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Solid-phase synthesis of 1,3-dialkyl quinazoline-2,4-diones

โœ Scribed by Brad O. Buckman; Raju Mohan

Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
205 KB
Volume
37
Category
Article
ISSN
0040-4039

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๐Ÿ“œ SIMILAR VOLUMES

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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

ChemInform Abstract: Solid-Phase Synthes
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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

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A traceless synthesis of 1,2,4-triazolidine-3,5-diones has been achieved through cyclo-elimination from solid-phase. This traceless cyclo-elimination release step is induced by catalytic amount of base or by simply refluxing the urea carbamate intermediate.