Hetero-Diels–Alder reactions of hetaryl thiochalcones with acetylenic dienophiles

Mlostoń, Grzegorz; Grzelak, Paulina; Heimgartner, Heinz

doi:10.1080/17415993.2016.1230857

Cited by 20 publications

(16 citation statements)

References 29 publications

(18 reference statements)

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“…5-Chloro-10-hydroxy-1,4-anthraquinone ( 2d ) was obtained by treatment of quinizarine with thionyl chloride according to the protocol described in [27]. Thiochalcones 1a – d were prepared according to our protocol reported in an earlier publication [16]. …”

Section: Methodsmentioning

confidence: 99%

“…Despite the fact that thiochalcones exist in solution as mixtures of dimers [15–16], they enter into cycloaddition reactions not only as heterodienes [17–19], but also as heterodipolarophiles [15]. In two recent publications we reported new thia-Diels–Alder reactions of aryl, hetaryl and ferrocenyl-substituted thiochalcones with acetylenic dienophiles, which lead to the corresponding 4 H -thiopyrans in a regioselective manner [16,20].…”

Section: Introductionmentioning

confidence: 99%

“…In two recent publications we reported new thia-Diels–Alder reactions of aryl, hetaryl and ferrocenyl-substituted thiochalcones with acetylenic dienophiles, which lead to the corresponding 4 H -thiopyrans in a regioselective manner [16,20]. …”

Section: Introductionmentioning

confidence: 99%

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

Mlostoń

Urbaniak

et al. 2018

Beilstein J. Org. Chem.

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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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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Mlostoń

Urbaniak

et al. 2018

Beilstein J. Org. Chem.

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“…In a recent publication we reported that acetylenic dipolarophiles react with thiochalcones 2 (Ar = Aryl or Hetaryl) yielding 4H-thiopyrans 3 in good to excellent yields, and in the case of methyl propiolate the reaction occurred with complete regioselectivity [6] (Scheme 1). Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

“…Scheme 1. Preparation of thiochalcones 2 and their regioselective hetero-Diels-Alder reactions with methyl propiolate [6].…”

Section: Introductionmentioning

confidence: 99%

First synthesis of ferrocenyl-substituted thiochalcones and their [4+2]-cycloadditions with acetylenic dienophiles

Mlostoń

Hamera-Fałdyga

Heimgartner

2018

Journal of Sulfur Chemistry

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Ferrocenyl methyl ketone reacts with aromatic aldehydes yielding 1-ferrocenyl-3-aryl-propenones (chalcones), which upon treatment with Lawesson's reagent (LR) are converted to the corresponding thiochalcones. The latter enter the thia-Diels-Alder reaction with acetylenic dienophiles (DMAD and methyl propiolate) to give ferrocenyl-substituted 4H-thiopyrans. In the case of methyl propiolate, the formation of the six-membered ring occurs with complete regioselectivity.

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Chalcones, a Privileged Scaffold: Highly Versatile Molecules in [4+2] Cycloadditions

Mastachi-Loza

Ramírez-Candelero²,

Benítez‐Puebla

et al. 2022

Chemistry An Asian Journal

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Chalcones are aromatic ketones found in nature as the central core of many biological compounds. They have a wide range of biological activity and are biogenetic precursors of other important molecules such as flavonoids. Their pharmacological relevance makes them a privileged scaffold, advantageous for seeking alternative therapies in medicinal chemistry. Due to their structural diversity and ease of synthesis, they are often employed as building blocks for chemical transformations. Chalcones have a carbonyl conjugated system with two electrophilic centers that are commonly used for nucleophilic additions, as described in numerous articles. They can also participate in Diels-Alder reactions, which are [4 + 2] cycloadditions between a diene and a dienophile. This microreview presents a chronological survey of studies on chalcones as dienes and dienophiles in Diels-Alder cycloadditions. Although these reactions occur in nature, isolation of chalcones from plants yields very small quantities. Contrarily, synthesis leads to large quantities at a low cost. Hence, novel methodologies have been developed for [4 + 2] cycloadditions, with chalcones serving as a 2π or 4π electron system.

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Hetero-Diels–Alder reactions of hetaryl thiochalcones with acetylenic dienophiles

Cited by 20 publications

References 29 publications

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

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

First synthesis of ferrocenyl-substituted thiochalcones and their [4+2]-cycloadditions with acetylenic dienophiles

Chalcones, a Privileged Scaffold: Highly Versatile Molecules in [4+2] Cycloadditions

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