Ru-NHC Catalyzed Domino Reaction of Carbonyl Compounds and Alcohols: A Short Synthesis of Donaxaridine

Direct α-alkylation of amides and the synthesis of C3-alkylated 3-hydroxyindolin-2-one/2-substituted-2-hydroxy-3,4-dihydronaphthalen-1­(2H)-one derivatives from 2-oxindole/1-teralone were reported using primary alcohols in the presence of Ru-NHC catalyst in a one pot condition under the borrowing hy...

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Bibliographic Details
Published in:ACS omega 2017-11, Vol.2 (11), p.8234-8252
Main Authors: Bisht, Girish Singh, Chaudhari, Moreshwar Bhagwan, Gupte, Vruta Sunil, Gnanaprakasam, Boopathy
Format: Article
Language:English
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Summary:Direct α-alkylation of amides and the synthesis of C3-alkylated 3-hydroxyindolin-2-one/2-substituted-2-hydroxy-3,4-dihydronaphthalen-1­(2H)-one derivatives from 2-oxindole/1-teralone were reported using primary alcohols in the presence of Ru-NHC catalyst in a one pot condition under the borrowing hydrogen method. In the case of inert conditions, 2-oxindole/1-teralone exclusively forms the C3-alkylated product. Whereas, allowing this reaction mixture to occur under an air atmosphere predominantly forms C3-alkylated 3-hydroxyindolin-2-one via domino C–H alkylation and aerobic C–H hydroxylation. This Ru-NHC catalyst is easily accessible, air stable, and phosphine free. Using this method, synthesis of 2-oxindole based natural products such as Donaxaridine was accomplished.
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.7b01152