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Issue 10, 2017
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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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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.

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

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Publication details

The article was received on 18 Apr 2017, accepted on 04 Aug 2017 and first published on 08 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC01718A
Citation: Chem. Sci., 2017,8, 6911-6917
  • Open access: Creative Commons BY license
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    A new route to N-aromatic heterocycles from the hydrogenation of diesters in the presence of anilines

    Y. Shi, P. C. J. Kamer, D. J. Cole-Hamilton, M. Harvie, E. F. Baxter, K. J. C. Lim and P. Pogorzelec, Chem. Sci., 2017, 8, 6911
    DOI: 10.1039/C7SC01718A

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