Novel synthetic route of aryl-aminopyrazine

We report a novel synthetic route of aryl-aminopyrazine through a new cyclization reaction by using a hydroxylamine. Starting from Boc-glycine and aminonitrile, the aminopyrazine ring was prepared in several steps. After trifluoromethane sulfonylation of the aminopyrazinone, the resultant triflate w...

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Bibliographic Details
Published inTetrahedron Vol. 60; no. 4; pp. 835 - 840
Main Authors Kuse, Masaki, Kondo, Nobuhiro, Ohyabu, Yuki, Isobe, Minoru
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.01.2004
Elsevier
Subjects
Aminopyrazine
Chemistry
Chemistry, Organic
Hydroxylamine
Physical Sciences
Science & Technology
Suzuki coupling
Suzuki coupling
Aminopyrazine
Hydroxylamine
COELENTERAZINE
WATASENIA-SCINTILLANS
ammopyrazine
CROSS-COUPLING REACTION
hydroxylamine
LOW-TEMPERATURE
LUMINOUS SQUID
C-13-DEHYDROCOELENTERAZINE
PHOTOPROTEIN AEQUORIN
SQUID SYMPLECTOTEUTHIS-OUALANIENSIS
PHOTOOXYGENATION
suzuki coupling
BIOLUMINESCENCE
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Summary:We report a novel synthetic route of aryl-aminopyrazine through a new cyclization reaction by using a hydroxylamine. Starting from Boc-glycine and aminonitrile, the aminopyrazine ring was prepared in several steps. After trifluoromethane sulfonylation of the aminopyrazinone, the resultant triflate was subjected to Suzuki–Miyaura coupling reaction with aryl boronic acid to afford coelenteramine. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2003.11.052