Cascade C=O/C=C/C-N bond formation

• Verfasst von: Zhang, Bing [VerfasserIn]
• Verfasst von: Huang, Long [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: Cascade C=O/C=C/C-N bond formation
• Titelzusatz: metal-free reactions of 1,4-diynes and 1-En-4-yn-3-ones with isoquinoline and quinoline N-oxides
• Verf.angabe: Bing Zhang, Long Huang, Shiwei Yin, Xuetong Li, Tao Xu, Biyang Zhuang, Tao Wang, Zunting Zhang, A. Stephen K. Hashmi
• Umfang: 4 S.
• Fussnoten: Gesehen am 23.11.2017
• Titel Quelle: Enthalten in: Organic letters
• Jahr Quelle: 2017
• Band/Heft Quelle: 19(2017), 16, S. 4327-4330
• ISSN Quelle: 1523-7052
• DOI: doi:10.1021/acs.orglett.7b01996
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1565643305

Abstract

The metal-free reactions of 1,4-diynes and 1-en-4-yn-3-ones with isoquinoline and quinoline N-oxides are developed, resulting in the formation of 3,4-dihydro-2H-pyrido[2,1-a]isoquinolines and 2,3-dihydro-1H-pyrido[1,2-a]quinolines via cascade C═O/C═C/C-N bond formation. It is the first report in which in the alkyne oxidation by N-oxides both the oxygen atom of N-oxides and the nitrogen atom are involved in a second C-heteroatom bond formation. The reactions showed a broad substrate scope and functional group tolerance. Furthermore, the products were found to display green-blue fluorescence in DMSO with fluorescence quantum yields up to 0.59.