Issue 4, 2007
From the journal:

Green Chemistry

Synthesis of bi- and tricyclic β-lactam libraries in aqueous medium†

Iván Kanizsai,a   Szilvia Gyónfalvi,a   Zsolt Szakonyi,a   Reijo Sillanpääb  and  Ferenc Fülöp*a  

* Corresponding authors

a Institute of Pharmaceutical Chemistry, University of Szeged, POB 427, Szeged, Hungary
E-mail: fulop@pharm.u-szeged.hu
Fax: +36-62-545705
Tel: +36-62-545564

b Department of Chemistry, University of Jyväskylä, POB 35, Jyväskylä, Finland

Abstract

Water as a solvent is not only inexpensive and environmentally benign, but may allow good reactivity. The present work focuses on the application of a modified Ugi reaction, i.e. the Ugi four-centre three-component reaction (U-4C-3CR), in aqueous medium to construct β-lactam libraries. All the attempted reactions could be successfully performed in water. The reaction conditions under which the precipitation process was effective were investigated; no further work-up or purification was necessary. In several cases when less water-soluble β-amino acids were used, the precipitated products were isolated easily by simple filtration. In other cases, evaporation of the solvent was appropriate for isolation; when the product was crystalline, recrystallization was necessary to obtain the pure final compounds. In water, the yields were higher as compared with the reactions in organic solvents. When bicyclic β-amino acids and the bulky tert-butyl isocyanide were used as starting materials, noteworthy increases in diastereoselectivity were observed.

Graphical abstract: Synthesis of bi- and tricyclic β-lactam libraries in aqueous medium

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Article information

DOI
https://doi.org/10.1039/B613117D
Article type
Paper
Submitted
12 Sep 2006
Accepted
21 Dec 2006
First published
18 Jan 2007

Green Chem., 2007,9, 357-360

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Synthesis of bi- and tricyclic β-lactam libraries in aqueous medium

I. Kanizsai, S. Gyónfalvi, Z. Szakonyi, R. Sillanpää and F. Fülöp, Green Chem., 2007, 9, 357 DOI: 10.1039/B613117D

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