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Green synthesis, crystal structure, and antifungal activities of (E)-4-arylidene-5-oxotetrahydrofuran

A series of γ-lactone derivatives (E)-4-arylidene-5-oxotetrahydrofuran derivatives were synthesized via a tandem Passerini 3CC/S(N) cyclization microwave-assisted one-pot method efficiently starting from Baylis Hillman acids, aryl glyoxals and isocyanides, and using ionic liquid as reaction medium....

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Autores principales: Dong, Yun, Kong, Ling-Qi, Chen, Qin-Hua, Li, Bin, Zeng, Xiao-Hua, Ke, Li-Na, Wang, Hong-Mei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9500531/
https://www.ncbi.nlm.nih.gov/pubmed/36157041
http://dx.doi.org/10.3389/fchem.2022.997095
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author Dong, Yun
Kong, Ling-Qi
Chen, Qin-Hua
Li, Bin
Zeng, Xiao-Hua
Ke, Li-Na
Wang, Hong-Mei
author_facet Dong, Yun
Kong, Ling-Qi
Chen, Qin-Hua
Li, Bin
Zeng, Xiao-Hua
Ke, Li-Na
Wang, Hong-Mei
author_sort Dong, Yun
collection PubMed
description A series of γ-lactone derivatives (E)-4-arylidene-5-oxotetrahydrofuran derivatives were synthesized via a tandem Passerini 3CC/S(N) cyclization microwave-assisted one-pot method efficiently starting from Baylis Hillman acids, aryl glyoxals and isocyanides, and using ionic liquid as reaction medium. The products were characterized by hydrogen nuclear magnetic resonance spectroscopy ((1)H-NMR), carbon nuclear magnetic resonance spectroscopy ((13)C-NMR). Single crystal X-ray analysis of the compound RPDFB clearly confirmed its assigned chemical structures. Meanwhile, the effects of four compounds (RPDFB, RPDFC, RPDFI, RPDFJ) on the growth inhibition activity of Gibberella zeae were detected, and found that the compound RPDFB has significant growth inhibition activity to Gibberella zeae.
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spelling pubmed-95005312022-09-24 Green synthesis, crystal structure, and antifungal activities of (E)-4-arylidene-5-oxotetrahydrofuran Dong, Yun Kong, Ling-Qi Chen, Qin-Hua Li, Bin Zeng, Xiao-Hua Ke, Li-Na Wang, Hong-Mei Front Chem Chemistry A series of γ-lactone derivatives (E)-4-arylidene-5-oxotetrahydrofuran derivatives were synthesized via a tandem Passerini 3CC/S(N) cyclization microwave-assisted one-pot method efficiently starting from Baylis Hillman acids, aryl glyoxals and isocyanides, and using ionic liquid as reaction medium. The products were characterized by hydrogen nuclear magnetic resonance spectroscopy ((1)H-NMR), carbon nuclear magnetic resonance spectroscopy ((13)C-NMR). Single crystal X-ray analysis of the compound RPDFB clearly confirmed its assigned chemical structures. Meanwhile, the effects of four compounds (RPDFB, RPDFC, RPDFI, RPDFJ) on the growth inhibition activity of Gibberella zeae were detected, and found that the compound RPDFB has significant growth inhibition activity to Gibberella zeae. Frontiers Media S.A. 2022-09-09 /pmc/articles/PMC9500531/ /pubmed/36157041 http://dx.doi.org/10.3389/fchem.2022.997095 Text en Copyright © 2022 Dong, Kong, Chen, Li, Zeng, Ke and Wang. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Dong, Yun
Kong, Ling-Qi
Chen, Qin-Hua
Li, Bin
Zeng, Xiao-Hua
Ke, Li-Na
Wang, Hong-Mei
Green synthesis, crystal structure, and antifungal activities of (E)-4-arylidene-5-oxotetrahydrofuran
title Green synthesis, crystal structure, and antifungal activities of (E)-4-arylidene-5-oxotetrahydrofuran
title_full Green synthesis, crystal structure, and antifungal activities of (E)-4-arylidene-5-oxotetrahydrofuran
title_fullStr Green synthesis, crystal structure, and antifungal activities of (E)-4-arylidene-5-oxotetrahydrofuran
title_full_unstemmed Green synthesis, crystal structure, and antifungal activities of (E)-4-arylidene-5-oxotetrahydrofuran
title_short Green synthesis, crystal structure, and antifungal activities of (E)-4-arylidene-5-oxotetrahydrofuran
title_sort green synthesis, crystal structure, and antifungal activities of (e)-4-arylidene-5-oxotetrahydrofuran
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9500531/
https://www.ncbi.nlm.nih.gov/pubmed/36157041
http://dx.doi.org/10.3389/fchem.2022.997095
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