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Polystyrene-bound AlCl3 - a catalyst for the solvent-free synthesis of aryl-substituted tetrazoles
Max Schmallegger1, Mathias Wiech1, Sebastian Soritz2
1Institute of Physical and Theoretical Chemistry, Graz University of Technology Stremayrgasse 9 8010 Graz Austria schmallegger@tugraz.at g.gescheidt-demner@tugraz.at.
Abstract:
Tetrazole moieties are components of various pharmacologically active molecules. Several synthetic protocols for the synthesis of tetrazoles have been developed. Among those, the reaction of organic nitriles with azides catalyzed by Lewis acids (LAs) provides a convenient access. Nevertheless, generally rather harsh reaction conditions have to be utilized for such syntheses. We have developed a simple, solvent-free procedure which allows a convenient isolation of tetrazoles using a heterogeneous catalyst: we show that polystyrene/AlCl3 composites produce tetrazoles at reasonable yields and allow a simple work-up procedure. We have characterized the AlCl3/polystyrene composite (gas sorption, XRD, IR) and investigated its efficacy in the preparation of aryl-substituted tetrazoles. We also have evaluated MgCl2, CuCl2, and ZnCl2 as Lewis-acid catalysts, but they are clearly outperformed by AlCl3 correlating with the Lewis-acid strength on the Gutmann-Beckett scale.
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