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

ABSTRACT: Direct ?-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.

SUBMITTER: Bisht GS

PROVIDER: S-EPMC6645123 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature

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

Bisht Girish Singh GS Chaudhari Moreshwar Bhagwan MB Gupte Vruta Sunil VS Gnanaprakasam Boopathy B

ACS omega 20171120 11

Direct α-alkylation of amides and the synthesis of C3-alkylated 3-hydroxyindolin-2-one/2-substituted-2-hydroxy-3,4-dihydronaphthalen-1(2<i>H</i>)-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 predomi ...[more]

PMID: 31457366

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