The generation and chemistry of dianions derived from furancarboxylic acids

Knight, David W.; Nott, Andrew P.

doi:10.1039/p19810001125

Cited by 67 publications

(41 citation statements)

References 5 publications

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“…5-Methylfuran-2-carboxylic acid (14) [36] Upon cooling in an acetone/dry ice bath, a solution of 2-furancarboxylic acid (13, 2.24 g, 20 mmol, dried at 100°C) in 20 ml anhydrous THF was added dropwise to a mixture of 33 ml (60 mmol) 1.8 M lithium diisopropylamide in THF/hexane/ethylbenzole (Aldrich) and 80 ml of anhydrous THF. After 15 min at −70 to −60°C, a red-brown solution evolved, to which 2.5 ml (40 mmol) methyl iodide was added.…”

Section: Materials and Chemicalsmentioning

confidence: 99%

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Synthesis, characterization, and in vitro evaluation of the selective P2Y2 receptor antagonist AR-C118925

Rafehi

Burbiel

Attah

et al. 2016

Purinergic Signalling

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The G q protein-coupled, ATP-and UTP-activated P2Y 2 receptor is a potential drug target for a range of different disorders, including tumor metastasis, inflammation, atherosclerosis, kidney disorders, and osteoporosis, but pharmacological studies are impeded by the limited availability of suitable antagonists. One of the most potent and selective antagonists is the thiouracil derivative AR-C118925. However, this compound was until recently not commercially available and little is known about its properties. We therefore developed an improved procedure for the synthesis of AR-C118925 and two derivatives to allow up-scaling and assessed their potency in calcium mobilization assays on the human and rat P2Y 2 receptors recombinantly expressed in 1321N1 astrocytoma cells. The compound was further evaluated for inhibition of P2Y 2 receptor-induced β-arrestin translocation. AR-C118925 behaved as a competitive antagonist with pA 2 values of 37.2 nM (calcium assay) and 51.3 nM (β-arrestin assay). Selectivity was assessed vs. related receptors including P2X, P2Y, and adenosine receptor subtypes, as well as ectonucleotidases. AR-C118925 showed at least 50-fold selectivity against the other investigated targets, except for the P2X1 and P2X3 receptors which were blocked by AR-

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Section: Materials and Chemicalsmentioning

confidence: 99%

“…The first step, leading to 5-methylfuran-2-carboxylic acid (14), a selective lithiation/methylation procedure, was inspired by the work of Knight and Nott [36]. It proved to be crucial that a large volume of solvent was used, as otherwise salts precipitated and a mixture of products was formed.…”

Section: Synthesismentioning

confidence: 99%

Synthesis, characterization, and in vitro evaluation of the selective P2Y2 receptor antagonist AR-C118925

Rafehi

Burbiel

Attah

et al. 2016

Purinergic Signalling

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“…22,23 The first work concerning the generation of dianions directly from furan-2-carboxylic acid (2) was published by Knight and Nott. 24 The authors demonstrated the formation of dianion species by regioselective deprotonisation of acid 2 in the position H-5 with LDA and its reactivity with D 2 O and other more or less reactive electrophiles, except CO 2 . On the other hand, Carpenter and Chadwick investigated the course of lithiation of acid 2, using nbutyllithium and found that the regioselectivity is strongly dependent on the type of the lithium base.…”

Section: Resultsmentioning

confidence: 99%

“…Based on these facts, we decided to focus on a shorter and more effective synthesis of FDCA 1 in order to prepare and isolate it in pure form directly from furan-2-carboxylic acid (2) using carbon dioxide (Scheme 1). The whole practical process till addition of the electrophile was carried out according to literature using LDA 24 and n-butyllithium, 25 respectively. The usual treatment with saturated aqueous NH 4 Cl followed by extraction with ether allowed the solution of lithium furan-2,5-dicarboxylate which was subsequently acidified with 2N HCl at 0 °C.…”

Section: Resultsmentioning

confidence: 99%

One-step synthesis of furan-2,5-dicarboxylic acid from furan-2-carboxylic acid using carbon dioxide

Fischer¹,

Fišerová²

2013

Arkivoc

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A short and effective method for preparation and isolation of furan-2,5-dicarboxylic acid has been developed. Furan-2,5-dicarboxylic acid was prepared directly from furan-2-carboxylic acid in one step under strong basic conditions using carbon dioxide. This method allows to obtain the product with high added value, furan-2,5-dicarboxylic acid, from natural sources such as hemicelluloses containing pentoses.

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“…Although amide and oxazoline DMGs have found considerable application, the carboxylic acid DMG in furans and thiophenes and their benzo analogues are arguably the most useful for further manipulation (Scheme 11) [21]. An instructive illustration is the use of furan carboxylic acid 35 in the synthesis of sesquiterpenoid 37 via the diester 36, which is prepared by condensation of an anhydride with dianion of 35, the basic character of which appears to have minimal detrimental effects (Scheme 12) [22].…”

Section: Furans and Thiophenesmentioning

confidence: 99%

The Directed ortho Metalation Reaction – A Point of Departure for New Synthetic Aromatic Chemistry

Hartung

Snieckus

2002

Modern Arene Chemistry

159

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After a brief allusion to the current status of synthetic aromatic chemistry, a tour based on the Directed ortho Metalation (DoM) strategy is provided with selections from recent literature which highlight a) the use of DoM for the regiospecific preparation of polysubstituted aromatics and heteroaromatics; b) the valuable symbiosis of DoM with transition metal catalyzed AraAr cross-coupling protocols; c) the extension of DoM to the Directed remote Metalation (DreM) concept in biaryls, which provides methodologies for the construction of condensed aromatics (fluorenones, phenanthrols) and heterocyclics (thioxanthones, xanthones, acridones, dibenzphosphorinones, dibenzthiepinone dioxides, dibenzoxepinones, dibenzazepinones, dibenzphosphinones); and d) the evolving links of DoM to other modern methodologies with a note on the DoM-Grubbs ring-closing metathesis connection. The presentation is solely methodologically rather than total synthesis oriented; dependable directed metalation groups (DMGs ¼ CONR 2 , OCONR 2 , SONR 2 , NHBoc), new and renewed, are emphasized; p-excessive (furan, thiophene, indole) and p-deficient (pyridine) heterocycle HetDoM chemistry is delineated. While definitely not comprehensive, this account attempts to give a flavor of current anionic aromatic chemistry in synthesis. 10.1Scheme 1. Synthetic approaches to substituted aromatics. 10.2 The DoM Reaction as a Methodological Tool 331 Scheme 3. DoM chemistry generalizations. 10.2 The DoM Reaction as a Methodological Tool 333 Scheme 5. The N-cumyl sulfonamide DMG. Scheme 6. The N-cumyl carbamate DMG. 10.2 The DoM Reaction as a Methodological Tool 335 Scheme 9. The di-tert-butyl phosphine oxide DMG. 10.3 Heteroaromatic Directed ortho Metalation (HetDoM) in Methodological Practice 337

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The generation and chemistry of dianions derived from furancarboxylic acids

Cited by 67 publications

References 5 publications

Synthesis, characterization, and in vitro evaluation of the selective P2Y2 receptor antagonist AR-C118925

Synthesis, characterization, and in vitro evaluation of the selective P2Y2 receptor antagonist AR-C118925

One-step synthesis of furan-2,5-dicarboxylic acid from furan-2-carboxylic acid using carbon dioxide

The Directed ortho Metalation Reaction – A Point of Departure for New Synthetic Aromatic Chemistry

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