Abstract
The reaction of 3-(2-bromoethyl)quinazolin-4(3H)-one with ethyl- and n-propylamine gave abnormal fused 3-alkyl-4-alkyliminoquinazolines via a Dimroth-type rearrangement, as well as normal substituted 3-(2-alkylaminoethyl) derivatives in methanol. The reaction of 3-(2-bromoethyl)-5,6,7,8-tetrahydroquinazolin-4(3H)-one with primary alkylamines was also investigated for the scope of this rearrangement reaction.
ACKNOWLEDGMENTS
We are grateful to the SC-NMR Laboratory of Okayama University for 200-MHz 1H NMR experiments. We also thank Prof. Jeffrey W. Bode (Departements Chemie und Angewandte Biowissenschaften, ETH, Zürich) for helpful comments on the manuscript.
Notes
a 10 mol equiv was used.