Functionalized 4-Hydroxy Coumarins: Novel Synthesis, Crystal Structure and DFT Calculations

A novel short-step methodology for the synthesis in good yields of functionalized coumarins has been developed starting from an activated precursor, the N-hydroxysuccinimide ester of O-acetylsalicylic acid. The procedure is based on a tandem C-acylation-cyclization process under mild reaction condit...

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Autores principales: Stefanou, Valentina, Matiadis, Dimitris, Melagraki, Georgia, Afantitis, Antreas, Athanasellis, Giorgos, Igglessi-Markopoulou, Olga, McKee, Vickie, Markopoulos, John
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2011
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6259271/
https://www.ncbi.nlm.nih.gov/pubmed/21217604
http://dx.doi.org/10.3390/molecules16010384
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author Stefanou, Valentina
Matiadis, Dimitris
Melagraki, Georgia
Afantitis, Antreas
Athanasellis, Giorgos
Igglessi-Markopoulou, Olga
McKee, Vickie
Markopoulos, John
author_facet Stefanou, Valentina
Matiadis, Dimitris
Melagraki, Georgia
Afantitis, Antreas
Athanasellis, Giorgos
Igglessi-Markopoulou, Olga
McKee, Vickie
Markopoulos, John
author_sort Stefanou, Valentina
collection PubMed
description A novel short-step methodology for the synthesis in good yields of functionalized coumarins has been developed starting from an activated precursor, the N-hydroxysuccinimide ester of O-acetylsalicylic acid. The procedure is based on a tandem C-acylation-cyclization process under mild reaction conditions. The structure of 3-methoxycarbonyl-4-hydroxy coumarin has been established by X-ray diffraction analysis and its geometry was compared with optimized parameters by means of DFT calculations.
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spelling pubmed-62592712018-12-07 Functionalized 4-Hydroxy Coumarins: Novel Synthesis, Crystal Structure and DFT Calculations Stefanou, Valentina Matiadis, Dimitris Melagraki, Georgia Afantitis, Antreas Athanasellis, Giorgos Igglessi-Markopoulou, Olga McKee, Vickie Markopoulos, John Molecules Article A novel short-step methodology for the synthesis in good yields of functionalized coumarins has been developed starting from an activated precursor, the N-hydroxysuccinimide ester of O-acetylsalicylic acid. The procedure is based on a tandem C-acylation-cyclization process under mild reaction conditions. The structure of 3-methoxycarbonyl-4-hydroxy coumarin has been established by X-ray diffraction analysis and its geometry was compared with optimized parameters by means of DFT calculations. MDPI 2011-01-07 /pmc/articles/PMC6259271/ /pubmed/21217604 http://dx.doi.org/10.3390/molecules16010384 Text en © 2011 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 license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Stefanou, Valentina
Matiadis, Dimitris
Melagraki, Georgia
Afantitis, Antreas
Athanasellis, Giorgos
Igglessi-Markopoulou, Olga
McKee, Vickie
Markopoulos, John
Functionalized 4-Hydroxy Coumarins: Novel Synthesis, Crystal Structure and DFT Calculations
title Functionalized 4-Hydroxy Coumarins: Novel Synthesis, Crystal Structure and DFT Calculations
title_full Functionalized 4-Hydroxy Coumarins: Novel Synthesis, Crystal Structure and DFT Calculations
title_fullStr Functionalized 4-Hydroxy Coumarins: Novel Synthesis, Crystal Structure and DFT Calculations
title_full_unstemmed Functionalized 4-Hydroxy Coumarins: Novel Synthesis, Crystal Structure and DFT Calculations
title_short Functionalized 4-Hydroxy Coumarins: Novel Synthesis, Crystal Structure and DFT Calculations
title_sort functionalized 4-hydroxy coumarins: novel synthesis, crystal structure and dft calculations
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6259271/
https://www.ncbi.nlm.nih.gov/pubmed/21217604
http://dx.doi.org/10.3390/molecules16010384
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