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Solvent-Free Synthesis of 2,5-Bis((dimethylamino)methylene)cyclopentanone
Available protocols for the synthesis of ketocyanine dyes precursor 2,5-bis((dimethylamino)methylene)cyclopentanone are not straightforward and the reported yields are low to moderate. The important feature in the synthesis of this product through organocatalyzed condensation of cyclopentanone and N...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6789771/ https://www.ncbi.nlm.nih.gov/pubmed/31409032 http://dx.doi.org/10.3390/mps2030069 |
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author | S. Martins, Inês A. S. Coelho, Jaime |
author_facet | S. Martins, Inês A. S. Coelho, Jaime |
author_sort | S. Martins, Inês |
collection | PubMed |
description | Available protocols for the synthesis of ketocyanine dyes precursor 2,5-bis((dimethylamino)methylene)cyclopentanone are not straightforward and the reported yields are low to moderate. The important feature in the synthesis of this product through organocatalyzed condensation of cyclopentanone and N,N-Dimethylformamide dimethyl acetal is the removal of methanol produced during the reaction. By studying the reaction profile, in particular the selectivity for the formation of mono- and bis-condensation products, a high yield of the desired product can be obtained through an operationally simple and solvent-free protocol. |
format | Online Article Text |
id | pubmed-6789771 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-67897712019-10-16 Solvent-Free Synthesis of 2,5-Bis((dimethylamino)methylene)cyclopentanone S. Martins, Inês A. S. Coelho, Jaime Methods Protoc Protocol Available protocols for the synthesis of ketocyanine dyes precursor 2,5-bis((dimethylamino)methylene)cyclopentanone are not straightforward and the reported yields are low to moderate. The important feature in the synthesis of this product through organocatalyzed condensation of cyclopentanone and N,N-Dimethylformamide dimethyl acetal is the removal of methanol produced during the reaction. By studying the reaction profile, in particular the selectivity for the formation of mono- and bis-condensation products, a high yield of the desired product can be obtained through an operationally simple and solvent-free protocol. MDPI 2019-08-12 /pmc/articles/PMC6789771/ /pubmed/31409032 http://dx.doi.org/10.3390/mps2030069 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Protocol S. Martins, Inês A. S. Coelho, Jaime Solvent-Free Synthesis of 2,5-Bis((dimethylamino)methylene)cyclopentanone |
title | Solvent-Free Synthesis of 2,5-Bis((dimethylamino)methylene)cyclopentanone |
title_full | Solvent-Free Synthesis of 2,5-Bis((dimethylamino)methylene)cyclopentanone |
title_fullStr | Solvent-Free Synthesis of 2,5-Bis((dimethylamino)methylene)cyclopentanone |
title_full_unstemmed | Solvent-Free Synthesis of 2,5-Bis((dimethylamino)methylene)cyclopentanone |
title_short | Solvent-Free Synthesis of 2,5-Bis((dimethylamino)methylene)cyclopentanone |
title_sort | solvent-free synthesis of 2,5-bis((dimethylamino)methylene)cyclopentanone |
topic | Protocol |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6789771/ https://www.ncbi.nlm.nih.gov/pubmed/31409032 http://dx.doi.org/10.3390/mps2030069 |
work_keys_str_mv | AT smartinsines solventfreesynthesisof25bisdimethylaminomethylenecyclopentanone AT ascoelhojaime solventfreesynthesisof25bisdimethylaminomethylenecyclopentanone |