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A versatile cyclodehydration reaction for the synthesis of isoquinoline and beta-carboline derivatives.

ABSTRACT: The direct conversion of various amides to isoquinoline and beta-carboline derivatives via mild electrophilic amide activation, with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine, is described. Low-temperature amide activation followed by cyclodehydration upon warming provides the desired products with short overall reaction times. The successful use of nonactivated and halogenated phenethylene derived amides, N-vinyl amides, and optically active substrates is noteworthy.

SUBMITTER: Movassaghi M

PROVIDER: S-EPMC2692836 | biostudies-literature | 2008 Aug

REPOSITORIES: biostudies-literature

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A versatile cyclodehydration reaction for the synthesis of isoquinoline and beta-carboline derivatives.

Movassaghi Mohammad M Hill Matthew D MD

Organic letters 20080719 16

The direct conversion of various amides to isoquinoline and beta-carboline derivatives via mild electrophilic amide activation, with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine, is described. Low-temperature amide activation followed by cyclodehydration upon warming provides the desired products with short overall reaction times. The successful use of nonactivated and halogenated phenethylene derived amides, N-vinyl amides, and optically active substrates is noteworthy ...[more]

PMID: 18642832

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