4.8 Article

Short and Modular Synthesis of Substituted 2-Aminopyrroles

Journal

ORGANIC LETTERS
Volume 23, Issue 10, Pages 4078-4082

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01345

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Funding

  1. Spanish Ministries of Science, Innovation and Universities (MICINN)
  2. Agencia Estatal de Investigacion (AEI)
  3. European Regional Development Funds (ERDF) [PGC2018-094503-B-C21]
  4. Norwegian PhD School of Pharmacy

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A simple and metal-free domino methodology was used to synthesize various 2-aminopyrroles from alkynyl vinyl hydrazides, involving a novel rearrangement and cyclization reaction. This approach allowed the preparation of 2-amino-pyrroles with diverse substituents.
We herein describe a simple and metal-free domino methodology to synthesize 2-aminopyrroles from alkynyl vinyl hydrazides. The domino reaction involves a novel propargylic 3,4-diaza-Cope rearrangement and a tandem isomerization/5-exo-dig N-cyclization reaction. By using this approach, a number of 2-amino-pyrroles with diverse substituents have been prepared.

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