I2-catalyzed synthesis of 3-aminopyrrole with homopropargylic amines and nitrosoarenes

The synthesis of 3-aminopyrrole using the amination reagent nitrosoarenes and homopropargylic amines catalyzed by I2 through cyclization and amination has been developed. This protocol features excellent functional group tolerance and mild reaction conditions, yielding 3-aminopyrroles in moderate to...

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Published inChemical communications (Cambridge, England) Vol. 60; no. 27; pp. 3701 - 3704
Main Authors Qin, Jiaze, Jiang, Shixuan, Luo, Xiaofeng, Wang, Tianqiang, Liu, Peihua, Yuan, Bingxiang, Yan, Rulong
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.03.2024
Royal Society of Chemistry
Subjects
Amines
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Functional groups
Oxidizing agents
Physical Sciences
Reagents
Science & Technology
ALPHA-AMINATION
HETEROARENES
O BOND-CLEAVAGE
REDUCTIVE ACYLATION
PYRROLYLAMIDES
ONE-POT
DNA
C-H AMIDATION
ANDROGEN ANTAGONISTS
CATALYZED ELECTROPHILIC AMINATION
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Summary:The synthesis of 3-aminopyrrole using the amination reagent nitrosoarenes and homopropargylic amines catalyzed by I2 through cyclization and amination has been developed. This protocol features excellent functional group tolerance and mild reaction conditions, yielding 3-aminopyrroles in moderate to good yields without a metal catalyst. This method realizes the construction and amination of the 3-aminopyrroles in which nitrosoarenes serve as the amine source and oxidant.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/d4cc00482e