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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...

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Detalles Bibliográficos
Autores principales: S. Martins, Inês, A. S. Coelho, Jaime
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
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.
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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
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