Rh()-Catalyzed tandem indole C4-arylamination/annulation with anthranils: access to indoloquinolines and their application in photophysical studies

An efficient Rh( iii )-catalyzed straightforward strategy was developed for the tandem C4 arylamination/annulation of indole derivatives with anthranil to provide indoloquinoline moieties. This method is simple and regioselective with a wide scope and functional group tolerance. Mechanistic studies...

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Published inChemical communications (Cambridge, England) Vol. 56; no. 9; pp. 144 - 1443
Main Authors Biswas, Aniruddha, Bera, Satabdi, Poddar, Puja, Dhara, Dibakar, Samanta, Rajarshi
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 30.01.2020
Royal Society of Chemistry
Subjects
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Crystallography
Derivatives
Functional groups
Organic chemistry
Physical Sciences
Science & Technology
DIRECTING GROUP
FUNCTIONALIZATION
AMINATION
OLEFINATION
CATALYZED DIRECT
ANNULATIVE PI-EXTENSION
C4-ALKYLATION
ALKYNES
BOND
C-H ACTIVATION
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Summary:An efficient Rh( iii )-catalyzed straightforward strategy was developed for the tandem C4 arylamination/annulation of indole derivatives with anthranil to provide indoloquinoline moieties. This method is simple and regioselective with a wide scope and functional group tolerance. Mechanistic studies revealed the important role of the newly installed azacycle in the conversion of O -protected aldoximes to their cyano derivatives. Studies were carried out to explore the promising photophysical properties of the obtained indoloquinoline derivatives. An efficient Rh( iii )-catalyzed straightforward strategy was developed for the site-selective tandem C4 arylamination/annulation of indole derivatives with anthranil to provide indoloquinoline moieties.
Bibliography:Electronic supplementary information (ESI) available. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
10.1039/c9cc08372c
1944062
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc08372c