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

✍ Scribed by Csaba Wéber; Ádám Demeter; Györgyi I. Szendrei; István Greiner

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
108 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new procedure for the solid-phase synthesis of 2,6-and 2,7-diamino-4(3H)-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(3H)-quinazolinone moiety.

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