Synthesis and enantiomeric recognition studies of optically active 5,5-dioxophenothiazine bis(urea) and bis(thiourea) derivatives

Pál, Dávid; Móczár, Ildikó; Kormos, Attila; Baranyai, Péter; Huszthy, Péter

doi:10.1016/j.tetasy.2016.08.002

Cited by 6 publications

(2 citation statements)

References 49 publications

(23 reference statements)

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“…Receptor 58 showed the best chiral recognition for amino acids protected with Boc and Piv; for amino acids protected with a formyl group, the effect on enantioselectivity was negligible. The same phenothiazine derivative was then used to obtain a series of ligands 59-62 (Figure 19) and to investigate their stereo-differentiating properties [50]. The effects of the acidity of the hydrogen bond donors and the size of the aromatic substituent linked to the thio(urea) function via a methine bridge were examined.…”

Section: Urea and Thiourea Receptorsmentioning

confidence: 99%

Recognition of Chiral Carboxylates by Synthetic Receptors

Niedbała¹,

Dąbrowa²,

Wasiłek³

et al. 2021

Molecules

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Recognition of anionic species plays a fundamental role in many essential chemical, biological, and environmental processes. Numerous monographs and review papers on molecular recognition of anions by synthetic receptors reflect the continuing and growing interest in this area of supramolecular chemistry. However, despite the enormous progress made over the last 20 years in the design of these molecules, the design of receptors for chiral anions is much less developed. Chiral recognition is one of the most subtle types of selectivity, and it requires very precise spatial organization of the receptor framework. At the same time, this phenomenon commonly occurs in many processes present in nature, often being their fundamental step. For these reasons, research directed toward understanding the chiral anion recognition phenomenon may lead to the identification of structural patterns that enable increasingly efficient receptor design. In this review, we present the recent progress made in the area of synthetic receptors for biologically relevant chiral carboxylates.

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Section: Urea and Thiourea Receptorsmentioning

confidence: 99%

Recognition of Chiral Carboxylates by Synthetic Receptors

Niedbała¹,

Dąbrowa²,

Wasiłek³

et al. 2021

Molecules

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“…The optically active 5,5‐dioxophenothiazine‐bis‐thiourea derivative 64 was prepared in moderate yields from the phenothiazine‐1,9‐diamine 63 and the appropriate ( S )‐1‐arylethyl isothiocyanate 15 in pyridine under argon at room temperature for 2 days (Scheme ) .…”

Section: Synthetic Routes To Bis‐thioureasmentioning

confidence: 99%

Bis‐thiourea Derivatives and Their Utility in Synthesis of Mono‐heterocyclic, Bis‐heterocyclic, and Fused Heterocyclic Systems

Dawood

2019

Journal of Heterocyclic Chem

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Bis‐thiourea derivatives have distinguished synthetic potentialities. They are interesting substrates for construction of various classes of heterocycles, such as thiazoles, thiadiazoles, imidazoles, bis‐thiazoles, bis‐thiadiazoles, and fused heterocyclic systems. The current review is concerned on disclosing the synthetic and research applications of bis‐thioureas that were reported in the literature during the last decade.

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Enantioselective recognition of carboxylic acids by novel fluorescent triazine‐based thiazoles

Halay

Bozkurt

2017

Chirality

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Hydrogen bonding and π-π interactions take special part in the enantioselectivity task. In this regard, because of having both hydrogen acceptor and hydrogen donor groups, melamine derivatives become more of an issue for enantioselectivity. In the light of such information, triazine-based chiral, fluorescence active novel thiazole derivatives L1 and L2 were designed and synthesized from (S)-(-)-2-amino-1-butanol and (1S,2R)-(+)-2-amino-1,2-diphenylethanol. The structural establishment of these compounds was made by spectroscopic methods such as FTIR, H, and C NMR. While the solution of these compounds in DMSO did not show any fluorescence emission, it was observed that the emission increased 44-fold for L1 and 55-fold for L2 in 95% water, similar to the aggregation-induced emission (AIE) characterized compounds. In this regard, enantioselective capabilities of these compounds against carboxylic acids were tested, and in experiments carried out at a ratio of 40/60 DMSO/H O, it was determined that R-2ClMA increased the fluorescence emission of L1 chiral receptor by 2.59 times compared to S-isomer.

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Synthesis and enantiomeric recognition studies of optically active 5,5-dioxophenothiazine bis(urea) and bis(thiourea) derivatives

Cited by 6 publications

References 49 publications

Recognition of Chiral Carboxylates by Synthetic Receptors

Recognition of Chiral Carboxylates by Synthetic Receptors

Bis‐thiourea Derivatives and Their Utility in Synthesis of Mono‐heterocyclic, Bis‐heterocyclic, and Fused Heterocyclic Systems

Enantioselective recognition of carboxylic acids by novel fluorescent triazine‐based thiazoles

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