Polycyclic N-Heterocyclic Compounds, Part 68: Reactions of 3-(2-Bromoethyl)quinazolin-4(3H)-one and 3-(2-Bromoethyl)-5,6,7,8-tetrahydroquinazolin-4(3H)-one with Primary Alkylamines via a Dimroth-Type Rearrangement

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.

Keywords:

• 3-Alkyl-4-alkyliminopyrimidines
• Dimroth rearrangement
• nucleophilic aromatic substitution
• primary alkylamines
• pyrimidin-4(3H)-ones
• tandem reactions

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.