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

نویسندگان

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

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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عنوان ژورنال:
  • Chemical science

دوره 8 10  شماره 

صفحات  -

تاریخ انتشار 2017