A Four‐Component Reaction for the Synthesis of Dioxadiazaborocines

Flagstad, Thomas; Petersen, Mette T.; Nielsen, Thomas E.

doi:10.1002/anie.201502989

Cited by 32 publications

(18 citation statements)

References 33 publications

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“…It is noteworthy that two boronic acids of similar electronic nature can be used for this four-component transformation, but this requires sequential additions. 128…”

Section: Four-component Petasis Reactionsmentioning

confidence: 99%

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

2019

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The Petasis boron–Mannich reaction, simply referred to as the Petasis reaction, is a powerful multicomponent coupling reaction of a boronic acid, an amine, and a carbonyl derivative. Highly functionalized amines with multiple stereogenic centers can be efficiently accessed via the Petasis reaction with high levels of both diastereoselectivity and enantioselectivity. By drawing attention to examples reported in the past 8 years, this Review demonstrates the breadth of the reactivity and synthetic applications of Petasis reactions in several frontiers: the expansion of the substrate scope in the classic three-component process; nonclassic Petasis reactions with additional components; Petasis-type reactions with noncanonical substrates, mechanism, and products; new asymmetric versions assisted by chiral catalysts; combinations with a secondary or tertiary transformation in a cascade- or sequence-specific manner to access structurally complex, natural-product-like heterocycles; and the synthesis of polyhydroxy alkaloids and biologically interesting molecules.

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“…It is noteworthy that two boronic acids of similar electronic nature can be used for this four-component transformation, but this requires sequential additions. 128…”

Section: Four-component Petasis Reactionsmentioning

confidence: 99%

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

2019

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“…BAs offer attractive opportunities for the discovery of fluorescent supramolecular architectures, since this function may be used to rigidify unreported structures of tridentate π‐conjugated ligands, which can be further tuned, depending on the BA structure. Bearing this in mind, we envisioned that Schiff‐base ligands could be used as a platform to build fluorescent boronates, since the modular structure of these ligands can be specifically engineered to accommodate BAs in form of a conformationally stable π‐conjugated complex (Scheme D) . The result of this design effort is a modular fluorophore platform based on boronic acid salicylidenehydrazone (BASHY) complexes.…”

Section: Introductionmentioning

confidence: 99%

A Three‐Component Assembly Promoted by Boronic Acids Delivers a Modular Fluorophore Platform (BASHY Dyes)

Santos

Rosa

Candeias

et al. 2015

Chemistry A European J

104

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The modular assembly of boronic acids with Schiff‐base ligands enabled the construction of innovative fluorescent dyes [boronic acid salicylidenehydrazone (BASHY)] with suitable structural and photophysical properties for live cell bioimaging applications. This reaction enabled the straightforward synthesis (yields up to 99 %) of structurally diverse and photostable dyes that exhibit a polarity‐sensitive green‐to‐yellow emission with high quantum yields of up to 0.6 in nonpolar environments. These dyes displayed a high brightness (up to 54 000 m −1 cm−1). The promising structural and fluorescence properties of BASHY dyes fostered the preparation of non‐cytotoxic, stable, and highly fluorescent poly(lactide‐co‐glycolide) nanoparticles that were effectively internalized by dendritic cells. The dyes were also shown to selectively stain lipid droplets in HeLa cells, without inducing any appreciable cytotoxicity or competing plasma membrane labeling; this confirmed their potential as fluorescent stains.

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“…The hydrazido alcohols S49-4 obtained using this protocol were subjected to a cyclization reaction in relation to the corresponding oxadiazolones and oxazolidinones, that is the target compounds of the work due to their possible antibacterial activity. Later on, the same authors [183] reported a four-component Petasis-type reaction that was used for the synthesis of dioxadiazaborocines.…”

Section: Chemical Transformations Of Indolylboronic Acid Derivativesmentioning

confidence: 99%

Indolylboronic Acids: Preparation and Applications

et al. 2019

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Indole derivatives are associated with a variety of both biological activities and applications in the field of material chemistry. A number of different strategies for synthesizing substituted indoles by means of the reactions of indolylboronic acids with electrophilic compounds are considered the methods of choice for modifying indoles because indolylboronic acids are easily available, stable, non-toxic and new reactions using indolylboronic acids have been described in the literature. Thus, the aim of this review is to summarize the methods available for the preparation of indolylboronic acids as well as their chemical transformations. The review covers the period 2010–2019.

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A Four‐Component Reaction for the Synthesis of Dioxadiazaborocines

Cited by 32 publications

References 33 publications

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

A Three‐Component Assembly Promoted by Boronic Acids Delivers a Modular Fluorophore Platform (BASHY Dyes)

Indolylboronic Acids: Preparation and Applications

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