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A practical solid phase synthesis of quinazoline-2,4-diones

โœ Scribed by Hui Shao; Marcus Colucci; Shaojing Tong; Hesheng Zhang; Arlindo L. Castelhano


Book ID
108387033
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
219 KB
Volume
39
Category
Article
ISSN
0040-4039

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An efficient solid phase synthesis of chiral quinazolinediones is described. Immobilized amino acid based urea derivatives 3 undergo a racemization-free heterocyclization upon gentle heating in presence of tetramethylguanidinc to afford fused pyrimidine-2,4-diones 6, which are smoothly NJ-alkylated

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Solid-Phase Synthesis of Chiral 3-Substituted Quinazoline-2,4-diones. -A series of N-urethane precursors such as (I) or (III) are prepared and subjected to cyclization in the presence of base (DBU, NaOH or NEt3). The desired quinazolines are obtained in good to excellent yield without racemization.

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We have developed a method for the solid-phase synthesis of quinazoline-2,4-diones with various substituents on the aromatic ring. Although there have been numerous reports of the solid-phase synthesis of quinazoline-2,4-diones, they were not applicable to the synthesis of the quinazoline-2,4-diones