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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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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 titleProject leaderProject codeProject type
Mehaniokemijska reaktivnost pod kontroliranim uvjetima temperature i atmosfere za čišću sintezu funkcionalnih materijala-MECHANOCONTROLKrunoslav UžarevićUIP-2014-09-4744HRZZ
Karakterizacija niskotemperaturne molekulske dinamike sustava s neuređenom rešetkom metodom ESR-DESiReMarina Ilakovac KvederIP-2013-11-1108HRZZ
SINTEZA I CITOSTATSKA ISPITIVANJA BIBLIOTEKE NOVIH DUŠIKOVIH HETEROCIKLA-SCIENcENTRYSilvana Raić-MalićIP-2013-11-5596HRZZ
Depositing User: Dijana Žilić
Date Deposited: 10 Nov 2017 16:22
Last Modified: 10 Nov 2017 16:22
URI: http://fulir.irb.hr/id/eprint/3663
DOI: 10.3762/bjoc.13.232

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