Synthesis of Pyrazines from Rhodium-Catalyzed Reaction of 2H‑Azirines with N‑Sulfonyl 1,2,3-Triazoles

An efficient synthetic route to a wide range of trisubstituted pyrazines is developed from Rh-catalyzed reaction of 2H-azirines with N-sulfonyl-1,2,3-triazoles through the elimination of nitrogen molecule and arylsulfinic acid. The present reaction proceeds through formation of in situ generated dih...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 80; no. 4; pp. 2376 - 2383
Main Authors Ryu, Taekyu, Baek, Yonghyeon, Lee, Phil Ho
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.02.2015
Amer Chemical Soc
Subjects
Azirines - chemistry
Catalysis
Chemistry
Chemistry, Organic
Molecular Structure
Organometallic Compounds - chemistry
Physical Sciences
Pyrazines - chemical synthesis
Pyrazines - chemistry
Rhodium - chemistry
Science & Technology
Triazoles - chemistry
CYCLOADDITION
AZIDES
ANNULATION
CONVERSION
TERMINAL ALKYNES
H INSERTION
TRANSANNULATION
PYRROLES
1-SULFONYL-1,2,3-TRIAZOLES
TRIAZOLES
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Summary:An efficient synthetic route to a wide range of trisubstituted pyrazines is developed from Rh-catalyzed reaction of 2H-azirines with N-sulfonyl-1,2,3-triazoles through the elimination of nitrogen molecule and arylsulfinic acid. The present reaction proceeds through formation of in situ generated dihydropyrazines.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b00036