Solvent-free copper-catalyzed click chemistry for the synthesis of novel N-heterocyclic hybrids based on quinolone 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 (2017) Solvent-free copper-catalyzed click chemistry for the synthesis of novel N-heterocyclic hybrids based on quinolone and 1, 2, 3-triazole. Beilstein Journal of Organic Chemistry, 13 (13). pp. 2352-2363. ISSN 1860-5397

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Official URL: http://dx.doi.org/10.3762/bjoc.13.232

Abstract

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.

Item Type:

Article

Uncontrolled Keywords:

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

Subjects:

NATURAL SCIENCES > Chemistry

Divisions:

Division of Physical Chemistry

Projects:

Project title	Project leader	Project code	Project type
Mehaniokemijska reaktivnost pod kontroliranim uvjetima temperature i atmosfere za čišću sintezu funkcionalnih materijala-MECHANOCONTROL	Krunoslav Užarević	UIP-2014-09-4744	HRZZ
Karakterizacija niskotemperaturne molekulske dinamike sustava s neuređenom rešetkom metodom ESR-DESiRe	Marina Ilakovac Kveder	IP-2013-11-1108	HRZZ
SINTEZA I CITOSTATSKA ISPITIVANJA BIBLIOTEKE NOVIH DUŠIKOVIH HETEROCIKLA-SCIENcENTRY	Silvana Raić-Malić	IP-2013-11-5596	HRZZ