Synthesis of highly substituted indolines and indoles via intramolecular [4 + 2] cycloaddition of ynamides and conjugated enynes.

Synthesis of highly substituted indolines and indoles via intramolecular [4 + 2] cycloaddition of ynamides and conjugated enynes. Research Abstract Details 

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Synthesis of highly substituted indolines and indoles via intramolecular [4 + 2] cycloaddition of ynamides and conjugated enynes. Abstract Text:

Joshua R Dunetz,Rick L Danheiser,

Ynamides react with conjugated enynes in intramolecular [4 + 2] cycloadditions to afford substituted indolines that undergo oxidation with o-chloranil to furnish the corresponding indoles. The cycloaddition substrates are easily assembled from derivatives of 3-butynylamine by Sonogashira coupling with alkenyl halides followed by copper-catalyzed N-alkynylation with acetylenic bromides. Diynamides participate as particularly reactive 2pi components in the cycloaddition, providing access to indolines with carbon substituents at the C-7 position. Enynamides serve as 4pi components in a complementary version of the cycloaddition strategy which provides access to indoles and indolines substituted with carbon substituents at C-4. These enyne cycloadditions take place upon heating the substrates at 110-210 degrees C in toluene or 2,2,2-trifluoroethanol and in some cases can be achieved at 0 degrees C to room temperature in the presence of Lewis acids such as Me2AlCl.

Synthesis of highly substituted indolines and indoles via intramolecular [4 + 2] cycloaddition of ynamides and conjugated enynes. Publishing Authors By Initials

JR Dunetz,RL Danheiser,

For similar heterocyclic compounds: heterocyclic compounds, 2-ring: indoles research abstracts see: heterocyclic compounds: heterocyclic compounds, 2-ring: indoles research

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Synthesis of highly substituted indolines and indoles via intramolecular [4 + 2] cycloaddition of ynamides and conjugated enynes. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Journal of the American Chemical Society

VOLUME: 127

Page Numbers: 5776-7

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 27

MONTH: Apr

YEAR: 2005

Synthesis of highly substituted indolines and indoles via intramolecular [4 + 2] cycloaddition of ynamides and conjugated enynes. Information

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LANGUAGE: eng

NlmUniqueID: 7503056

Synthesis of highly substituted indolines and indoles via intramolecular [4 + 2] cycloaddition of ynamides and conjugated enynes. Keywords Mesh Terms:

KEYWORDS: Indoles

MESH TERMS: chemical synthesis

Chemical & Substance for Abstract: Synthesis of highly substituted indolines and indoles via intramolecular [4 + 2] cycloaddition of ynamides and conjugated enynes. Information

Substance Name: Indoles

Registry Number: 0

Grant and Affiliation Information for Synthesis of highly substituted indolines and indoles via intramolecular [4 + 2] cycloaddition of ynamides and conjugated enynes.

AFFILIATION: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: GM 28273

ACRONYM: GM

MEDLINETA: J Am Chem Soc

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• Synthesis of highly substituted indolines and indoles via intramolecular [4 + 2] cycloaddition of ynamides and conjugated enynes.