Nitrogen-Containing Polycycles from Furans

  • Author: Kevin Jones
  • Published Date: 03 July 2013
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
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Georgios Vassilkogiannakis and co-workers from the University of Crete, Greece, have reported an interesting method for the formation nitrogen-bearing polycycles. The approach involves photooxidation of furan derivative 1 to generate a 1,4-dielectrophile 2 which reacts with an amine nucleophile to give pyrolidinone 3. Addition of a Brønsted or Lewis acid generates N-acyl iminium ion 4, which undergoes a Pictet–Spengler-type reaction with the pendent aromatic group on the amine to give the final product (see scheme; a more detailed description of the proposed mechanism is given on the first page of the manuscript).

The final Pictet--Spengler step could be achieved with a variety of pendent aromatics although unactivated groups (such as 8) required the use of a stronger Lewis acid (AlCl3). In addition, Mono-, di, and tri-substituted furans were also tolerated, but only activated aromatics would undergo the final cyclization step in the case of the di- and tri-substituted examples.

The reactions are performed in one-pot by sequential addition of reagents and lead to a rapid increase in chemical complexity. Additionally, as many of the products possess the core structure of the erythrina alkaloids this may become a useful synthetic method

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Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH