Synthesis of chiral 1,6,8-trioxoperhydropyrazino[1,2-c]pyrimidines as novel highly functionalized scaffolds for peptidomimetics

Abstract:

The synthesis of novel chiral 4,7-disubstituted- and 2,4,7-trisubstituted-1,6,8-trioxoperhydropyrazino[1,2-c]pyrimidines from suitably protected TrpΨ[CH(CN)NH]Asp pseudodipeptides is described. This synthesis involves the cyclization of the Ψ[CH(CN)NH] pseudodipeptides, via catalytic hydrogenation and in situ lactamization, to give 3,5-disubstituted-2-oxopiperazine derivatives, which upon reaction with isocyanates, followed by base-catalyzed cyclization lead to the target 4,7-disubstituted-1,6,8-trioxoperhydropyrazino[1,2-c]-pyrimidines. The alkylation of these bicyclic heterocycles gives their corresponding 2,4,7-trisubstituted derivatives. © 2002 Elsevier Science Ltd. All rights reserved.

Año de publicación:

2002

Keywords:

• 1,6,8-trioxoperhydropyrazino[1,2-c]pyrimidines
• Lactams
• Urea derivatives
• Peptidomimetics
• 3,5-disubstituted-2-oxopiperazines
• Nitrogen bridged bicyclic heterocycles
• Ψ[CH(CN)NH] pseudodipeptides

Fuente:

scopus