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Intramolecular hydroamination of alkynic sulfonamides catalyzed by a gold-triethynylphosphine complex: Construction of azepine frameworks by 7-exo-dig cyclization.

ABSTRACT: The gold-catalyzed, seven-membered ring forming, intramolecular hydroamination of alkynic sulfonamides has been investigated. The protocol, with a semihollow-shaped triethynylphosphine as a ligand for gold, allowed the synthesis of a variety of azepine derivatives, which are difficult to access by other methods. Both alkynic sulfoamides with a flexible linear chain and the benzene-fused substrates underwent 7-exo-dig cyclization to afford the nitrogen-containing heterocyclic seven-membered rings, such as tetrahydroazepine and dihydrobenzazepine, in good yields.

SUBMITTER: Ito H 

PROVIDER: S-EPMC3167492 | biostudies-literature | 2011

REPOSITORIES: biostudies-literature

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Intramolecular hydroamination of alkynic sulfonamides catalyzed by a gold-triethynylphosphine complex: Construction of azepine frameworks by 7-exo-dig cyclization.

Ito Hideto H   Harada Tomoya T   Ohmiya Hirohisa H   Sawamura Masaya M  

Beilstein journal of organic chemistry 20110708

The gold-catalyzed, seven-membered ring forming, intramolecular hydroamination of alkynic sulfonamides has been investigated. The protocol, with a semihollow-shaped triethynylphosphine as a ligand for gold, allowed the synthesis of a variety of azepine derivatives, which are difficult to access by other methods. Both alkynic sulfoamides with a flexible linear chain and the benzene-fused substrates underwent 7-exo-dig cyclization to afford the nitrogen-containing heterocyclic seven-membered rings  ...[more]

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