Synthesis of amides and esters containing furan rings under microwave-assisted conditions

In this work, we present a novel method for the synthesis of ester and amide derivatives containing furan rings (furfural derivatives) under mild synthetic conditions supported by microwave radiation. N-(Furan-2-ylmethyl)furan-2-carboxamide and furan-2-ylmethyl furan-2-carboxylate were produced usin...

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Autores principales:	Janczewski Łukasz, Zieliński Dariusz, Kolesińska Beata
Formato:	article
Lenguaje:	EN
Publicado:	De Gruyter 2021
Materias:	microwave chemistry furfuryl alcohol furoic acid amides coupling reagent Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/6319b559d26a48999e94ee085ce24987
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spelling	oai:doaj.org-article:6319b559d26a48999e94ee085ce249872021-12-05T14:10:43ZSynthesis of amides and esters containing furan rings under microwave-assisted conditions2391-542010.1515/chem-2021-0034https://doaj.org/article/6319b559d26a48999e94ee085ce249872021-03-01T00:00:00Zhttps://doi.org/10.1515/chem-2021-0034https://doaj.org/toc/2391-5420In this work, we present a novel method for the synthesis of ester and amide derivatives containing furan rings (furfural derivatives) under mild synthetic conditions supported by microwave radiation. N-(Furan-2-ylmethyl)furan-2-carboxamide and furan-2-ylmethyl furan-2-carboxylate were produced using 2-furoic acid, furfurylamine, and furfuryl alcohol. The reactions were carried out in a microwave reactor in the presence of effective coupling reagents: DMT/NMM/TsO− or EDC. The reaction time, the solvent, and the amounts of the substrates were optimized. After crystallization or flash chromatography, the final compounds were isolated with good or very good yields. Our method allows for the synthesis of N-blocked amides using N-blocked amino acids (Boc, Cbz, Fmoc) and amine. As well as compounds with a monoamide and ester moiety, products with diamides and diester bonds (N,N-bis(furan-2-ylmethyl)furan-2,5-dicarboxamide, bis(furan-2-ylmethyl) furan-2,5-dicarboxylate, and furan-3,4-diylbis(methylene) bis(furan-2-carboxylate)) were synthesized with moderate yields in the presence of DMT/NMM/TsO– or EDC, using 2,5-furandicarboxylic acid and 3,4-bis(hydroxymethyl)furan as substrates.Janczewski ŁukaszZieliński DariuszKolesińska BeataDe Gruyterarticlemicrowave chemistryfurfuryl alcoholfuroic acidamidescoupling reagentChemistryQD1-999ENOpen Chemistry, Vol 19, Iss 1, Pp 265-280 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	microwave chemistry furfuryl alcohol furoic acid amides coupling reagent Chemistry QD1-999
spellingShingle	microwave chemistry furfuryl alcohol furoic acid amides coupling reagent Chemistry QD1-999 Janczewski Łukasz Zieliński Dariusz Kolesińska Beata Synthesis of amides and esters containing furan rings under microwave-assisted conditions
description	In this work, we present a novel method for the synthesis of ester and amide derivatives containing furan rings (furfural derivatives) under mild synthetic conditions supported by microwave radiation. N-(Furan-2-ylmethyl)furan-2-carboxamide and furan-2-ylmethyl furan-2-carboxylate were produced using 2-furoic acid, furfurylamine, and furfuryl alcohol. The reactions were carried out in a microwave reactor in the presence of effective coupling reagents: DMT/NMM/TsO− or EDC. The reaction time, the solvent, and the amounts of the substrates were optimized. After crystallization or flash chromatography, the final compounds were isolated with good or very good yields. Our method allows for the synthesis of N-blocked amides using N-blocked amino acids (Boc, Cbz, Fmoc) and amine. As well as compounds with a monoamide and ester moiety, products with diamides and diester bonds (N,N-bis(furan-2-ylmethyl)furan-2,5-dicarboxamide, bis(furan-2-ylmethyl) furan-2,5-dicarboxylate, and furan-3,4-diylbis(methylene) bis(furan-2-carboxylate)) were synthesized with moderate yields in the presence of DMT/NMM/TsO– or EDC, using 2,5-furandicarboxylic acid and 3,4-bis(hydroxymethyl)furan as substrates.
format	article
author	Janczewski Łukasz Zieliński Dariusz Kolesińska Beata
author_facet	Janczewski Łukasz Zieliński Dariusz Kolesińska Beata
author_sort	Janczewski Łukasz
title	Synthesis of amides and esters containing furan rings under microwave-assisted conditions
title_short	Synthesis of amides and esters containing furan rings under microwave-assisted conditions
title_full	Synthesis of amides and esters containing furan rings under microwave-assisted conditions
title_fullStr	Synthesis of amides and esters containing furan rings under microwave-assisted conditions
title_full_unstemmed	Synthesis of amides and esters containing furan rings under microwave-assisted conditions
title_sort	synthesis of amides and esters containing furan rings under microwave-assisted conditions
publisher	De Gruyter
publishDate	2021
url	https://doaj.org/article/6319b559d26a48999e94ee085ce24987
work_keys_str_mv	AT janczewskiłukasz synthesisofamidesandesterscontainingfuranringsundermicrowaveassistedconditions AT zielinskidariusz synthesisofamidesandesterscontainingfuranringsundermicrowaveassistedconditions AT kolesinskabeata synthesisofamidesandesterscontainingfuranringsundermicrowaveassistedconditions
_version_	1718371788610600960

Synthesis of amides and esters containing furan rings under microwave-assisted conditions

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