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Intramolecular reaction
About: Intramolecular reaction is a research topic. Over the lifetime, 5015 publications have been published within this topic receiving 138213 citations.
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TL;DR: This novel amidation reaction involves a catalytic protocol using copper(II) sulfate-pentahydrate and 1,10-phenanthroline to direct the sp-C-N bond formation, leading to a structurally diverse array of ynamide including macrocyclic ynamides via an intramolecular amidation.
Abstract: A general and efficient method for the coupling of a wide range of amides with alkynyl bromides is described here. This novel amidation reaction involves a catalytic protocol using copper(II) sulfate-pentahydrate and 1,10-phenanthroline to direct the sp-C−N bond formation, leading to a structurally diverse array of ynamides including macrocyclic ynamides via an intramolecular amidation. Given the surging interest in ynamide chemistry, this atom economical synthesis of ynamides should invoke further attention from the synthetic organic community.
166 citations
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165 citations
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TL;DR: A novel Pd-catalyzed intramolecular allylic alkylation of indoles allows THBCs and THGCs to be effectively synthesized in high yields and excellent enantiomeric excesses.
Abstract: A novel Pd-catalyzed intramolecular allylic alkylation of indoles allows THBCs and THGCs to be effectively synthesized in high yields and excellent enantiomeric excesses (ee up to 97%).
165 citations
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TL;DR: In the presence of n -Bu4NCl, DMF and an appropriate base (Na2CO3, NaOAc or Et3N) cyclize nitrogen-containing o -iodoaryl alkenes to indoles, indolines,3 oxindoles, quinolines and isoquinolines.
163 citations
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TL;DR: 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.
Abstract: 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 2π components in the cycloaddition, providing access to indolines with carbon substituents at the C-7 position. Enynamides serve as 4π 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 °C in toluene or 2,2,2-trifluoroethanol and in some cases can be achieved at 0 °C to room temperature in the presence of Lewis acids such as Me2AlCl.
163 citations