2-(1-Hydroxypropyn-2-yl)-1-vinylpyrroles: the first successful Favorsky ethynylation of pyrrolecarbaldehydes

1-Vinylpyrrole-2-carbaldehydes react with acetylene at atmospheric pressure in a NaOH/EtOH/DMSO system at 7–10 °C to afford 2-(1-hydroxypropyn-2-yl)-1-vinylpyrroles in 53–94% yield. Thus, the first base-mediated direct ethynylation of pyrrolecarbaldehydes with free acetylene under modified condition...

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Autores principales: Ivanov, A V, Shcherbakova, V S, Ushakov, I A, Sobenina, L N, Petrova, O V, Mikhaleva, A I, Trofimov, B A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4362022/
https://www.ncbi.nlm.nih.gov/pubmed/25815074
http://dx.doi.org/10.3762/bjoc.11.25
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author Ivanov, A V
Shcherbakova, V S
Ushakov, I A
Sobenina, L N
Petrova, O V
Mikhaleva, A I
Trofimov, B A
author_facet Ivanov, A V
Shcherbakova, V S
Ushakov, I A
Sobenina, L N
Petrova, O V
Mikhaleva, A I
Trofimov, B A
author_sort Ivanov, A V
collection PubMed
description 1-Vinylpyrrole-2-carbaldehydes react with acetylene at atmospheric pressure in a NaOH/EtOH/DMSO system at 7–10 °C to afford 2-(1-hydroxypropyn-2-yl)-1-vinylpyrroles in 53–94% yield. Thus, the first base-mediated direct ethynylation of pyrrolecarbaldehydes with free acetylene under modified conditions of the Favorsky reaction has been implemented to pave an expedient route to important biomolecules containing a pyrrole ring.
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spelling pubmed-43620222015-03-26 2-(1-Hydroxypropyn-2-yl)-1-vinylpyrroles: the first successful Favorsky ethynylation of pyrrolecarbaldehydes Ivanov, A V Shcherbakova, V S Ushakov, I A Sobenina, L N Petrova, O V Mikhaleva, A I Trofimov, B A Beilstein J Org Chem Full Research Paper 1-Vinylpyrrole-2-carbaldehydes react with acetylene at atmospheric pressure in a NaOH/EtOH/DMSO system at 7–10 °C to afford 2-(1-hydroxypropyn-2-yl)-1-vinylpyrroles in 53–94% yield. Thus, the first base-mediated direct ethynylation of pyrrolecarbaldehydes with free acetylene under modified conditions of the Favorsky reaction has been implemented to pave an expedient route to important biomolecules containing a pyrrole ring. Beilstein-Institut 2015-02-10 /pmc/articles/PMC4362022/ /pubmed/25815074 http://dx.doi.org/10.3762/bjoc.11.25 Text en Copyright © 2015, Ivanov et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Ivanov, A V
Shcherbakova, V S
Ushakov, I A
Sobenina, L N
Petrova, O V
Mikhaleva, A I
Trofimov, B A
2-(1-Hydroxypropyn-2-yl)-1-vinylpyrroles: the first successful Favorsky ethynylation of pyrrolecarbaldehydes
title 2-(1-Hydroxypropyn-2-yl)-1-vinylpyrroles: the first successful Favorsky ethynylation of pyrrolecarbaldehydes
title_full 2-(1-Hydroxypropyn-2-yl)-1-vinylpyrroles: the first successful Favorsky ethynylation of pyrrolecarbaldehydes
title_fullStr 2-(1-Hydroxypropyn-2-yl)-1-vinylpyrroles: the first successful Favorsky ethynylation of pyrrolecarbaldehydes
title_full_unstemmed 2-(1-Hydroxypropyn-2-yl)-1-vinylpyrroles: the first successful Favorsky ethynylation of pyrrolecarbaldehydes
title_short 2-(1-Hydroxypropyn-2-yl)-1-vinylpyrroles: the first successful Favorsky ethynylation of pyrrolecarbaldehydes
title_sort 2-(1-hydroxypropyn-2-yl)-1-vinylpyrroles: the first successful favorsky ethynylation of pyrrolecarbaldehydes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4362022/
https://www.ncbi.nlm.nih.gov/pubmed/25815074
http://dx.doi.org/10.3762/bjoc.11.25
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