Copper(I)-catalyzed [3 + 2] cycloaddition of 3-azidoquinoline-2,4(1H,3H)-diones with terminal alkynes

Kafka, Stanislav (author), Hauke, Sylvia (author), Salčinović, Arjana (author), Soidinsalo, Otto (author), Urankar, Damijana (author), Košmrlj, Janez (author)

3-Azidoquinoline-2,4(1H,3H)-diones 1, which are readily available from 4-hydroxyquinolin-2(1H)-ones 4 via 3-chloroquinoline-2,4(1H,3H)-diones 5, afford, in copper(I)-catalyzed [3 + 2] cycloaddition reaction with terminal acetylenes, 1,4-disubstituted 1,2,3-triazoles 3 in moderate to excellent yields. The structures of compounds 3 were confirmed by $^1$H and $^{13}$C-NMR spectroscopy, combustion analyses and mass spectrometry.

• Language: English
• Keywords: cycloaddition, azides, quinoline-2, 4(1H, 3H)-diones, terminal alkynes, 1, 2, 3-triazoles
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2011
• Number of pages: Str. 4070-4081
• Numbering: Vol. 16, iss. 5
• PID: 20.500.12556/RUL-129624
• UDC: 547.831.057:547.79:546.561
• ISSN on article: 1420-3049
• DOI: 10.3390/molecules16054070
• COBISS.SI-ID: 35032581
• Publication date in RUL: 06.09.2021

Record is a part of a journal

• Title: Molecules
• Shortened title: Molecules
• Publisher: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

Licences

• License: CC BY 3.0, Creative Commons Attribution 3.0 Unported
• Link: https://creativecommons.org/licenses/by/3.0/deed.en
• Description: You are free to reproduce and redistribute the material in any medium or format. You are free to remix, transform, and build upon the material for any purpose, even commercially. You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not apply legal terms or technological measures that legally restrict others from doing anything the license permits.
• Licensing start date: 18.05.2011

Secondary language

• Language: Slovenian
• Keywords: organska kemija, sinteza, organske sinteze, kataliza, cikloadicija, heterociklične spojine, heterociklični sistemi, heterocikli, derivati kinolona, kinoloni, azidi, azidokinoloni, terminalni alkini, triazoli, baker