Synthesis of 6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazoles by azomethine imine-alkyne cycloadditions using immobilized Cu(II)-catalysts

Štanfel, Urša (avtor), Slapšak, Dejan (avtor), Grošelj, Uroš (avtor), Požgan, Franc (avtor), Štefane, Bogdan (avtor), Svete, Jurij (avtor)

A series of 12 silica gel-bound enaminones and their Cu(II) complexes were prepared and tested for their suitability as heterogeneous catalysts in azomethine imine-alkyne cycloadditions (CuAIAC). Immobilized Cu(II)–enaminone complexes showed promising catalytic activity in the CuAIAC reaction, but these new catalysts suffered from poor reusability. This was not due to the decoordination of copper ions, as the use of enaminone ligands with additional complexation sites resulted in negligible improvement. On the other hand, reusability was improved by the use of 4-aminobenzoic acid linker, attached to 3-aminopropyl silica gel via an amide bond to the enaminone over the more hydrolytically stable N-arylenamine C-N bond. The study showed that silica gelbound Cu(II)–enaminone complexes are readily available and suitable heterogeneous catalysts for the synthesis of 6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazoles.

• Jezik: Angleški jezik
• Ključne besede: 1, 3-dipolar cycloadditions, 2, 3-dihydropyrazolo[1, 2-a]pyrazoles, copper-catalyzed azomethine imine-alkyne cycloaddition (CuAIAC), azomethine imines, ynones
• 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: 2021
• Št. strani: 18 str.
• Številčenje: Vol. 26, iss. 2, art. 400
• PID: 20.500.12556/RUL-134926
• UDK: 547.78
• ISSN pri članku: 1420-3049
• DOI: 10.3390/molecules26020400
• COBISS.SI-ID: 46951171
• Datum objave v RUL: 11.02.2022

Gradivo je del revije

• Naslov: Molecules
• Skrajšan naslov: Molecules
• Založnik: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

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.
• Začetek licenciranja: 13.01.2021

Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: 1, 3-dipolarne cikloadicije, 2, 3-dihidropirazolo[1, 2-a]pirazoli, z bakrom katalizirane cikloadicije, CuAIAC, azometin imini, inoni, alkini

Projekti

• Financer: ARRS - Agencija za raziskovalno dejavnost Republike Slovenije
• Številka projekta: P1-0179
• Naslov: Napredna organska sinteza in kataliza