Issue 5, 2002

Synthesis of homochiral amino acid pyrazine and pyrrole analogues of glutamateantagonists

Abstract

Use of the acid 7 and the aldehydes 23a and 23b in “ring switching” reactions with hydrazines has given β-(1-aminopyrrole)amino acids as kinetic products. The products from the reaction of the aldehyde have been converted into β-(pyrazine)amino acids by an equilibration–dehydration sequence. A variety of homochiral reduced heterocyclic amino acids containing two chiral centres has been prepared in this way. Some of the product amino acids undergo “reverse ring switching” to the corresponding pyroglutamic acid derivatives.

Graphical abstract: Synthesis of homochiral amino acid pyrazine and pyrrole analogues of glutamate antagonists

Article information

Article type
Paper
Submitted
30 Nov 2001
Accepted
16 Jan 2002
First published
07 Feb 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 613-621

Synthesis of homochiral amino acid pyrazine and pyrrole analogues of glutamate antagonists

A. Dinsmore, P. M. Doyle, M. Steger and D. W. Young, J. Chem. Soc., Perkin Trans. 1, 2002, 613 DOI: 10.1039/B110979K

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