Tetrahedron letters

An uncatalyzed cyclo-elimination process for the release ofN 3-alkylated hydantoins from solid-phase: synthesis of novel isoxazoloimidazolidinediones

KH Park, MJ Kurth

文献索引：Park, Kyung-Ho; Kurth, Mark J. Tetrahedron Letters, 1999 , vol. 40, # 32 p. 5841 - 5844

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被引用次数: 37

摘要

Solid-phase regioselective nitrile oxide 1, 3-dipolar cycloaddition to an ω-alkynyl ester followed by reductive α-N-alkylation and isocyanate α-N-acylation deliversI and sets the stage for the uncatalyzed carbanilide cyclo-elimination of isoxazoloimidazolidinedione heterocycles (I→ II). This traceless release step is induced by simply warming the urea ester intermediate, but requires that theN3 of the nascent hydantoin be fully substituted (I→ II; ...