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The Pyroglutamate Hydantoin Rearrangement
Author(s) -
Dieltiens Nicolai,
Claeys Diederica D.,
Zhdankin Viktor V.,
Nemykin Victor N.,
Allaert Bart,
Verpoort Francis,
Stevens Christian V.
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600051
Subject(s) - chemistry , hydantoin , isocyanate , ring (chemistry) , ring closing metathesis , metathesis , sequence (biology) , stereochemistry , bicyclic molecule , transformation (genetics) , salt metathesis reaction , combinatorial chemistry , organic chemistry , polymer , biochemistry , polyurethane , polymerization , gene
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.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)