Screening the Synthesis of 2-Substituted-2-oxazolines
-
Kempe, Kristian; Lobert, Matthias; Hoogenboom, Richard; Schubert, Ulrich S.
- Abstract:
- 2-Oxazolines are well-known organic compounds which are included in a variety of complex biologically
active structures and play a role as catalyst ligands and intermediates for functional compounds. In addition,
2-oxazolines serve as monomers for the synthesis of substituted poly(imine)s by cationic ring-opening
polymerization. For the latter application, the feasibility of preparing new 2-substituted-2-oxazolines was
investigated using an automated synthesizer. The reaction of various nitriles with 2-aminoethanol under
Lewis acid catalysis was utilized for this purpose. Twenty-nine different substituted nitriles were selected
out of more than 2000 commercial available nitriles to form the corresponding 2-oxazolines. At first, the
reaction conditions were optimized for seven nitriles with regard to solvent and catalyst, including
reproducibility tests in an automated parallel robot system. In the next step, the synthesis of all 29 2-oxazolines
was screened in an automated parallel manner, whereby the reactions were monitored by GC-MS
measurements providing novel insights in the scope of this synthesis route. These insights resulting from
the high-throughput screening were validated by performing representative larger-scale syntheses of selected
2-oxazolines.
- Year:
- 2009
- Type of Publication:
- Article
- Journal:
- Journal of Combinatorial Chemistry
- Volume:
- 11
- Pages:
- 274 - 280