Short and Modular Synthesis of Substituted 2-Aminopyrroles

Raquel Diana-Rivero; Beate Halsvik; Fernando García Tellado; David Tejedor

doi:10.1021/acs.orglett.1c01345

Short and Modular Synthesis of Substituted 2-Aminopyrroles

Org Lett. 2021 May 21;23(10):4078-4082. doi: 10.1021/acs.orglett.1c01345. Epub 2021 Apr 30.

Authors

Raquel Diana-Rivero^{1

2}, Beate Halsvik³, Fernando García Tellado¹, David Tejedor¹

Affiliations

¹ Instituto de Productos Naturales y Agrobiología, CSIC, Astrofísico Francisco Sánchez 3, 38206 La Laguna, Tenerife, Spain.
² Doctoral and Postgraduate School, Universidad de La Laguna, Santa Cruz de Tenerife, Spain.
³ Department of Chemistry, University of Bergen, Allégaten 41, NO-5007 Bergen, Norway.

Abstract

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-aminopyrroles with diverse substituents have been prepared.