Tags

Type your tag names separated by a space and hit enter

Gold(iii)-catalyzed azide-yne cyclization/O-H insertion cascade reaction for the expeditious construction of 3-alkoxy-4-quinolinone frameworks.
Org Biomol Chem. 2020 05 27; 18(20):3888-3892.OB

Abstract

A gold-catalyzed 6-endo-dig azide-yne cyclization/O-H insertion cascade reaction of azide-tethered alkynes with alcohols has been developed, and it provides an expeditious access to 3-alkoxy-4-quinoline derivatives in good to high yields under mild and neutral reaction conditions with broad substrate generality. The utility of this method is emphasized by a scalable experiment and concise total synthesis of a bioactive natural product Leiokinine A, and other bioactive quinoline analogs.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Huang J
Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China. zhangyq65@mail.sysu.edu.cn xuxinfang@mail.sysu.edu.cn.
Su H
College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.
Bao M
Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China. zhangyq65@mail.sysu.edu.cn xuxinfang@mail.sysu.edu.cn.
Qiu L
College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.
Zhang Y
Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China. zhangyq65@mail.sysu.edu.cn xuxinfang@mail.sysu.edu.cn.
Xu X
Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China. zhangyq65@mail.sysu.edu.cn xuxinfang@mail.sysu.edu.cn and College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

32373897

Citation

Huang, Jingjing, et al. "Gold(iii)-catalyzed Azide-yne cyclization/O-H Insertion Cascade Reaction for the Expeditious Construction of 3-alkoxy-4-quinolinone Frameworks." Organic & Biomolecular Chemistry, vol. 18, no. 20, 2020, pp. 3888-3892.
Huang J, Su H, Bao M, et al. Gold(iii)-catalyzed azide-yne cyclization/O-H insertion cascade reaction for the expeditious construction of 3-alkoxy-4-quinolinone frameworks. Org Biomol Chem. 2020;18(20):3888-3892.
Huang, J., Su, H., Bao, M., Qiu, L., Zhang, Y., & Xu, X. (2020). Gold(iii)-catalyzed azide-yne cyclization/O-H insertion cascade reaction for the expeditious construction of 3-alkoxy-4-quinolinone frameworks. Organic & Biomolecular Chemistry, 18(20), 3888-3892. https://doi.org/10.1039/d0ob00745e
Huang J, et al. Gold(iii)-catalyzed Azide-yne cyclization/O-H Insertion Cascade Reaction for the Expeditious Construction of 3-alkoxy-4-quinolinone Frameworks. Org Biomol Chem. 2020 05 27;18(20):3888-3892. PubMed PMID: 32373897.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Gold(iii)-catalyzed azide-yne cyclization/O-H insertion cascade reaction for the expeditious construction of 3-alkoxy-4-quinolinone frameworks. AU - Huang,Jingjing, AU - Su,Han, AU - Bao,Ming, AU - Qiu,Lihua, AU - Zhang,Yuanqing, AU - Xu,Xinfang, PY - 2020/5/7/pubmed PY - 2020/5/7/medline PY - 2020/5/7/entrez SP - 3888 EP - 3892 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 18 IS - 20 N2 - A gold-catalyzed 6-endo-dig azide-yne cyclization/O-H insertion cascade reaction of azide-tethered alkynes with alcohols has been developed, and it provides an expeditious access to 3-alkoxy-4-quinoline derivatives in good to high yields under mild and neutral reaction conditions with broad substrate generality. The utility of this method is emphasized by a scalable experiment and concise total synthesis of a bioactive natural product Leiokinine A, and other bioactive quinoline analogs. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/32373897/Gold_iii__catalyzed_azide_yne_cyclization/O_H_insertion_cascade_reaction_for_the_expeditious_construction_of_3_alkoxy_4_quinolinone_frameworks_ DB - PRIME DP - Unbound Medicine ER -