✦ LIBER ✦
An uncatalyzed cyclo-elimination process for the release ofN3-alkylated hydantoins from solid-phase: synthesis of novel isoxazoloimidazolidinediones
✍ Scribed by Kyung-Ho Park; Mark J. Kurth
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 193 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Solid-phase regioselective nitrile oxide 1,3-dipolar cycloaddition to an o3-alkynyl ester followed by reductive 0t-N-alkylation and isocyanate cx-N-acylation delivers I and sets the stage for the uncatalyzed carbanilide cycloelimination of isoxazoloimidazolidinedione beterocycles (I--II). This traceless release step is induced by simply warming the urea ester intermediate, but requires that the N3 of the nascent hydantoin be fully substituted (I--II; Rc:/:H).