Ru-Catalyzed Synthesis of Dihydrofuroquinolines from Azido-cyclopropyl Ketones

An efficient Ru-catalyzed synthesis of dihydrofuroquinolines from azido-cyclopropyl ketones via the reduction–cyclization–rearrangement process is reported. A plausible reaction mechanism for this process is depicted. Additionally, when the reaction was carried out under H2 (1 atm) in the presence o...

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Bibliographic Details
Published inOrganic letters Vol. 15; no. 6; pp. 1282 - 1285
Main Authors Yang, Weijun, Xu, Lijun, Chen, Zhengkai, Zhang, Lili, Miao, Maozhong, Ren, Hongjun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.03.2013
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Cyclization
Cyclopropanes - chemistry
Furans - chemical synthesis
Furans - chemistry
Heterocyclic Compounds, 3-Ring - chemical synthesis
Heterocyclic Compounds, 3-Ring - chemistry
Ketones - chemistry
Molecular Structure
Physical Sciences
Quinolines - chemical synthesis
Quinolines - chemistry
Ruthenium - chemistry
Science & Technology
FACILE SYNTHESIS
TANDEM SYNTHESIS
QUINAZOLINE
EFFICIENT ROUTE
REGIOSELECTIVE SYNTHESIS
QUINOLINES
ACID-MEDIATED REACTIONS
DERIVATIVES
CYCLIZATION
C-H
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Summary:An efficient Ru-catalyzed synthesis of dihydrofuroquinolines from azido-cyclopropyl ketones via the reduction–cyclization–rearrangement process is reported. A plausible reaction mechanism for this process is depicted. Additionally, when the reaction was carried out under H2 (1 atm) in the presence of Pd/C, 4-quinolones were obtained in excellent yields.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400223d