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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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
Online AccessGet full text
ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/acs.orglett.7b01759

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Abstract 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.
AbstractList 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, R followed by a 7-endo-dig cyclizatiOri to give 1,6-dihydrocyclohepta[b]pyrroles in good. yields: The direct synthesis of"cyclohepta[b]indoles using indole nucleophiles has also been reported:
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.
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.
Author Yoshida, Yusuke
Ohno, Hiroaki
Hamada, Naoka
Oishi, Shinya
AuthorAffiliation Kyoto University
Graduate School of Pharmaceutical Sciences
AuthorAffiliation_xml – name: Graduate School of Pharmaceutical Sciences
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  givenname: Naoka
  surname: Hamada
  fullname: Hamada, Naoka
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  givenname: Yusuke
  surname: Yoshida
  fullname: Yoshida, Yusuke
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  givenname: Shinya
  orcidid: 0000-0002-2833-2539
  surname: Oishi
  fullname: Oishi, Shinya
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  givenname: Hiroaki
  orcidid: 0000-0002-3246-4809
  surname: Ohno
  fullname: Ohno, Hiroaki
  email: hohno@pharm.kyoto-u.ac.jp
BackLink https://www.ncbi.nlm.nih.gov/pubmed/28692275$$D View this record in MEDLINE/PubMed
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Issue 14
Keywords BALDWIN RULES
CYCLIZATIONS
1,4-DIYNES
HETEROCYCLES
COMPLEXES
REGIOSELECTIVE SYNTHESIS
PYRROLES
ALKYNES
DERIVATIVES
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Snippet A gold-catalyzed cascade reaction of skipped diynes (1,4-diynes) and pyrroles has been developed. This reaction proceeds by the consecutive regioselective...
A gold-catalyzed cascade reaction of skipped diynes (1,4-diynes), and pyrroles has been developed. This reaction proceeds by the consecutive regioselective...
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SubjectTerms alkynes
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
indoles
Lewis bases
Physical Sciences
pyrroles
regioselectivity
Science & Technology
Title Gold-Catalyzed Cascade Reaction of Skipped Diynes for the Construction of a Cyclohepta[b]pyrrole Scaffold
URI http://dx.doi.org/10.1021/acs.orglett.7b01759
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https://www.ncbi.nlm.nih.gov/pubmed/28692275
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