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Synthesis of dihydroquinolinones via iridium-catalyzed cascade C-H amidation and intramolecular aza-Michael addition.

Chemical communications (Cambridge, England)

Pan C, Yang Z, Xiong H, Teng J, Wang Y, Yu JT.
PMID: 30676590
Chem Commun (Camb). 2019 Feb 07;55(13):1915-1918. doi: 10.1039/c8cc09751h.

An iridium-catalyzed annulation of chalcones with sulfonyl azides via cascade C-H amidation and intramolecular aza-Michael addition was developed, affording a variety of 2-aryl-2,3-dihydro-4-quinolones in moderate to good yields. This reaction features easy operation, readily available starting materials, and the...

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Pan C, Yang Z, Xiong H, et al. Synthesis of dihydroquinolinones via iridium-catalyzed cascade C-H amidation and intramolecular aza-Michael addition. Chem Commun (Camb). 2019;55(13):1915-1918doi: 10.1039/c8cc09751h.
Pan, C., Yang, Z., Xiong, H., Teng, J., Wang, Y., & Yu, J. T. (2019). Synthesis of dihydroquinolinones via iridium-catalyzed cascade C-H amidation and intramolecular aza-Michael addition. Chemical communications (Cambridge, England), 55(13), 1915-1918. https://doi.org/10.1039/c8cc09751h
Pan, Changduo, et al. "Synthesis of dihydroquinolinones via iridium-catalyzed cascade C-H amidation and intramolecular aza-Michael addition." Chemical communications (Cambridge, England) vol. 55,13 (2019): 1915-1918. doi: https://doi.org/10.1039/c8cc09751h
Pan C, Yang Z, Xiong H, Teng J, Wang Y, Yu JT. Synthesis of dihydroquinolinones via iridium-catalyzed cascade C-H amidation and intramolecular aza-Michael addition. Chem Commun (Camb). 2019 Feb 07;55(13):1915-1918. doi: 10.1039/c8cc09751h. PMID: 30676590.
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Norfloxacin, the first of a new class of fluoroquinolone antimicrobials, revisited.

International journal of antimicrobial agents

Gadebusch HH, Shungu DL.
PMID: 18611490
Int J Antimicrob Agents. 1991;1(1):3-28. doi: 10.1016/0924-8579(91)90019-a.

Norfloxacin is the first in a series of new 4-quinolones that have been introduced into medical practice for the treatment of bacterial infections. This totally synthetic compound is a broad spectrum, bactericidal agent that is much more potent than...

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Gadebusch HH, Shungu DL. Norfloxacin, the first of a new class of fluoroquinolone antimicrobials, revisited. Int J Antimicrob Agents. 1991;1(1):3-28doi: 10.1016/0924-8579(91)90019-a.
Gadebusch, H. H., & Shungu, D. L. (1991). Norfloxacin, the first of a new class of fluoroquinolone antimicrobials, revisited. International journal of antimicrobial agents, 1(1), 3-28. https://doi.org/10.1016/0924-8579(91)90019-a
Gadebusch, H H, and Shungu, D L. "Norfloxacin, the first of a new class of fluoroquinolone antimicrobials, revisited." International journal of antimicrobial agents vol. 1,1 (1991): 3-28. doi: https://doi.org/10.1016/0924-8579(91)90019-a
Gadebusch HH, Shungu DL. Norfloxacin, the first of a new class of fluoroquinolone antimicrobials, revisited. Int J Antimicrob Agents. 1991;1(1):3-28. doi: 10.1016/0924-8579(91)90019-a. PMID: 18611490.
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Switchable Access to 3-Carboxylate-4-quinolones and 1-Vinyl-3-carboxylate-4-quinolones via Oxidative Cyclization of Isatins and Alkynes.

Organic letters

Jiang SF, Xu C, Zhou ZW, Zhang Q, Wen XH, Jia FC, Wu AX.
PMID: 29953242
Org Lett. 2018 Jul 20;20(14):4231-4234. doi: 10.1021/acs.orglett.8b01645. Epub 2018 Jun 28.

An efficient transition-metal-free oxidative cyclization reaction using isatins and alkynes for the facile synthesis of structurally diverse 4-quinolones has been developed. Intriguingly, switchable access to substituted 3-carboxylate-4-quinolones and 1-vinyl-3-carboxylate-4-quinolones could be achieved by choosing a different base in the...

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Jiang SF, Xu C, Zhou ZW, et al. Switchable Access to 3-Carboxylate-4-quinolones and 1-Vinyl-3-carboxylate-4-quinolones via Oxidative Cyclization of Isatins and Alkynes. Org Lett. 2018;20(14):4231-4234doi: 10.1021/acs.orglett.8b01645.
Jiang, S. F., Xu, C., Zhou, Z. W., Zhang, Q., Wen, X. H., Jia, F. C., & Wu, A. X. (2018). Switchable Access to 3-Carboxylate-4-quinolones and 1-Vinyl-3-carboxylate-4-quinolones via Oxidative Cyclization of Isatins and Alkynes. Organic letters, 20(14), 4231-4234. https://doi.org/10.1021/acs.orglett.8b01645
Jiang, Shi-Fen, et al. "Switchable Access to 3-Carboxylate-4-quinolones and 1-Vinyl-3-carboxylate-4-quinolones via Oxidative Cyclization of Isatins and Alkynes." Organic letters vol. 20,14 (2018): 4231-4234. doi: https://doi.org/10.1021/acs.orglett.8b01645
Jiang SF, Xu C, Zhou ZW, Zhang Q, Wen XH, Jia FC, Wu AX. Switchable Access to 3-Carboxylate-4-quinolones and 1-Vinyl-3-carboxylate-4-quinolones via Oxidative Cyclization of Isatins and Alkynes. Org Lett. 2018 Jul 20;20(14):4231-4234. doi: 10.1021/acs.orglett.8b01645. Epub 2018 Jun 28. PMID: 29953242.
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A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives.

The Journal of organic chemistry

Xie C, Yang D, Wang X, Ma C.
PMID: 33146531
J Org Chem. 2020 Dec 04;85(23):14937-14944. doi: 10.1021/acs.joc.0c01662. Epub 2020 Nov 04.

A novel transition-metal-free cascade reaction to synthesize 4-quinolone derivatives has been demonstrated. Michael addition and Truce-Smiles rearrangement are included in this protocol, providing a broad scope of 4-quinolones in moderate-to-excellent yields. This work serves as an example of the...

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Xie C, Yang D, Wang X, et al. A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives. J Org Chem. 2020;85(23):14937-14944doi: 10.1021/acs.joc.0c01662.
Xie, C., Yang, D., Wang, X., & Ma, C. (2020). A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives. The Journal of organic chemistry, 85(23), 14937-14944. https://doi.org/10.1021/acs.joc.0c01662
Xie, Caixia, et al. "A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives." The Journal of organic chemistry vol. 85,23 (2020): 14937-14944. doi: https://doi.org/10.1021/acs.joc.0c01662
Xie C, Yang D, Wang X, Ma C. A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives. J Org Chem. 2020 Dec 04;85(23):14937-14944. doi: 10.1021/acs.joc.0c01662. Epub 2020 Nov 04. PMID: 33146531.
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KHCO.

Chemistry, an Asian journal

Ma H, Zhou X, Wei D, Cao J, Shi C, Fan Y, Huang G.
PMID: 27582251
Chem Asian J. 2016 Oct 20;11(20):2829-2833. doi: 10.1002/asia.201600901. Epub 2016 Sep 15.

A novel and convenient one-pot route for the synthesis of 3-benzyl-2-phenylquinolin-4(1 H)-ones has been developed under transition-metal-free conditions. This new strategy features high yield and good functional group tolerance. In addition, a proposed mechanism has been confirmed for this...

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Ma H, Zhou X, Wei D, et al. KHCO. Chem Asian J. 2016;11(20):2829-2833doi: 10.1002/asia.201600901.
Ma, H., Zhou, X., Wei, D., Cao, J., Shi, C., Fan, Y., & Huang, G. (2016). KHCO. Chemistry, an Asian journal, 11(20), 2829-2833. https://doi.org/10.1002/asia.201600901
Ma, Haojie, et al. "KHCO." Chemistry, an Asian journal vol. 11,20 (2016): 2829-2833. doi: https://doi.org/10.1002/asia.201600901
Ma H, Zhou X, Wei D, Cao J, Shi C, Fan Y, Huang G. KHCO. Chem Asian J. 2016 Oct 20;11(20):2829-2833. doi: 10.1002/asia.201600901. Epub 2016 Sep 15. PMID: 27582251.
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Programmed Multiple C-H Bond Functionalization of the Privileged 4-hydroxyquinoline Template.

Chemistry (Weinheim an der Bergstrasse, Germany)

Ronzon Q, Zhang W, Casaretto N, Mouray E, Florent I, Nay B.
PMID: 33848033
Chemistry. 2021 May 17;27(28):7764-7772. doi: 10.1002/chem.202100929. Epub 2021 Apr 30.

The introduction of substituents on bare heterocyclic scaffolds can selectively be achieved by directed C-H functionalization. However, such methods have only occasionally been used, in an iterative manner, to decorate various positions of a medicinal scaffold to build chemical...

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Ronzon Q, Zhang W, Casaretto N, et al. Programmed Multiple C-H Bond Functionalization of the Privileged 4-hydroxyquinoline Template. Chemistry. 2021;27(28):7764-7772doi: 10.1002/chem.202100929.
Ronzon, Q., Zhang, W., Casaretto, N., Mouray, E., Florent, I., & Nay, B. (2021). Programmed Multiple C-H Bond Functionalization of the Privileged 4-hydroxyquinoline Template. Chemistry (Weinheim an der Bergstrasse, Germany), 27(28), 7764-7772. https://doi.org/10.1002/chem.202100929
Ronzon, Quentin, et al. "Programmed Multiple C-H Bond Functionalization of the Privileged 4-hydroxyquinoline Template." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 27,28 (2021): 7764-7772. doi: https://doi.org/10.1002/chem.202100929
Ronzon Q, Zhang W, Casaretto N, Mouray E, Florent I, Nay B. Programmed Multiple C-H Bond Functionalization of the Privileged 4-hydroxyquinoline Template. Chemistry. 2021 May 17;27(28):7764-7772. doi: 10.1002/chem.202100929. Epub 2021 Apr 30. PMID: 33848033.
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Novel detection of specific bacterial quorum sensing molecules in saliva: Potential non-invasive biomarkers for pulmonary Pseudomonas aeruginosa in cystic fibrosis.

Journal of cystic fibrosis : official journal of the European Cystic Fibrosis Society

Webb K, Cámara M, Zain NMM, Halliday N, Bruce KD, Nash EF, Whitehouse JL, Knox A, Forrester D, Smyth AR, Williams P, Fogarty A, Barr HL.
PMID: 34518117
J Cyst Fibros. 2021 Sep 10; doi: 10.1016/j.jcf.2021.08.030. Epub 2021 Sep 10.

Pseudomonas aeruginosa produces specific signalling molecules, 2-alkyl-4-quinolones (AQs) that are detectable in the sputum of adults with cystic fibrosis (CF) and who have pulmonary infection with this opportunistic pathogen. This study aimed to determine whether AQs could be detected...

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Webb K, Cámara M, Zain NMM, et al. Novel detection of specific bacterial quorum sensing molecules in saliva: Potential non-invasive biomarkers for pulmonary Pseudomonas aeruginosa in cystic fibrosis. J Cyst Fibros. 2021;doi: 10.1016/j.jcf.2021.08.030.
Webb, K., Cámara, M., Zain, N. M. M., Halliday, N., Bruce, K. D., Nash, E. F., Whitehouse, J. L., Knox, A., Forrester, D., Smyth, A. R., Williams, P., Fogarty, A., & Barr, H. L. (2021). Novel detection of specific bacterial quorum sensing molecules in saliva: Potential non-invasive biomarkers for pulmonary Pseudomonas aeruginosa in cystic fibrosis. Journal of cystic fibrosis : official journal of the European Cystic Fibrosis Society, . https://doi.org/10.1016/j.jcf.2021.08.030
Webb, Karmel, et al. "Novel detection of specific bacterial quorum sensing molecules in saliva: Potential non-invasive biomarkers for pulmonary Pseudomonas aeruginosa in cystic fibrosis." Journal of cystic fibrosis : official journal of the European Cystic Fibrosis Society vol. (2021). doi: https://doi.org/10.1016/j.jcf.2021.08.030
Webb K, Cámara M, Zain NMM, Halliday N, Bruce KD, Nash EF, Whitehouse JL, Knox A, Forrester D, Smyth AR, Williams P, Fogarty A, Barr HL. Novel detection of specific bacterial quorum sensing molecules in saliva: Potential non-invasive biomarkers for pulmonary Pseudomonas aeruginosa in cystic fibrosis. J Cyst Fibros. 2021 Sep 10; doi: 10.1016/j.jcf.2021.08.030. Epub 2021 Sep 10. PMID: 34518117.
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Kinetic resolution of 2,3-dihydro-2-substituted 4-quinolones by palladium-catalyzed asymmetric allylic alkylation.

Journal of the American Chemical Society

Lei BL, Ding CH, Yang XF, Wan XL, Hou XL.
PMID: 19994886
J Am Chem Soc. 2009 Dec 30;131(51):18250-1. doi: 10.1021/ja9082717.

The kinetic resolution of a carbon nucleophile is realized for the first time via Pd-catalyzed asymmetric allylic alkylation with "unstabilized" ketone enolates as the nucleophile, providing both allylated 2,3-disubstituted 2,3-dihydro-4-quinolones and recovered substrates in high yields and high ee...

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Lei BL, Ding CH, Yang XF, et al. Kinetic resolution of 2,3-dihydro-2-substituted 4-quinolones by palladium-catalyzed asymmetric allylic alkylation. J Am Chem Soc. 2009;131(51):18250-1doi: 10.1021/ja9082717.
Lei, B. L., Ding, C. H., Yang, X. F., Wan, X. L., & Hou, X. L. (2009). Kinetic resolution of 2,3-dihydro-2-substituted 4-quinolones by palladium-catalyzed asymmetric allylic alkylation. Journal of the American Chemical Society, 131(51), 18250-1. https://doi.org/10.1021/ja9082717
Lei, Bai-Lin, et al. "Kinetic resolution of 2,3-dihydro-2-substituted 4-quinolones by palladium-catalyzed asymmetric allylic alkylation." Journal of the American Chemical Society vol. 131,51 (2009): 18250-1. doi: https://doi.org/10.1021/ja9082717
Lei BL, Ding CH, Yang XF, Wan XL, Hou XL. Kinetic resolution of 2,3-dihydro-2-substituted 4-quinolones by palladium-catalyzed asymmetric allylic alkylation. J Am Chem Soc. 2009 Dec 30;131(51):18250-1. doi: 10.1021/ja9082717. PMID: 19994886.
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Cobalt(III)- and Rhodium(III)-Catalyzed C-H Amidation and Synthesis of 4-Quinolones: C-H Activation Assisted by Weakly Coordinating and Functionalizable Enaminone.

Organic letters

Wang F, Jin L, Kong L, Li X.
PMID: 28358202
Org Lett. 2017 Apr 07;19(7):1812-1815. doi: 10.1021/acs.orglett.7b00583. Epub 2017 Mar 30.

Cobalt(III) and rhodium(III) catalysts exhibited complementary scope in C-H amidation of aryl enaminones. The amidation reactions proceeded with broad scope under the assistance of a weakly coordinating and bifunctional enaminone directing group. The electrophilicity of the enaminone group can...

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Wang F, Jin L, Kong L, et al. Cobalt(III)- and Rhodium(III)-Catalyzed C-H Amidation and Synthesis of 4-Quinolones: C-H Activation Assisted by Weakly Coordinating and Functionalizable Enaminone. Org Lett. 2017;19(7):1812-1815doi: 10.1021/acs.orglett.7b00583.
Wang, F., Jin, L., Kong, L., & Li, X. (2017). Cobalt(III)- and Rhodium(III)-Catalyzed C-H Amidation and Synthesis of 4-Quinolones: C-H Activation Assisted by Weakly Coordinating and Functionalizable Enaminone. Organic letters, 19(7), 1812-1815. https://doi.org/10.1021/acs.orglett.7b00583
Wang, Fen, et al. "Cobalt(III)- and Rhodium(III)-Catalyzed C-H Amidation and Synthesis of 4-Quinolones: C-H Activation Assisted by Weakly Coordinating and Functionalizable Enaminone." Organic letters vol. 19,7 (2017): 1812-1815. doi: https://doi.org/10.1021/acs.orglett.7b00583
Wang F, Jin L, Kong L, Li X. Cobalt(III)- and Rhodium(III)-Catalyzed C-H Amidation and Synthesis of 4-Quinolones: C-H Activation Assisted by Weakly Coordinating and Functionalizable Enaminone. Org Lett. 2017 Apr 07;19(7):1812-1815. doi: 10.1021/acs.orglett.7b00583. Epub 2017 Mar 30. PMID: 28358202.
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Using differential ion mobility spectrometry to perform class-specific ion-molecule reactions of 4-quinolones with selected chemical reagents.

Analytical and bioanalytical chemistry

Schorr P, Volmer DA.
PMID: 30972473
Anal Bioanal Chem. 2019 Sep;411(24):6247-6253. doi: 10.1007/s00216-019-01789-z. Epub 2019 Apr 10.

Gas phase ion/molecule reactions are often used in analytical applications to support the analysis of isomers or to identify specific functional groups of organic molecules. Until now, deliberate chemical reactions have not been performed in differential ion mobility spectrometry...

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Schorr P, Volmer DA. Using differential ion mobility spectrometry to perform class-specific ion-molecule reactions of 4-quinolones with selected chemical reagents. Anal Bioanal Chem. 2019;411(24):6247-6253doi: 10.1007/s00216-019-01789-z.
Schorr, P., & Volmer, D. A. (2019). Using differential ion mobility spectrometry to perform class-specific ion-molecule reactions of 4-quinolones with selected chemical reagents. Analytical and bioanalytical chemistry, 411(24), 6247-6253. https://doi.org/10.1007/s00216-019-01789-z
Schorr, Pascal, and Volmer, Dietrich A. "Using differential ion mobility spectrometry to perform class-specific ion-molecule reactions of 4-quinolones with selected chemical reagents." Analytical and bioanalytical chemistry vol. 411,24 (2019): 6247-6253. doi: https://doi.org/10.1007/s00216-019-01789-z
Schorr P, Volmer DA. Using differential ion mobility spectrometry to perform class-specific ion-molecule reactions of 4-quinolones with selected chemical reagents. Anal Bioanal Chem. 2019 Sep;411(24):6247-6253. doi: 10.1007/s00216-019-01789-z. Epub 2019 Apr 10. PMID: 30972473.
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Direct Synthesis of 4-Quinolones via Copper-Catalyzed Intermolecular Cyclization of Anilines and Alkynes.

Organic letters

Xu X, Zhang X.
PMID: 28880567
Org Lett. 2017 Sep 15;19(18):4984-4987. doi: 10.1021/acs.orglett.7b02495. Epub 2017 Sep 07.

A unique and direct approach for constructing 4-quinolones from simple and readily available anilines and alkynes is described. Under the optimal conditions, both N-alkyl- and N-aryl-substituted anilines can be successfully transformed into the corresponding 4-quinolones. This reaction is characterized...

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Xu X, Zhang X. Direct Synthesis of 4-Quinolones via Copper-Catalyzed Intermolecular Cyclization of Anilines and Alkynes. Org Lett. 2017;19(18):4984-4987doi: 10.1021/acs.orglett.7b02495.
Xu, X., & Zhang, X. (2017). Direct Synthesis of 4-Quinolones via Copper-Catalyzed Intermolecular Cyclization of Anilines and Alkynes. Organic letters, 19(18), 4984-4987. https://doi.org/10.1021/acs.orglett.7b02495
Xu, Xuefeng, and Zhang, Xu. "Direct Synthesis of 4-Quinolones via Copper-Catalyzed Intermolecular Cyclization of Anilines and Alkynes." Organic letters vol. 19,18 (2017): 4984-4987. doi: https://doi.org/10.1021/acs.orglett.7b02495
Xu X, Zhang X. Direct Synthesis of 4-Quinolones via Copper-Catalyzed Intermolecular Cyclization of Anilines and Alkynes. Org Lett. 2017 Sep 15;19(18):4984-4987. doi: 10.1021/acs.orglett.7b02495. Epub 2017 Sep 07. PMID: 28880567.
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The incidences of resistance to cephalosporins and fluorinated 4-quinolones in similar strains isolated in Glasgow and Edinburgh.

International journal of antimicrobial agents

Paton RH, Thomson CJ, Hood J, Dallas S, Miles RS, Amyes SG.
PMID: 18611527
Int J Antimicrob Agents. 1993 Feb;2(2):89-96. doi: 10.1016/0924-8579(93)90046-8.

Bacterial sensitivity to cefuroxime, ceftazidime, cefotaxime, ciprofloxacin and ofloxacin was determined for 1386 urinary and bacteraemia isolates from Glasgow and Edinburgh to detemine the impact of these antibacterials on the development of resistance. The MIC(50) and MIC(90) values were...

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Paton RH, Thomson CJ, Hood J, et al. The incidences of resistance to cephalosporins and fluorinated 4-quinolones in similar strains isolated in Glasgow and Edinburgh. Int J Antimicrob Agents. 1993;2(2):89-96doi: 10.1016/0924-8579(93)90046-8.
Paton, R. H., Thomson, C. J., Hood, J., Dallas, S., Miles, R. S., & Amyes, S. G. (1993). The incidences of resistance to cephalosporins and fluorinated 4-quinolones in similar strains isolated in Glasgow and Edinburgh. International journal of antimicrobial agents, 2(2), 89-96. https://doi.org/10.1016/0924-8579(93)90046-8
Paton, R H, et al. "The incidences of resistance to cephalosporins and fluorinated 4-quinolones in similar strains isolated in Glasgow and Edinburgh." International journal of antimicrobial agents vol. 2,2 (1993): 89-96. doi: https://doi.org/10.1016/0924-8579(93)90046-8
Paton RH, Thomson CJ, Hood J, Dallas S, Miles RS, Amyes SG. The incidences of resistance to cephalosporins and fluorinated 4-quinolones in similar strains isolated in Glasgow and Edinburgh. Int J Antimicrob Agents. 1993 Feb;2(2):89-96. doi: 10.1016/0924-8579(93)90046-8. PMID: 18611527.
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Showing 13 to 24 of 37 entries