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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2015
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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. |
format | Online Article Text |
id | pubmed-4362022 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
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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