Efficient Post-Macrocyclization Functionalizations of Oxacalix[2]arene[2]pyrimidines

Rossom, Wim Van; Maes, Wouter; Kishore, Lingam; Ovaere, Margriet; Meervelt, Luc Van; Dehaen, Wim

doi:10.1021/ol702864y

Cited by 79 publications

(25 citation statements)

References 42 publications

(21 reference statements)

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“…Though cyclopyridines are obvious candidate hosts for cations, the methylene‐bridged cyclopyridine, calix[4]pyridine, does not appear to bind cations 59, 60. In the past decade, hetero‐bridged calixarenes61–64 such as thiacalixarene,65, 66 NH(NMe)‐bridged calixarene,67–76 and oxacalixarene77–88 attracted significant interest as potential cation binders without further functionalization. Although the recognition of cations clearly requires an appropriate conformation of the calixarene, the structural and conformational relationship of the parent and heteroatom‐bridged calix[4]arenes is unclear.…”

Section: Introductionmentioning

confidence: 99%

Semifield testing of a bioremediation tool for atrazine‐contaminated soils: Evaluating the efficacy on soil and aquatic compartments

Chelinho

Moreira‐Santos

Silva

et al. 2012

Enviro Toxic and Chemistry

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The present study evaluated the bioremediation efficacy of a cleanup tool for atrazine-contaminated soils (Pseudomonas sp. ADP plus citrate [P. ADP + CIT]) at a semifield scale, combining chemical and ecotoxicological information. Three experiments representing worst-case scenarios of atrazine contamination for soil, surface water (due to runoff), and groundwater (due to leaching) were performed in laboratory simulators (100 × 40 × 20 cm). For each experiment, three treatments were set up: bioremediated, nonbioremediated, and a control. In the first, the soil was sprayed with 10 times the recommended dose (RD) for corn of Atrazerba and with P. ADP + CIT at day 0 and a similar amount of P. ADP at day 2. The nonbioremediated treatment consisted of soil spraying with 10 times the RD of Atrazerba (day 0). After 7 d of treatment, samples of soil (and eluates), runoff, and leachate were collected for ecotoxicological tests with plants (Avena sativa and Brassica napus) and microalgae (Pseudokirchneriella subcapitata) species. In the nonbioremediated soils, atrazine was very toxic to both plants, with more pronounced effects on plant growth than on seed emergence. The bioremediation tool annulled atrazine toxicity to A. sativa (86 and 100% efficacy, respectively, for seed emergence and plant growth). For B. napus, results point to incomplete bioremediation. For the microalgae, eluate and runoff samples from the nonbioremediated soils were extremely toxic; a slight toxicity was registered for leachates. After only 7 d, the ecotoxicological risk for the aquatic compartments seemed to be diminished with the application of P. ADP + CIT. In aqueous samples obtained from the bioremediated soils, the microalgal growth was similar to the control for runoff samples and slightly lower than control (by 11%) for eluates.

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Section: Introductionmentioning

confidence: 99%

Semifield testing of a bioremediation tool for atrazine‐contaminated soils: Evaluating the efficacy on soil and aquatic compartments

Chelinho

Moreira‐Santos

Silva

et al. 2012

Enviro Toxic and Chemistry

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“…Ebenso beschrieben Dehaen et al. die Synthese verschiedenartig funktionalisierter Oxacalix[2]aren[2]pyrimidine 20 aus dem Bis(methylthio)‐substituierten Oxacalix[4]aren 19 (Schema ) 42. Durch Liebeskind‐Srogl‐Reaktionen wurden verschiedene Arylgruppen an die Pyrimidinringe gekuppelt (68–78 % Ausbeute).…”

Section: Anwendung In Der Organischen Syntheseunclassified

“…Durch Liebeskind‐Srogl‐Reaktionen wurden verschiedene Arylgruppen an die Pyrimidinringe gekuppelt (68–78 % Ausbeute). Die einstufige Arylierung nach der Makrocyclisierung war effizienter als der Aufbau des Makrocyclus aus den entsprechenden arylsubstituierten Dihalogenpyrimidin‐Komponenten 42…”

Section: Anwendung In Der Organischen Syntheseunclassified

Die C‐C‐Kreuzkupplung nach Liebeskind und Srogl

Prokopcová

Kappe

2009

Angewandte Chemie

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Über Schwefel zum Erfolg: Die Kreuzkupplung von organischen Schwefelverbindungen mit Boronsäuren unter neutralen Bedingungen in Gegenwart eines Palladium(0)‐Katalysators und einer stöchiometrischen Menge eines Kupfer(I)‐Cofaktors hat sich als wertvolle C‐C‐Verknüpfungsmethode etabliert (siehe Schema). Diese basenfreie Kupplung verläuft nach einem beispiellosen Mechanismus und hat deutliche Vorteile, wenn andere Pd0‐katalysierte Verfahren versagen. Um die Fülle an bereits bekannten hoch selektiven und zuverlässigen Methoden zur C‐C‐Bindungsknüpfung zu ergänzen, besteht ein wachsendes Interesse an der Entwicklung neuer Verfahren mit einer veränderten oder orthogonalen Reaktivität. Liebeskind und Srogl beschrieben 2000 eine übergangsmetallkatalysierte Kreuzkupplung von Thioestern mit Boronsäuren zur Synthese von Ketonen unter neutralen Bedingungen. Diese desulfurierende Kreuzkupplung verläuft unter Palladium(0)‐Katalyse mit stöchiometrischem Kupfer(I)‐Zusatz, folgt einem beispiellosen Mechanismus und ist auf eine Reihe von Organoschwefelderivaten und nucleophilen Organometallreagentien anwendbar. Hier betrachten wir neuere Anwendungen dieser faszinierenden Reaktion in der organischen Synthese. Besondere Berücksichtigung finden Fälle, bei denen herkömmliche Methoden der C‐C‐Bindungsbildung versagt haben.

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“…It is now well established that the presence of heteroaromatic moieties such as triazine, pyrimidine, and pyridine impart special properties to the macrocycles by virtue of which they can interact with the anions through anion-π interactions [34,35], and with metal cations through coordination [1,8,[36][37][38] in addition to providing hydrogen bond driven self-assemblies [39][40][41][42][43][44]. Therefore, we thought it worthwhile to incorporate such important heteroaromatic moieties in nucleophilic and electrophilic fragments needed for the construction of such macrocycles.…”

Section: Introductionmentioning

confidence: 99%

Suzuki-Miyaura Cross-Coupling Reaction of Dichloro-Heteroaromatics: Synthesis of Functionalized Dinucleophilic Fragments

Naseer

Abbas

Hameed

et al. 2014

J. Chil. Chem. Soc.

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The Suzuki-Miyaura cross-coupling reaction has successfully been applied for the synthesis of 4,4'-[6-(diethylamino)-1,3,5-triazine-2,4-diyl]diphenol (4a), 4,4'-(pyrimidine-4,6-diyl)diphenol (4b), 4,4'-(pyridine-2,6-diyl)diphenol (4c). The reaction of 4,6-dichloro-N,N-diethyl-1,3,5-triazin-2-amine (1a), 4,6-dichloropyrimidine (1b) and 2,6-dichloropyridine (1c) with p-methoxyphenylboronic acid (2) in the presence of palladium catalyst followed by demethylation reaction furnished the desired products in good to excellent yields. To test the reactivity of these nucleophiles, the compound 4a was further reacted with cyanuric chloride to get trimeric fragment (5a). All the compounds were characterized by their physical, spectral ( 1 H and 13 C NMR and Mass) and microanalytical data. These dinucleophilic fragments (4a-4c) having triazine, pyrimidine and pyridine rings, respectively, are excellent future candidates for the construction of large functional hetero-atom bridged macrocycles for diverse applications in host-guest chemistry, supramolecular catalysis, self-assembly and other related fields of supramolecular chemistry in addition to their potential in medicinal chemistry.

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Efficient Post-Macrocyclization Functionalizations of Oxacalix[2]arene[2]pyrimidines

Cited by 79 publications

References 42 publications

Semifield testing of a bioremediation tool for atrazine‐contaminated soils: Evaluating the efficacy on soil and aquatic compartments

Semifield testing of a bioremediation tool for atrazine‐contaminated soils: Evaluating the efficacy on soil and aquatic compartments

Die C‐C‐Kreuzkupplung nach Liebeskind und Srogl

Suzuki-Miyaura Cross-Coupling Reaction of Dichloro-Heteroaromatics: Synthesis of Functionalized Dinucleophilic Fragments

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