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First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones

Aryl and hetaryl thiochalcones react smoothly with 1,4-quinones in THF solution at 60 °C yielding the corresponding fused 4H-thiopyrans after spontaneous dehydrogenation of the initially formed [4 + 2] cycloadducts. In general, the yields of the isolated products were high. With 5-chloro-10-hydroxy-...

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Autores principales: Mlostoń, Grzegorz, Urbaniak, Katarzyna, Urbaniak, Paweł, Marko, Anna, Linden, Anthony, Heimgartner, Heinz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6071716/
https://www.ncbi.nlm.nih.gov/pubmed/30112087
http://dx.doi.org/10.3762/bjoc.14.156
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author Mlostoń, Grzegorz
Urbaniak, Katarzyna
Urbaniak, Paweł
Marko, Anna
Linden, Anthony
Heimgartner, Heinz
author_facet Mlostoń, Grzegorz
Urbaniak, Katarzyna
Urbaniak, Paweł
Marko, Anna
Linden, Anthony
Heimgartner, Heinz
author_sort Mlostoń, Grzegorz
collection PubMed
description Aryl and hetaryl thiochalcones react smoothly with 1,4-quinones in THF solution at 60 °C yielding the corresponding fused 4H-thiopyrans after spontaneous dehydrogenation of the initially formed [4 + 2] cycloadducts. In general, the yields of the isolated products were high. With 5-chloro-10-hydroxy-1,4-anthraquinone, the thia-Diels–Alder reaction occurred with complete regioselectivity. In the case of the reaction of vitamin K(3) (menadione) with diphenylthiochalcone, the initial cycloadduct was isolated in 37% yield.
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spelling pubmed-60717162018-08-15 First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones Mlostoń, Grzegorz Urbaniak, Katarzyna Urbaniak, Paweł Marko, Anna Linden, Anthony Heimgartner, Heinz Beilstein J Org Chem Full Research Paper Aryl and hetaryl thiochalcones react smoothly with 1,4-quinones in THF solution at 60 °C yielding the corresponding fused 4H-thiopyrans after spontaneous dehydrogenation of the initially formed [4 + 2] cycloadducts. In general, the yields of the isolated products were high. With 5-chloro-10-hydroxy-1,4-anthraquinone, the thia-Diels–Alder reaction occurred with complete regioselectivity. In the case of the reaction of vitamin K(3) (menadione) with diphenylthiochalcone, the initial cycloadduct was isolated in 37% yield. Beilstein-Institut 2018-07-19 /pmc/articles/PMC6071716/ /pubmed/30112087 http://dx.doi.org/10.3762/bjoc.14.156 Text en Copyright © 2018, Mlostoń et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Mlostoń, Grzegorz
Urbaniak, Katarzyna
Urbaniak, Paweł
Marko, Anna
Linden, Anthony
Heimgartner, Heinz
First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones
title First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones
title_full First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones
title_fullStr First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones
title_full_unstemmed First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones
title_short First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones
title_sort first thia-diels–alder reactions of thiochalcones with 1,4-quinones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6071716/
https://www.ncbi.nlm.nih.gov/pubmed/30112087
http://dx.doi.org/10.3762/bjoc.14.156
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