Solid-phase synthesis of 2,6- and 2,7-diamino-4(3 H)-quinazolinones via palladium-catalyzed amination

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 positi...

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Bibliographic Details
Published in:Tetrahedron letters 2003-09, Vol.44 (40), p.7533-7536
Main Authors: Wéber, Csaba, Demeter, Ádám, Szendrei, Györgyi I., Greiner, István
Format: Article
Language:English
Subjects:
4(3 H)-quinazolinones
amination
palladium
solid-phase synthesis
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Summary: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. X=Cl, Br; R=H, MeO; NR 1R 2 and NR 3R 4=primary or secondary amines.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(03)01876-8