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Thomas J.,Molecular Design and Synthesis | Goyvaerts V.,Molecular Design and Synthesis | Liekens S.,Rega Institute for Medical Research | Dehaen W.,Molecular Design and Synthesis
Chemistry - A European Journal | Year: 2016

Functionalized 1,2,3-triazole heterocycles have been known for a long time and hold an extraordinary potential in diverse research areas ranging from medicinal chemistry to material science. However, the scope of therapeutically important 1-substituted 4-acyl-1H-1,2,3-triazoles is much less explored, probably due to the lack of synthetic methodologies of good scope and practicality. Here, we describe a practical and efficient one-pot multicomponent reaction for the synthesis of α-ketotriazoles from readily available building blocks such as methyl ketones, N,N-dimethylformamide dimethyl acetal, and organic azides with 100 % regioselectivity. This reaction is enabled by the in situ formation of an enaminone intermediate followed by its 1,3-dipolar cycloaddition reaction with an organic azide. We effectively utilized the developed strategy for the derivatization of various heterocycles and natural products, a protocol which is difficult or impossible to realize by other means. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Bajpe S.R.,U-Systems | Kirschhock C.E.A.,U-Systems | Aerts A.,U-Systems | Breynaert E.,U-Systems | And 4 more authors.
Chemistry - A European Journal | Year: 2010

(Figure presented) The molecular steps involved in the self-assembly of Cu3(BTC)2 (BTC=1,3,5-benzenetricarboxylic acid) metal-organic frameworks that enclose Keggin-type H3PW 12O40 heteropolyacid molecules were unraveled by using solution 17O, 31P, and 183WNMR spectroscopy, small-angle X-ray scattering, near-IR spectroscopy, and dynamic light scattering. In aqueous solution, complexation of Cu2+ ions with Keggin-type heteropolyacids was observed. Cu2+ ions are arranged around the Keggin structure so that linking through benzenetricarboxylate groups results in the formation of the Cu3(BTC)2 MOF structure HKUST-1. This is a unique instance in which a templating mechanism that relies on specific molecular-level matching and leads to explicit nanoscale building units can be observed in situ during formation of the synthetic nanoporous material. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

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