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Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides.


ABSTRACT: Selective C-H amidation of 1H-indoles at the C3 position is reported as a direct entry to biologically important 3-aminoindoles. This transformation is achieved using novel N-[(benzenesulfonyl)oxy]amides as electrophilic nitrogen agents in the presence of ZnCl2. Interestingly, analogous reactions in the absence of ZnCl2 resulted in the formation of indole aminal products.

SUBMITTER: Ortiz GX 

PROVIDER: S-EPMC5685508 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides.

Ortiz Gerardo X GX   Hemric Brett N BN   Wang Qiu Q  

Organic letters 20170310 6


Selective C-H amidation of 1H-indoles at the C3 position is reported as a direct entry to biologically important 3-aminoindoles. This transformation is achieved using novel N-[(benzenesulfonyl)oxy]amides as electrophilic nitrogen agents in the presence of ZnCl<sub>2</sub>. Interestingly, analogous reactions in the absence of ZnCl<sub>2</sub> resulted in the formation of indole aminal products. ...[more]

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