Gold-Catalyzed Cascade Reaction of Skipped Diynes for the Construction of a Cyclohepta[b]pyrrole Scaffold

A gold-catalyzed cascade reaction of skipped diynes (1,4-diynes) and pyrroles has been developed. This reaction proceeds by the consecutive regioselective hydroarylation of two alkynes with a pyrrole, followed by a 7-endo-dig cyclization to give 1,6-dihydrocyclo­hepta­[b]­pyrroles in good yields. Th...

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Bibliographic Details
Published inOrganic letters Vol. 19; no. 14; pp. 3875 - 3878
Main Authors Hamada, Naoka, Yoshida, Yusuke, Oishi, Shinya, Ohno, Hiroaki
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.07.2017
Amer Chemical Soc
Subjects
alkynes
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
indoles
Lewis bases
Physical Sciences
pyrroles
regioselectivity
Science & Technology
BALDWIN RULES
CYCLIZATIONS
1,4-DIYNES
HETEROCYCLES
COMPLEXES
REGIOSELECTIVE SYNTHESIS
PYRROLES
ALKYNES
DERIVATIVES
HYDROARYLATION
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Summary:A gold-catalyzed cascade reaction of skipped diynes (1,4-diynes) and pyrroles has been developed. This reaction proceeds by the consecutive regioselective hydroarylation of two alkynes with a pyrrole, followed by a 7-endo-dig cyclization to give 1,6-dihydrocyclo­hepta­[b]­pyrroles in good yields. The direct synthesis of cyclohepta­[b]­indoles using indole nucleophiles has also been reported.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.7b01759