The pyroglutamate hydantoin rearrangement

被引：27

作者：

Dieltiens, Nicolai

Claeys, Diederica D.

Zhdankin, Viktor V.

Nemykin, Victor N.

Allaert, Bart

Verpoort, Francis

Stevens, Christian V.

机构：

[1] Univ Ghent, Fac Biosci Engn, Dept Organ Chem, Res Grp Synbioc, B-9000 Ghent, Belgium

[2] Univ Minnesota, Dept Chem, Duluth, MN 55812 USA

[3] Univ Ghent, Dept Inorgan & Phys Chem, Div Organomet & Catalysis, B-9000 Ghent, Belgium

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 11期

关键词：

nitrogen heterocycles; lactams; fused-ring systems; rearrangement; pyroglutamates; hydantoins; ring-closing metathesis; isocyanates;

D O I：

10.1002/ejoc.200600051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

When a mixture of a pyroglutamate and an isocyanate in THF is treated with NaH, a ring transformation occurs leading to functionalised hydantoins. The novel reaction involves a ring-closing ring-opening sequence providing a new and straightforward access to an interesting class of heterocyclic compounds. Furthermore, starting from pyroglutamates allows the synthesis of highly substituted hydantoins under very mild conditions. This ring transformation in combination with ring-closing metathesis is used in a four-step reaction sequence for the synthesis of multi-functionalised bicyclic hydantoin derivatives. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

引用

页码：2649 / 2660

页数：12

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