Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

Tireli, Martina; Maračić, Silvija; Lukin, Stipe; Juribašić Kulcsar, Marina; Žilić, Dijana; Cetina, Mario; Halasz, Ivan; Raić-Malić, Silvana; Užarević, Krunoslav

doi:10.3762/bjoc.13.232

Pregled bibliografske jedinice broj: 896561

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

Tireli, Martina; Maračić, Silvija; Lukin, Stipe; Juribašić Kulcsar, Marina; Žilić, Dijana; Cetina, Mario; Halasz, Ivan; Raić-Malić, Silvana; Užarević, Krunoslav

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole // Beilstein journal of organic chemistry, 13 (2017), 2352-2363 doi:10.3762/bjoc.13.232 (međunarodna recenzija, članak, znanstveni)

CROSBI ID: 896561 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

Autori
Tireli, Martina ; Maračić, Silvija ; Lukin, Stipe ; Juribašić Kulcsar, Marina ; Žilić, Dijana ; Cetina, Mario ; Halasz, Ivan ; Raić-Malić, Silvana ; Užarević, Krunoslav

Izvornik
Beilstein journal of organic chemistry (1860-5397) 13 (2017); 2352-2363

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
quinolone ; click chemistry ; mechanochemistry ; Raman monitoring ; Electron spin resonance (ESR) spectroscopy

Sažetak
Copper-catalyzed mechanochemical click reactions have been successfully implemented to provide novel 6-phenyl-2- (trifluoromethyl)quinolones with phenyl-1, 2, 3- triazole moiety at O-4 of quinolone core. Milling procedures utilizing CuI and brass milling balls proved to be more efficient than one using Cu(OAc)2, as a copper source. While solvent-free milling methods were unaffected by the presence of the p-substituted azides, solvent-based conventional methods were strongly dependent on electronic structure of azides. In situ Raman monitoring of the milling processes using the Cu(0) catalysts in form of brass milling media enabled direct insight into the reaction pathway of mechanochemical CuAAC reactions indicating that the catalysis is most likely conducted on the surface of milling balls.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA

Projekti:
HRZZ-UIP-2014-09-4744 - Mehanokemijska reaktivnost pod kontroliranim uvjetima temperature i atmosfere za čišću sintezu funkcionalnih materijala (MECHANOCONTROL) (Užarević, Krunoslav, HRZZ - 2014-09) ( CroRIS)
IP-2013-11-1108 - Karakterizacija niskotemperaturne molekulske dinamike sustava s neuređenom rešetkom metodom ESR (DESiRe) (Ilakovac Kveder, Marina, HRZZ - 2013-11) ( CroRIS)
HRZZ-IP-2013-11-5596 - Sinteza i citostatska ispitivanja biblioteke novih dušikovih heterocikla (SCIENcENTRY) (Raić-Malić, Silvana, HRZZ - 2013-11) ( CroRIS)

Ustanove:
Institut "Ruđer Bošković", Zagreb,
Tekstilno-tehnološki fakultet, Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Profili:

Martina Tireli (autor)