Synthesis of Polycyclic Imidazolidinones via Amine Redox-Annulation

α-Ketoamides undergo redox-annulations with cyclic secondary amines, such as 1,2,3,4-tetrahydroisoquinoline, pyrrolidine, piperidine, and morpholine. Catalytic amounts of benzoic acid significantly accelerate these transformations. This approach provides polycyclic imidazolidinone derivatives in typ...

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Bibliographic Details
Published inOrganic letters Vol. 19; no. 23; pp. 6424 - 6427
Main Authors Zhu, Zhengbo, Lv, Xin, Anesini, Jason E, Seidel, Daniel
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.12.2017
Amer Chemical Soc
Subjects
Amines - chemistry
Benzoic Acid - chemistry
Catalysis
Chemistry
Chemistry, Organic
Imidazolidines - chemical synthesis
Letter
Molecular Structure
Oxidation-Reduction
Physical Sciences
Polycyclic Compounds - chemical synthesis
Science & Technology
AZOMETHINE YLIDE ROUTE
X=Y-ZH COMPOUNDS
ALPHA-AMINATION
IMINIUM ION ROUTE
POTENTIAL 1,3-DIPOLES
1,3-DIPOLAR CYCLOADDITION REACTIONS
C-H FUNCTIONALIZATION
SECONDARY-AMINES
INTERMOLECULAR 3+2 CYCLOADDITION
CYCLIC AMINES
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Summary:α-Ketoamides undergo redox-annulations with cyclic secondary amines, such as 1,2,3,4-tetrahydroisoquinoline, pyrrolidine, piperidine, and morpholine. Catalytic amounts of benzoic acid significantly accelerate these transformations. This approach provides polycyclic imidazolidinone derivatives in typically good yields.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b03309