Azaheterocycles Made Easy

  • Author: Asian Journal of Organic Chemistry
  • Published Date: 15 August 2014
  • Source / Publisher: Asian Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Azaheterocycles Made Easy

Azaheterocycles are a highly important class of compounds due to their biological activities and pharmaceutical applications. In particular, dihydroazepines, dihydropyrroles, and pyrroles are constituents of a valuable privileged structure in organic chemistry. 

Phil Ho Lee and co-workers from Kangwon National University, Republic of Korea, made these compounds by an overall aza-[4+3] annulation reaction through sequential [3+2]/[2+1] cycloadditions-aza-Cope rearrangement. Aza-[3+2] annulation was achieved through [3+2]/[2+1]-aza-Cope rearrangement-1,3-migration or [3+2]/[2+1]-Clock rearrangement. This method provides a straightforward synthetic route from simple triazoles to dihydroazepines and dihydropyrroles with liberation of N2 as the single byproduct. 

This procedure was successfully applied to a one-pot process starting from terminal alkynes, azides, and dienes. A wide range of substrates in terminal alkynes and 1,3-dienes are selectively annulated with excellent functional group tolerance, thus opening a new and practical avenue for the production of azaheterocycles.

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