Issue 14, 2012

Synthesis of quinolinesvia Friedländer reaction catalyzed by CuBTC metal–organic-framework

Abstract

Friedländer condensation between 2-aminoaryl ketones and different carbonyl compounds, catalyzed by CuBTC was investigated by a combination of various experimental techniques and by density functional theory based modelling. CuBTC exhibiting hard Lewis acid character showed highly improved catalytic activity when compared with other molecular sieves showing high concentraion of Lewis acid sites, e.g. in BEA and (Al)SBA-15. Polysubstituted quinolines were synthesized via a Friedländer reaction catalyzed by CuBTC under the solvent-free conditions. High concentration of active sites in CuBTC together with the concerted effect of a pair of adjacent Cu2+ coordinatively unsaturated active sites are behind a very high quinoline yield reached within a short reaction time. Results reported here make CuBTC a promising catalyst for other Lewis acid-promoted condensations, including those leading to biologically active compounds with a particular relevance for the pharmaceutical industry. The mechanism of a catalyzed Friedländer reaction investigated computationally is also reported.

Graphical abstract: Synthesis of quinolines via Friedländer reaction catalyzed by CuBTC metal–organic-framework

Article information

Article type
Paper
Submitted
19 Okt. 2011
Accepted
09 Dec. 2011
First published
01 Febr. 2012

Dalton Trans., 2012,41, 4036-4044

Synthesis of quinolines via Friedländer reaction catalyzed by CuBTC metal–organic-framework

E. Pérez-Mayoral, Z. Musilová, B. Gil, B. Marszalek, M. Položij, P. Nachtigall and J. Čejka, Dalton Trans., 2012, 41, 4036 DOI: 10.1039/C2DT11978A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements