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


Mloston, Grzegorz; Urbaniak, Katarzyna; Urbaniak, Pawel; Marko, Anna; Linden, Anthony; Heimgartner, Heinz (2018). First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones. Beilstein Journal of Organic Chemistry, 14:1834-1839.

Abstract

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 K3 (menadione) with diphenylthiochalcone, the initial cycloadduct was isolated in 37% yield.

Abstract

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 K3 (menadione) with diphenylthiochalcone, the initial cycloadduct was isolated in 37% yield.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:Organic Chemistry
Language:English
Date:19 July 2018
Deposited On:26 Jul 2018 15:38
Last Modified:04 Dec 2018 14:52
Publisher:Beilstein-Institut
ISSN:1860-5397
OA Status:Gold
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.3762/bjoc.14.156

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