Transition-metal-free direct C-3 cyanation of quinoxalin-2(1H)-ones with ammonium thiocyanate as the "CN" source

A novel avenue of C-CN bond construction was facilely achieved via the TBHP-mediated oxidative coupling reaction between quinoxalin-2(1H)-one derivatives and ammonium thiocyanate without any metal catalyst. Applying this protocol, a variety of 3-cyanoquinoxalin-2(1H)-one derivatives were prepared in...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 7; no. 1; pp. 113 - 118
Main Authors Wang, Jiayang, Sun, Bin, Zhang, Liang, Xu, Tengwei, Xie, Yuanyuan, Jin, Can
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2020
Royal Society of Chemistry
Subjects
Ammonium
Catalysts
Chemistry
Chemistry, Organic
Derivatives
Organic chemistry
Physical Sciences
Regioselectivity
Science & Technology
Substrates
Thiocyanates
Transition metals
ELECTROPHILIC CYANATION
RHODIUM-CATALYZED CYANATION
TERTIARY-AMINES
H BOND CYANATION
COUPLING REACTION
ARYLATION
EFFICIENT SYNTHESIS
ARYL IODIDES
BETA-KETO-ESTERS
ALPHA-CYANATION
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Summary:A novel avenue of C-CN bond construction was facilely achieved via the TBHP-mediated oxidative coupling reaction between quinoxalin-2(1H)-one derivatives and ammonium thiocyanate without any metal catalyst. Applying this protocol, a variety of 3-cyanoquinoxalin-2(1H)-one derivatives were prepared in moderate to good yields with good functional-group tolerance under mild conditions. Additionally, this methodology featured a broad substrate scope, excellent regioselectivity and operational simplicity.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c9qo01055f