Progress in the synthesis of OPC-15161: Easy access to dioxygenated pyrazine N-oxide structure

Citation
H. Tone et al., Progress in the synthesis of OPC-15161: Easy access to dioxygenated pyrazine N-oxide structure, ORG PROC R, 4(5), 2000, pp. 312-317
Citations number
7
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC PROCESS RESEARCH & DEVELOPMENT
ISSN journal
1083-6160 → ACNP
Volume
4
Issue
5
Year of publication
2000
Pages
312 - 317
Database
ISI
SICI code
1083-6160(200009/10)4:5<312:PITSOO>2.0.ZU;2-9
Abstract
An improved synthetic route to OPC-15161 (1), a novel inhibitor of superoxi de anion generation, is described. Choice of the protecting group is the ke y to the second-generation synthesis. Usefulness of the 2-cyanoethyl (CE)-p rotecting group in our process research is emphasized in comparison with th at of other protecting groups. This process can be carried out in four step s with 40% overall yield from tryptophan methyl ester, which also opens a g eneral route for the preparation of the related 5-alkoxypyrazin-2(1H)-one 4 -oxides.