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

Abstract

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.

Keywords

1,3-dipolarne cikloadicije;2,3-dihidropirazolo[1,2-a]pirazoli;z bakrom katalizirane cikloadicije;CuAIAC;azometin imini;inoni;alkini;1,3-dipolar cycloadditions;2,3-dihydropyrazolo[1,2-a]pyrazoles;copper-catalyzed azomethine imine-alkyne cycloaddition;azomethine imines;ynones;

Data

Language: English
Year of publishing:
Typology: 1.01 - Original Scientific Article
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
UDC: 547.78
COBISS: 46951171 Link will open in a new window
ISSN: 1420-3049
Views: 179
Downloads: 60
Average score: 0 (0 votes)
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Other data

Secondary language: Slovenian
Secondary keywords: 1;3-dipolarne cikloadicije;2;3-dihidropirazolo[1;2-a]pirazoli;z bakrom katalizirane cikloadicije;CuAIAC;azometin imini;inoni;alkini;
Type (COBISS): Article
Pages: str. 1-18
Volume: ǂVol. ǂ26
Issue: ǂiss. ǂ2
Chronology: Jan. 2021
DOI: 10.3390/molecules26020400
ID: 14503996