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A new route to N-aromatic heterocycles from the hydrogenation of diesters in the presence of anilines

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Yiping Shi, Paul C. J. Kamer, David J. Cole-Hamilton, Michelle Harvie, Emma F. Baxter, Kate J. C. Lim, Peter Pogorzelec

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Abstract

The hydrogenation of dicarboxylic acids and their esters in the presence of anilines provides a new synthesis of heterocycles. [Ru(acac)3] and 1,1,1-tris(diphenylphosphinomethyl)ethane (triphos) gave good to excellent yields of the cyclic amines at 220 °C. When aqueous ammonia was used with dimethyl 1,6-hexadienoic acid, ε-caprolactam was obtained in good yield. A side reaction involving alkylation of the amine by methanol was suppressed by using diesters derived from longer chain and branched alcohols. Hydrogenation of optically pure diesters (dimethyl (R)-2-methylbutanedioate and dimethyl (S)-2- methylbutanedioate) with aniline afforded racemic 3-methyl-1-phenylpyrrolidine in 78 % yield.
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Original languageEnglish
Pages (from-to)6911-6917
JournalChemical Science
Volume8
Issue number10
Early online date8 Aug 2017
DOIs
StatePublished - 1 Oct 2017

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