C–H Activation Guided by Aromatic N–H Ketimines: Synthesis of Functionalized Isoquinolines Using Benzyl Azides and Alkynes

Aromatic N–H ketimines were in situ generated from various benzylic azides by ruthenium catalysis for the subsequent Rh-catalyzed annulation reaction with alkynes to give the corresponding isoquinolines. In contrast to conventional synthetic methods for aromatic N–H ketimines, our protocol works und...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 79; no. 19; pp. 9094 - 9103
Main Authors Gupta, Sreya, Han, Junghoon, Kim, Yongjin, Lee, Soon W, Rhee, Young Ho, Park, Jaiwook
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.10.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
UNSUBSTITUTED IMINES
ORTHO ARYLATION
RHODIUM(III)-CATALYZED SYNTHESIS
ENANTIOSELECTIVE HYDROGENATION
CATALYZED ANNULATION
EFFICIENT SYNTHESIS
BENZODIAZEPINE-RECEPTORS
BOND ACTIVATION
INTERNAL ALKYNES
CYCLIZATION
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Summary:Aromatic N–H ketimines were in situ generated from various benzylic azides by ruthenium catalysis for the subsequent Rh-catalyzed annulation reaction with alkynes to give the corresponding isoquinolines. In contrast to conventional synthetic methods for aromatic N–H ketimines, our protocol works under mild and neutral conditions, which enabled the synthesis of isoquinolines having various functionalities such as carbonyl, ester, alkenyl, and ether groups. In addition, the imidates generated from α-azido ethers were successfully used for the synthesis of 1-alkoxyisoquinolines.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo501465q