Synthesis, structure, and optical properties of 3-(1H-1,2,3-triazol-1-yl)-substituted 4H-pyrido[1,2–a]pyrimidin-4-ones and 4H-quinolizin-4-ones

Humar, Tadej (avtor), Ciber, Luka (avtor), Grošelj, Uroš (avtor), Petek, Nejc (avtor), Štefane, Bogdan (avtor), Svete, Jurij (avtor)

Copper-catalyzed cycloadditions of terminal alkynes to 3-azido-4H-pyrido[1,2–a]pyrimidin-4-one and 3-azido-1-cyano-4H-quinolizin-4-one, prepared in four steps from methyl 2-benzoylamino-3-(dimethylamino)propenoate, yielded the corresponding 3-(1H-1,2,3-triazol-1-yl)-substituted 4H-pyrido[1,2–a]pyrimidin-4-ones and 4H-quinolizin-4-ones in 44–90 % isolated yields. The structures of the cycloadducts were determined by $^1$H NMR, $^{13}$C NMR, and 2D NMR techniques (COSY, HSQC, HMBC). The optical properties of the luminescent intermediates and final products were determined. In methanol, the compounds showed absorption at 350–400 nm, emission at 411–526 nm, and quantum yields of ∼5 × 10$^{−2}$. Optical properties depended on the heterocyclic core (pyrido[1,2–a]pyrimidinone or quinolizinone), while the effect of substituents on optical properties was weak.

• Jezik: Angleški jezik
• Ključne besede: quinolizines, azaquinolizines, alkynes, copper-catalyzed azide-alkyne cycloadditions, bioconjugation, fluorescent labelling
• Vrsta gradiva: Članek v reviji
• Tipologija: 1.01 - Izvirni znanstveni članek
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Status publikacije: Objavljeno
• Različica publikacije: Objavljena publikacija
• Leto izida: 2026
• Št. strani: 13 str.
• Številčenje: Vol. 247, art. 113434
• PID: 20.500.12556/RUL-176451
• UDK: 547.83
• ISSN pri članku: 0143-7208
• DOI: 10.1016/j.dyepig.2025.113434
• COBISS.SI-ID: 259137283
• Datum objave v RUL: 01.12.2025

Gradivo je del revije

• Naslov: Dyes and pigments
• Skrajšan naslov: Dyes pigm.
• Založnik: Elsevier
• ISSN: 0143-7208
• COBISS.SI-ID: 25357056

Licence

• Licenca: CC BY 4.0, Creative Commons Priznanje avtorstva 4.0 Mednarodna
• Povezava: http://creativecommons.org/licenses/by/4.0/deed.sl
• Opis: To je standardna licenca Creative Commons, ki daje uporabnikom največ možnosti za nadaljnjo uporabo dela, pri čemer morajo navesti avtorja.

Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: kinolizini, azakinolizini, alkini, z bakrom katalizirane azid-alkin cikloadicije, biokonjugacija, fluorescenčno označevanje