Csaba Weber, Á. Demeter, G. Szendrei
Sep 29, 2003
Citations
0
Influential Citations
17
Citations
Journal
Tetrahedron Letters
Abstract
Abstract A new procedure for the solid-phase synthesis of 2,6- and 2,7-diamino-4(3 H )-quinazolinones is described. The method involves coupling of 2,4,6- and 2,4,7-trichloroquinazoline to a solid support via benzyl alcohol type linkers, subsequent displacement of chlorine at C-2 then at the C-6 or C-7 positions by amines ( Fig. 1 ) and the cleavage of the products from the resin. The palladium-catalyzed amination of C-6 and C-7 positions with a representative set of amines in the presence of 2-(di- t -butylphosphino)biphenyl (DTBPBP), P( t -Bu) 3 and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) ligands has been investigated. This method should prove to be a useful tool for constructing combinatorial libraries containing the 4(3 H )-quinazolinone moiety.