Dearomatizative and Decarboxylative Reaction Cascade in the Aminocatalytic Synthesis of 3,4‐Dihydrocoumarins

Bojanowski, Jan; Skrzyńska, Anna; Albrecht, Anna

doi:10.1002/ajoc.201900222

Cited by 16 publications

(6 citation statements)

References 60 publications

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“…Although naturally occurring dihydrocoumarin concentrations are limited in plants, advances in organic synthesis technology have enabled the development of multiple methods for dihydrocoumarin production, including microbial biocatalysis from coumarin (Häser et al, 2006) and organic synthesis (Bojanowski et al, 2019;Kelley et al, 2020). It is therefore not difficult to obtain dihydrocoumarin in large quantities.…”

Section: Discussionmentioning

confidence: 99%

The potential of Myosoton aquaticum extracts and compounds to control barnyardgrass (Echinochloa crus‐galli)

et al. 2021

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Although cover crops are widely used for weed suppression in the agroecosystem, little research is available regarding the possibility that the decomposed weed solution may control weeds. In this study, we tested the allelopathic effect of decomposed weed solution on barnyardgrass (Echinochloa crus-galli). In two separate tests, we found that the solution of decomposed Myosoton aquaticum completely suppressed the germination of barnyardgrass seeds at a concentration of 20 g l-1. We then isolated and identified the predominant inhibitory substance in the decomposed M. aquaticum solution. The solution was subjected to organic solvent extraction and then separated on a silica gel column before the final identification of its components by high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/ MS). Dihydrocoumarin was isolated from the M2 and M3 fractions using a bioassayguided method and was found to be the most active of eleven candidate allelochemical compounds. Dihydrocoumarin is typically used as a food additive. In this study, barnyardgrass germination was completely inhibited when treated with dihydrocoumarin at 1 g l-1, and its root and shoot growth were significantly inhibited at an application rate of 0.005 g l-1. Dihydrocoumarin showed highly efficient inhibition of root and shoot growth in barnyardgrass at low concentrations compared with coumarin.These findings show that weeds may be used as cover crops to provide allelochemicals for weed suppression and that dihydrocoumarin has the potential to be used as a bioherbicide.

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Section: Discussionmentioning

confidence: 99%

The potential of Myosoton aquaticum extracts and compounds to control barnyardgrass (Echinochloa crus‐galli)

et al. 2021

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“…A similar approach was exploited shortly after by the group of A. Albrecht [15] . In this study, the authors developed a dearomative and decarboxylative cycloaddition reaction between γ‐aryl‐3‐furfurals 15 and coumarin‐3‐carboxylic acids 20 in the presence of 20 mol% of C1 .…”

Section: Organocatalytic [4+2] Cycloadditions Involving Heterocyclic ...mentioning

confidence: 99%

Shaping Chirality via Stereoselective, Organocatalytic [4+2] Cycloadditions involving Heterocyclic ortho‐Quinodimethanes

Marcantonio,

Curti

2024

Chemistry A European J

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Polycyclic compounds bearing a complex heterocyclic core such as an aromatic heterocycle “fused” with one or more functionalized rings, are widespread leading molecules in the domain of synthetic organic chemistry and pharmaceuticals. Although many synthetic methodologies have been devised to access achiral, fused heteroaromatic scaffolds, or related chiral variants adorned with out‐of‐cycle stereogenic elements, equally efficient strategies to afford chiral heterocycles featuring in‐cycle stereocenters, exist to a lesser extent and presently represent a growing field of investigation. The mild, organocatalytic generation of elusive ortho‐quinodimethane intermediates (oQDMs), derived from suitable heteroaromatic carbonyl‐ or carbonyl‐like pronucleophiles has recently proved successful in the synthesis of such peculiar chiral architectures via stereoselective [4+2] cycloadditions. This review provides an overview of the most important advances attained in this field over the last decade.

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“…In 2019, again Albrecht and co-workers proposed a similar strategy as their previous work on enamine-mediated cycloaddition with coumarin-3-carboxylic acid 1 and 2-alkyl-3-furfural 84 to develop 3,4-dihydrocoumarin 85 (Scheme 20). [41] The present work is functioning on aminocatalytic, dearomatizative, decarboxylative cascade reactions. Initially, condensation of aldehyde and amino catalyst takes place, followed by dearomatization of furan ring, leading to generation of dienamine, which participates in (4 + 2) cycloaddition.…”

Section: C-3 Substituted Coumarin-3-carboxylic Acidmentioning

confidence: 99%

Recent Advances in the Decarboxylative Strategy of Coumarin‐3‐carboxylic Acid

Patel,

Chikhalia

2023

ChemistrySelect

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Coumarin is a highly proficient scaffold with great effectiveness which uplifts emerging chemists to create coumarin derivatives using cutting‐edge synthetic techniques. However, severe reaction conditions are required to develop substituted coumarin analogous. Notably, the carboxylic acid group in coumarin has emerged as a flexible functionality facilitating the construction of coumarin‐containing building blocks, emphasizing the decarboxylative strategy. Use of the decarboxylative technique has tremendously increased, due to its ability to increase the reactivity of the substrate. Moreover, it is the most extensively investigated synthetic strategy incorporating various functionalities in coumarin nuclei. This review discusses the decarboxylative strategies for creating C‐3 and C‐4 substituted coumarin derivatives. It emphasizes various interactions, including catalyst‐based, catalyst‐free, Michael addition, cyclo addition, three components, oxidative, and photocatalytic system involving the decarboxylation process.

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Dearomatizative and Decarboxylative Reaction Cascade in the Aminocatalytic Synthesis of 3,4‐Dihydrocoumarins

Cited by 16 publications

References 60 publications

The potential of Myosoton aquaticum extracts and compounds to control barnyardgrass (Echinochloa crus‐galli)

The potential of Myosoton aquaticum extracts and compounds to control barnyardgrass (Echinochloa crus‐galli)

Shaping Chirality via Stereoselective, Organocatalytic [4+2] Cycloadditions involving Heterocyclic ortho‐Quinodimethanes

Recent Advances in the Decarboxylative Strategy of Coumarin‐3‐carboxylic Acid

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