Copper-catalyzed synthesis of quinazolines in water starting from o-bromobenzylbromides and benzamidines.
Water makes it possible: The Cu(2)O-catalyzed reaction between easily available o-bromobenzylbromides and benzamidines by using Cs(2)CO(3) as the base and N,N'-dimethylethylenediamine (DMEDA) as the additive in water as the solvent gives access to substituted quinazolines in a single step with yields ranging from 57 to 85 % (see scheme).
Institut für Chemie, Universität Hohenheim, Garbenstr. 30, 70599 Stuttgart, Deutschland.
Chandi C
CC
Malakar
Alevtina
A
Baskakova
Jürgen
J
Conrad
Uwe
U
Beifuss
D001550:Benzamidines / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D005029:Ethylenediamines / Q000737:chemistry*; D015394:Molecular Structure; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry*; D014867:Water
D001550:Benzamidines; D001593:Benzyl Compounds; D005029:Ethylenediamines; D011799:Quinazolines; D014867:Water; C027450:dimethylethylenediamine; D003300:Copper