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

✍ Scribed by Susana Herrero; Antonio Salgado; M.Teresa Garcı́a-López; Rosario Herranz

Book ID
104251381
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
135 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

The synthesis of novel chiral 4,7-disubstituted-and 2,4,7-trisubstituted-1,6,8-trioxoperhydropyrazino[1,2-c]pyrimidines from suitably protected TrpC[CH(CN)NH]Asp pseudodipeptides is described. This synthesis involves the cyclization of the C[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-1,6,8trioxoperhydropyrazino[1,2-c]-pyrimidines. The alkylation of these bicyclic heterocycles gives their corresponding 2,4,7-trisubstituted derivatives.

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Versatile synthesis of chiral 2-substituted-5-oxo-1,2,3,4-tetrahydro-5H-1,4-benzodiazepines as novel scaffolds for peptidomimetic building
✍ Susana Herrero; M.Teresa Garcı́a-López; Edurne Cenarruzabeitia; Joaquı́n Del Rı́ 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 206 KB

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