Projects per year
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.
Original language | English |
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Pages (from-to) | 6911-6917 |
Journal | Chemical Science |
Volume | 8 |
Issue number | 10 |
Early online date | 8 Aug 2017 |
DOIs | |
Publication status | Published - 1 Oct 2017 |
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Dive into the research topics of 'A new route to N-aromatic heterocycles from the hydrogenation of diesters in the presence of anilines'. Together they form a unique fingerprint.Projects
- 2 Finished
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Clean catalysis for sustainable develop: Clean catalysis for sustainable development
Cole-Hamilton, D. J. (PI)
1/11/12 → 31/10/17
Project: Standard
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Clean catalysis for sustainable develop: Clean catalysis for sustainable development
Kamer, P. C. J. (PI)
1/11/12 → 31/10/17
Project: Standard