A versatile method for the solid-phase synthesis of differentially substituted quinazolin-4(3H)-ones has been developed using immobilized arylguanidines. The latter were obtained by treating the amino group of polymer-linked anthranilamide with isothiocyanates followed by coupling with secondary ami
Traceless synthesis of 3H-quinazolin-4-ones via a combination of solid-phase and solution methodologies
✍ Scribed by Donogh J.R. O'Mahony; Viktor Krchňák
- Book ID
- 104232309
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 119 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A solid-phase traceless synthesis of quinazolin-4-ones is described. An aldehyde functionalized resin was reductively aminated with primary amines, and the resin-bound secondary amine acylated with o-nitro-benzoic acids. The nitro group was reduced with tin(II) chloride, and the aniline acylated with acid anhydrides. Acidolytic cleavage afforded a diamide, which was cyclized in solution phase to the 3H-quinazolin-4-one removing the trace of the linker.
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