Issue 10, 2017

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
18 Apr. 2017
Accepted
04 Aug. 2017
First published
08 Aug. 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 6911-6917

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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