Metal-Free Iodine(III)-Promoted Synthesis of Isoquinolones

A metal-free oxidative cycloaddition reaction of substituted benzamides and alkynes has been developed for the synthesis of isoquinolones by using bis(trifluoracetoxy)iodobenzene (PIFA) and trifluoroacetic acid (TFA). Under mild conditions, a wide variety of isoquinolones were conveniently prepared...

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Published inJournal of organic chemistry Vol. 79; no. 22; pp. 10988 - 10998
Main Authors Chen, Zhi-Wei, Zhu, Yi-Zhou, Ou, Jin-Wang, Wang, Ya-Ping, Zheng, Jian-Yu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.11.2014
Amer Chemical Soc
Subjects
Alkynes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cycloaddition Reaction
Iodine - chemistry
Iodobenzenes - chemistry
Isoquinolines - chemical synthesis
Isoquinolines - chemistry
Metals - chemistry
Molecular Structure
Oxidation-Reduction
Physical Sciences
Science & Technology
Trifluoroacetic Acid - chemistry
INTRAMOLECULAR OXIDATIVE CYCLIZATION
DIRECTING GROUP
FUNCTIONALIZATION
ACID-DERIVATIVES
O BOND
ANNULATION
MEDIATED ALKYNE AMIDATION
N BOND FORMATION
C-H ACTIVATION
TOPOISOMERASE-I INHIBITORS
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Summary:A metal-free oxidative cycloaddition reaction of substituted benzamides and alkynes has been developed for the synthesis of isoquinolones by using bis(trifluoracetoxy)iodobenzene (PIFA) and trifluoroacetic acid (TFA). Under mild conditions, a wide variety of isoquinolones were conveniently prepared via oxidative annulation of simple N-methoxybenzamide and diarylacetylene or aryl/alkyl acetylene derivatives in yields up to 87%.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo5020307