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Solid-Phase Synthesis of Substituted 2,3-Diketopiperazines from Reduced Polyamides

โœ Scribed by Adel Nefzi; Marc A. Giulianotti; Richard A. Houghten

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
151 KB
Volume
56
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

AbstractรAn efยฎcient method for the solid phase synthesis of 1,6-disubstituted 2,3-diketopiperazine and 1,4,5-trisubstituted 2,3-diketopiperazine derivatives is described. The reduction of resin-bound acylated amino acids or resin-bound acylated dipeptides, followed by treatment with oxalyldiimidazole, affords the corresponding diketopiperazines in good yield and high purity. This is an example of a broader approach to the solid phase synthesis of individual heterocyclic compounds using peptides directly or indirectly as starting materials.

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The development of the solid-phase version of the modified Madelung indole synthesis is reported. The chemistry was initiated with the reductive amination of Bal resin using an ortho substituted aniline. The resin bound aniline was acylated with a variety of acid chlorides followed by cyclization wi