An uncatalyzed cyclo-elimination process for the release of N3- alkylated hydantoins from solid-phase: Synthesis of novel isoxazoloimidazolidinediones

Kyung Ho Park, Mark J. Kurth

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

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 delivers I and sets the stage for the uncatalyzed carbanilide cycloelimination of isoxazoloimidazolidinedione heterocycles (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; R(c) ≠ H).

Original languageEnglish (US)
Pages (from-to)5841-5844
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number32
DOIs
StatePublished - Aug 6 1999

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Hydantoins
Solid-Phase Synthesis Techniques
Carbanilides
Esters
Isocyanates
Acylation
Nitriles
Cycloaddition
Alkylation
Cycloaddition Reaction
Oxides
Urea

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

An uncatalyzed cyclo-elimination process for the release of N3- alkylated hydantoins from solid-phase : Synthesis of novel isoxazoloimidazolidinediones. / Park, Kyung Ho; Kurth, Mark J.

In: Tetrahedron Letters, Vol. 40, No. 32, 06.08.1999, p. 5841-5844.

Research output: Contribution to journalArticle

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