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Copper(I)-catalyzed nucleophilic addition of ynamides to acyl chlorides and activated N-heterocycles.

ABSTRACT: The addition of ynamides to acyl chlorides and N-heterocycles activated in situ with ethyl chloroformate has been accomplished at room temperature using copper iodide as catalyst. This economical and practical carbon-carbon bond formation provides convenient access to a variety of 3-aminoynones from aliphatic and aromatic acyl chlorides in up to 99% yield. The addition to pyridines and quinolines occurs under almost identical conditions and proceeds with good to high regioselectivity, producing the corresponding 1,2-dihydro-N-heterocycles in up to 95% yield.

SUBMITTER: Zhang P

PROVIDER: S-EPMC4017613 | biostudies-literature | 2014 May

REPOSITORIES: biostudies-literature

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Copper(I)-catalyzed nucleophilic addition of ynamides to acyl chlorides and activated N-heterocycles.

Zhang Peng P Cook Andrea M AM Liu Yang Y Wolf Christian C

The Journal of organic chemistry 20140418 9

The addition of ynamides to acyl chlorides and N-heterocycles activated in situ with ethyl chloroformate has been accomplished at room temperature using copper iodide as catalyst. This economical and practical carbon-carbon bond formation provides convenient access to a variety of 3-aminoynones from aliphatic and aromatic acyl chlorides in up to 99% yield. The addition to pyridines and quinolines occurs under almost identical conditions and proceeds with good to high regioselectivity, producing ...[more]

PMID: 24724797

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