Copper-catalyzed domino reaction between 1-(2-halophenyl)methanamines and amidines or imidates for the synthesis of 2-substituted quinazolines
- Publication Type
- Journal contribution (peer reviewed)
- Authors
- Omar, M. A.; Conrad, J.; Beifuss, U.
- Year of publication
- 2014
- Published in
- Tetrahedron
- Band/Volume
- 3061-3072/
- DOI
- 10.1016/j.tet.2014.02.066
The CuI-catalyzed domino reaction between 1-(2-bromophenyl)methanamines and amidines using K3PO4 as the base, pivalic acid as the additive, and aerial oxygen as the oxidant gives access to substituted quinazolines in a single step with yields in the range between 43 and 90%. It is assumed that the reaction proceeds as a Cu(I)-catalyzed intermolecular N-arylation followed by an intramolecular nucleophilic substitution and a Cu(II)-catalyzed oxidation. The amidines can be replaced with imidates and the reaction can also be run with 1-(2-iodophenyl)methanamine.