488
J Org Chem. 1999 May 14;64(10):3608-3619. doi: 10.1021/jo982471y.

Imidoylketenes 11 and oxoketenimines 12 are generated by flash vacuum thermolysis of Meldrum's acid derivatives 9, pyrrolediones 17 and 18, and triazole 19 and are observed by IR spectroscopy. Ketenimine-3-carboxylic acid esters 12a are isolable at room temperature. Ketenes...

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Wentrup C, Rao VV, Frank W, et al. Aryliminopropadienone-C-Amidoketenimine- Amidinoketene-2-Aminoquinolone Cascades and the Ynamine-Isocyanate Reaction. J Org Chem. 1999;64(10):3608-3619doi: 10.1021/jo982471y.
Wentrup, C., Rao, V. V., Frank, W., Fulloon, B. E., Moloney, D. W., & Mosandl, T. (1999). Aryliminopropadienone-C-Amidoketenimine- Amidinoketene-2-Aminoquinolone Cascades and the Ynamine-Isocyanate Reaction. The Journal of organic chemistry, 64(10), 3608-3619. https://doi.org/10.1021/jo982471y
Wentrup, Curt, et al. "Aryliminopropadienone-C-Amidoketenimine- Amidinoketene-2-Aminoquinolone Cascades and the Ynamine-Isocyanate Reaction." The Journal of organic chemistry vol. 64,10 (1999): 3608-3619. doi: https://doi.org/10.1021/jo982471y
Wentrup C, Rao VV, Frank W, Fulloon BE, Moloney DW, Mosandl T. Aryliminopropadienone-C-Amidoketenimine- Amidinoketene-2-Aminoquinolone Cascades and the Ynamine-Isocyanate Reaction. J Org Chem. 1999 May 14;64(10):3608-3619. doi: 10.1021/jo982471y. PMID: 11674488.
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Asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones by rhodium-catalyzed 1,4-addition of arylzinc reagents in the presence of chlorotrimethylsilane.

Organic letters

Shintani R, Yamagami T, Kimura T, Hayashi T.
PMID: 16268567
Org Lett. 2005 Nov 10;7(23):5317-9. doi: 10.1021/ol052257d.

[reaction: see text] The first catalytic asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones has been developed by way of a rhodium-catalyzed 1,4-addition of arylzinc reagents to 4-quinolones. These 1,4-adducts can be obtained with high enantioselectivity by the use of (R)-binap as a...

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Shintani R, Yamagami T, Kimura T, et al. Asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones by rhodium-catalyzed 1,4-addition of arylzinc reagents in the presence of chlorotrimethylsilane. Org Lett. 2005;7(23):5317-9doi: 10.1021/ol052257d.
Shintani, R., Yamagami, T., Kimura, T., & Hayashi, T. (2005). Asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones by rhodium-catalyzed 1,4-addition of arylzinc reagents in the presence of chlorotrimethylsilane. Organic letters, 7(23), 5317-9. https://doi.org/10.1021/ol052257d
Shintani, Ryo, et al. "Asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones by rhodium-catalyzed 1,4-addition of arylzinc reagents in the presence of chlorotrimethylsilane." Organic letters vol. 7,23 (2005): 5317-9. doi: https://doi.org/10.1021/ol052257d
Shintani R, Yamagami T, Kimura T, Hayashi T. Asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones by rhodium-catalyzed 1,4-addition of arylzinc reagents in the presence of chlorotrimethylsilane. Org Lett. 2005 Nov 10;7(23):5317-9. doi: 10.1021/ol052257d. PMID: 16268567.
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Fluoroquinolones: mechanisms of action and resistance.

International journal of antimicrobial agents

Bryskier A.
PMID: 18611533
Int J Antimicrob Agents. 1993;2(3):151-83. doi: 10.1016/0924-8579(93)90052-7.

The mechanism of action and the mechanism of resistance of the 4-quinolones are complex and poorly understood. The first barrier these molecules must cross is the bacterial outer membrane. In gram-negative species, 4-quinolones pass through either the porins or...

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Bryskier A. Fluoroquinolones: mechanisms of action and resistance. Int J Antimicrob Agents. 1993;2(3):151-83doi: 10.1016/0924-8579(93)90052-7.
Bryskier, A. (1993). Fluoroquinolones: mechanisms of action and resistance. International journal of antimicrobial agents, 2(3), 151-83. https://doi.org/10.1016/0924-8579(93)90052-7
Bryskier, A. "Fluoroquinolones: mechanisms of action and resistance." International journal of antimicrobial agents vol. 2,3 (1993): 151-83. doi: https://doi.org/10.1016/0924-8579(93)90052-7
Bryskier A. Fluoroquinolones: mechanisms of action and resistance. Int J Antimicrob Agents. 1993;2(3):151-83. doi: 10.1016/0924-8579(93)90052-7. PMID: 18611533.
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Divergent Synthesis of Quinolones and Dihydroepindolidiones via Cu(I)-Catalyzed Cyclization of Anilines with Alkynes.

Organic letters

Xu X, Sun R, Zhang S, Zhang X, Yi W.
PMID: 29558143
Org Lett. 2018 Apr 06;20(7):1893-1897. doi: 10.1021/acs.orglett.8b00436. Epub 2018 Mar 20.

A unique and efficient method for one-pot synthesis of diverse 4-quinolones from simple and readily available primary anilines and alkynes via Cu(I)-catalyzed direct cyclization has been developed. The (thio)phenols were also found to visible substrates for this reaction. Moreover,...

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Xu X, Sun R, Zhang S, et al. Divergent Synthesis of Quinolones and Dihydroepindolidiones via Cu(I)-Catalyzed Cyclization of Anilines with Alkynes. Org Lett. 2018;20(7):1893-1897doi: 10.1021/acs.orglett.8b00436.
Xu, X., Sun, R., Zhang, S., Zhang, X., & Yi, W. (2018). Divergent Synthesis of Quinolones and Dihydroepindolidiones via Cu(I)-Catalyzed Cyclization of Anilines with Alkynes. Organic letters, 20(7), 1893-1897. https://doi.org/10.1021/acs.orglett.8b00436
Xu, Xuefeng, et al. "Divergent Synthesis of Quinolones and Dihydroepindolidiones via Cu(I)-Catalyzed Cyclization of Anilines with Alkynes." Organic letters vol. 20,7 (2018): 1893-1897. doi: https://doi.org/10.1021/acs.orglett.8b00436
Xu X, Sun R, Zhang S, Zhang X, Yi W. Divergent Synthesis of Quinolones and Dihydroepindolidiones via Cu(I)-Catalyzed Cyclization of Anilines with Alkynes. Org Lett. 2018 Apr 06;20(7):1893-1897. doi: 10.1021/acs.orglett.8b00436. Epub 2018 Mar 20. PMID: 29558143.
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Metal-Free Radical Oxidative Cyclization of o-Azidoaryl Acetylenic Ketones with Sulfinic Acids To Access Sulfone-Containing 4-Quinolones.

The Journal of organic chemistry

Zhou N, Yan Z, Zhang H, Wu Z, Zhu C.
PMID: 27978760
J Org Chem. 2016 Dec 16;81(24):12181-12188. doi: 10.1021/acs.joc.6b01847. Epub 2016 Dec 06.

A novel one-pot synthesis of sulfone-containing 4-quinolones with easily available sulfinic acids as sulfonylating precursors is described. This reaction is characterized by mild reaction conditions, high functional-group tolerance and amenability to gram-scale synthesis.

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Zhou N, Yan Z, Zhang H, et al. Metal-Free Radical Oxidative Cyclization of o-Azidoaryl Acetylenic Ketones with Sulfinic Acids To Access Sulfone-Containing 4-Quinolones. J Org Chem. 2016;81(24):12181-12188doi: 10.1021/acs.joc.6b01847.
Zhou, N., Yan, Z., Zhang, H., Wu, Z., & Zhu, C. (2016). Metal-Free Radical Oxidative Cyclization of o-Azidoaryl Acetylenic Ketones with Sulfinic Acids To Access Sulfone-Containing 4-Quinolones. The Journal of organic chemistry, 81(24), 12181-12188. https://doi.org/10.1021/acs.joc.6b01847
Zhou, Nengneng, et al. "Metal-Free Radical Oxidative Cyclization of o-Azidoaryl Acetylenic Ketones with Sulfinic Acids To Access Sulfone-Containing 4-Quinolones." The Journal of organic chemistry vol. 81,24 (2016): 12181-12188. doi: https://doi.org/10.1021/acs.joc.6b01847
Zhou N, Yan Z, Zhang H, Wu Z, Zhu C. Metal-Free Radical Oxidative Cyclization of o-Azidoaryl Acetylenic Ketones with Sulfinic Acids To Access Sulfone-Containing 4-Quinolones. J Org Chem. 2016 Dec 16;81(24):12181-12188. doi: 10.1021/acs.joc.6b01847. Epub 2016 Dec 06. PMID: 27978760.
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Transition-Metal-Catalyzed Regiodivergent and Stereoselective Access to Branched and Linear Allylated 4-Pyridones.

Chemistry (Weinheim an der Bergstrasse, Germany)

Schmidt JP, Li C, Breit B.
PMID: 28370612
Chemistry. 2017 May 11;23(27):6531-6534. doi: 10.1002/chem.201701382. Epub 2017 Apr 13.

A regiodivergent and stereoselective transition-metal-catalyzed addition of 4-pyridones to allenes furnishing N-allylated pyridones is reported. Employing a commercially available chiral rhodium catalyst enabled enantioselective branched-selective allylation. Conversely, an achiral palladium catalyst led to linear-selective N-allylation in high E-selectivities. A...

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Schmidt JP, Li C, Breit B. Transition-Metal-Catalyzed Regiodivergent and Stereoselective Access to Branched and Linear Allylated 4-Pyridones. Chemistry. 2017;23(27):6531-6534doi: 10.1002/chem.201701382.
Schmidt, J. P., Li, C., & Breit, B. (2017). Transition-Metal-Catalyzed Regiodivergent and Stereoselective Access to Branched and Linear Allylated 4-Pyridones. Chemistry (Weinheim an der Bergstrasse, Germany), 23(27), 6531-6534. https://doi.org/10.1002/chem.201701382
Schmidt, Johannes P, et al. "Transition-Metal-Catalyzed Regiodivergent and Stereoselective Access to Branched and Linear Allylated 4-Pyridones." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 23,27 (2017): 6531-6534. doi: https://doi.org/10.1002/chem.201701382
Schmidt JP, Li C, Breit B. Transition-Metal-Catalyzed Regiodivergent and Stereoselective Access to Branched and Linear Allylated 4-Pyridones. Chemistry. 2017 May 11;23(27):6531-6534. doi: 10.1002/chem.201701382. Epub 2017 Apr 13. PMID: 28370612.
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In quest of small-molecules as potent non-competitive inhibitors against influenza.

Bioorganic chemistry

Malbari K, Saha P, Chawla-Sarkar M, Dutta S, Rai S, Joshi M, Kanyalkar M.
PMID: 34243071
Bioorg Chem. 2021 Sep;114:105139. doi: 10.1016/j.bioorg.2021.105139. Epub 2021 Jul 01.

A series of scaffolds namely aurones, 3-indolinones, 4-quinolones and cinnamic acid-piperazine hybrids, was designed, synthesized and investigated in vitro against influenza A/H1N1pdm09 virus. Designed molecules adopted different binding mode i.e., in 430-cavity of neuraminidase, unlike sialic acid and oseltamivir...

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Malbari K, Saha P, Chawla-Sarkar M, et al. In quest of small-molecules as potent non-competitive inhibitors against influenza. Bioorg Chem. 2021;114:105139doi: 10.1016/j.bioorg.2021.105139.
Malbari, K., Saha, P., Chawla-Sarkar, M., Dutta, S., Rai, S., Joshi, M., & Kanyalkar, M. (2021). In quest of small-molecules as potent non-competitive inhibitors against influenza. Bioorganic chemistry, 114105139. https://doi.org/10.1016/j.bioorg.2021.105139
Malbari, Khushboo, et al. "In quest of small-molecules as potent non-competitive inhibitors against influenza." Bioorganic chemistry vol. 114 (2021): 105139. doi: https://doi.org/10.1016/j.bioorg.2021.105139
Malbari K, Saha P, Chawla-Sarkar M, Dutta S, Rai S, Joshi M, Kanyalkar M. In quest of small-molecules as potent non-competitive inhibitors against influenza. Bioorg Chem. 2021 Sep;114:105139. doi: 10.1016/j.bioorg.2021.105139. Epub 2021 Jul 01. PMID: 34243071.
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Hypervalent Iodine(III)-Promoted C3-H Regioselective Halogenation of 4-Quinolones under Mild Conditions.

ACS omega

Yang F, Wang X, Zhao W, Yu F, Yu Z.
PMID: 34926952
ACS Omega. 2021 Nov 29;6(49):34044-34055. doi: 10.1021/acsomega.1c05455. eCollection 2021 Dec 14.

A simple and practical protocol for the C3-H regioselective halogenation of 4-quinolones by the action of potassium halide salt and PIFA/PIDA in good to excellent yields was developed. The current approach provides feasible access to the diversity of C3-halgenated...

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Yang F, Wang X, Zhao W, et al. Hypervalent Iodine(III)-Promoted C3-H Regioselective Halogenation of 4-Quinolones under Mild Conditions. ACS Omega. 2021;6(49):34044-34055doi: 10.1021/acsomega.1c05455.
Yang, F., Wang, X., Zhao, W., Yu, F., & Yu, Z. (2021). Hypervalent Iodine(III)-Promoted C3-H Regioselective Halogenation of 4-Quinolones under Mild Conditions. ACS omega, 6(49), 34044-34055. https://doi.org/10.1021/acsomega.1c05455
Yang, Fang, et al. "Hypervalent Iodine(III)-Promoted C3-H Regioselective Halogenation of 4-Quinolones under Mild Conditions." ACS omega vol. 6,49 (2021): 34044-34055. doi: https://doi.org/10.1021/acsomega.1c05455
Yang F, Wang X, Zhao W, Yu F, Yu Z. Hypervalent Iodine(III)-Promoted C3-H Regioselective Halogenation of 4-Quinolones under Mild Conditions. ACS Omega. 2021 Nov 29;6(49):34044-34055. doi: 10.1021/acsomega.1c05455. eCollection 2021 Dec 14. PMID: 34926952; PMCID: PMC8675166.
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A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones.

Chemical communications (Cambridge, England)

Babu KR, Han W, Chen JB, Li Y, Tang Y, Zhang W, Xu W, Xu S.
PMID: 32342091
Chem Commun (Camb). 2020 Jun 02;56(44):5909-5912. doi: 10.1039/d0cc01401j.

A three-component reaction between one molecule of phosphorus ylides (P-ylides) and two molecules of isocyanates for the rapid assembly of 2-amino-3-carboxylate-4-quinolones is described. The mechanism may involve the addition of a P-ylide to an isocyanate followed by 1,3-H shift...

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Babu KR, Han W, Chen JB, et al. A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones. Chem Commun (Camb). 2020;56(44):5909-5912doi: 10.1039/d0cc01401j.
Babu, K. R., Han, W., Chen, J. B., Li, Y., Tang, Y., Zhang, W., Xu, W., & Xu, S. (2020). A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones. Chemical communications (Cambridge, England), 56(44), 5909-5912. https://doi.org/10.1039/d0cc01401j
Babu, Kaki Raveendra, et al. "A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones." Chemical communications (Cambridge, England) vol. 56,44 (2020): 5909-5912. doi: https://doi.org/10.1039/d0cc01401j
Babu KR, Han W, Chen JB, Li Y, Tang Y, Zhang W, Xu W, Xu S. A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones. Chem Commun (Camb). 2020 Jun 02;56(44):5909-5912. doi: 10.1039/d0cc01401j. PMID: 32342091.
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Ketene dithioacetals in the aza-Diels-Alder reaction with N-arylimines: a versatile approach to tetrahydroquinolines, 2,3-dihydro-4-quinolones, and 4-quinolones.

Organic letters

Cheng D, Zhou J, Saiah E, Beaton G.
PMID: 12465900
Org Lett. 2002 Dec 12;4(25):4411-4. doi: 10.1021/ol020179d.

[reaction: see text] The first successful use of ketene dithioacetals as dienophiles in the aza-Diels-Alder reaction with N-arylimines is described. Among the ketene dithioacetals tested, 1,4-benzodithiafulvenes are most effective in assembling the tetrahydroquinoline core. Subsequent chemical manipulations provide a...

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Cheng D, Zhou J, Saiah E, et al. Ketene dithioacetals in the aza-Diels-Alder reaction with N-arylimines: a versatile approach to tetrahydroquinolines, 2,3-dihydro-4-quinolones, and 4-quinolones. Org Lett. 2002;4(25):4411-4doi: 10.1021/ol020179d.
Cheng, D., Zhou, J., Saiah, E., & Beaton, G. (2002). Ketene dithioacetals in the aza-Diels-Alder reaction with N-arylimines: a versatile approach to tetrahydroquinolines, 2,3-dihydro-4-quinolones, and 4-quinolones. Organic letters, 4(25), 4411-4. https://doi.org/10.1021/ol020179d
Cheng, Dai, et al. "Ketene dithioacetals in the aza-Diels-Alder reaction with N-arylimines: a versatile approach to tetrahydroquinolines, 2,3-dihydro-4-quinolones, and 4-quinolones." Organic letters vol. 4,25 (2002): 4411-4. doi: https://doi.org/10.1021/ol020179d
Cheng D, Zhou J, Saiah E, Beaton G. Ketene dithioacetals in the aza-Diels-Alder reaction with N-arylimines: a versatile approach to tetrahydroquinolines, 2,3-dihydro-4-quinolones, and 4-quinolones. Org Lett. 2002 Dec 12;4(25):4411-4. doi: 10.1021/ol020179d. PMID: 12465900.
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Essential Guide of Analysis Methods Applied to Silver Complexes with Antibacterial Quinolones.

Advanced pharmaceutical bulletin

Rusu A, Hancu G, Imre S.
PMID: 30023319
Adv Pharm Bull. 2018 Jun;8(2):181-189. doi: 10.15171/apb.2018.022. Epub 2018 Jun 19.

To describe the chemical structure and characterize physico-chemical properties of organometallic complexes it is necessary to use a complex set of analysis methods. Thus, this review has been compiled as a relevant guide which includes the most commonly used...

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Rusu A, Hancu G, Imre S. Essential Guide of Analysis Methods Applied to Silver Complexes with Antibacterial Quinolones. Adv Pharm Bull. 2018;8(2):181-189doi: 10.15171/apb.2018.022.
Rusu, A., Hancu, G., & Imre, S. (2018). Essential Guide of Analysis Methods Applied to Silver Complexes with Antibacterial Quinolones. Advanced pharmaceutical bulletin, 8(2), 181-189. https://doi.org/10.15171/apb.2018.022
Rusu, Aura, et al. "Essential Guide of Analysis Methods Applied to Silver Complexes with Antibacterial Quinolones." Advanced pharmaceutical bulletin vol. 8,2 (2018): 181-189. doi: https://doi.org/10.15171/apb.2018.022
Rusu A, Hancu G, Imre S. Essential Guide of Analysis Methods Applied to Silver Complexes with Antibacterial Quinolones. Adv Pharm Bull. 2018 Jun;8(2):181-189. doi: 10.15171/apb.2018.022. Epub 2018 Jun 19. PMID: 30023319; PMCID: PMC6046430.
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Showing 1 to 12 of 37 entries