Synthesis of N-Heterocycles from Propargylamines

  • Author: Chemistry – A European Journal
  • Published Date: 16 February 2020
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Synthesis of N-Heterocycles from Propargylamines

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Highly functionalized pyrrole, pentafulvene, and pyrrolopyridine derivatives are useful compounds in the fields of medicinal and organic materials chemistry. However, synthetic methods for these derivatives are limited and often require starting materials that are difficult to obtain.

Taku Shoji, Shinshu University, Japan, and colleagues have developed a practical synthesis of highly functionalized pyrrole, pentafulvene, and pyrrolopyridine derivatives. The desired compounds are prepared via a [2+2] cycloaddition–retroelectrocyclization (CA–RE) of N-substituted propargylamines with tetracyanoethylene, followed by treatment with silica gel (pictured below). The silica gel mediates the formation of the desired ring from a tetracyanobutadiene intermediate.

The team found that the selectivity for the product of the reaction (i.e. pyrrole, pentafulvene, or pyrrolopyridine) is dependent on the substituent at the nitrogen atom of the propargylamines (see below). The products were prepared in high yields from inexpensive and readily available reagents under mild reaction conditions.




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