Une nouvelle voie d'accès aux benzofurannes

Hercouet, A.; Corre, M. Le

doi:10.1016/s0040-4039(01)86285-7

Cited by 64 publications

(35 citation statements)

References 2 publications

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“…Benzofuran derivatives 1 – 10 were synthesized according to the protocol outlined in Scheme . The key step for the formation of the benzofuran moiety was achieved by an intramolecular Wittig reaction between ortho ‐hydroxybenzyltriphosphonium salts IIa – IIg and the appropriate benzoyl chlorides 39. The desired Wittig reagent was readily prepared from the conveniently substituted ortho ‐hydroxybenzyl alcohol Ia – Ig and PPh 3 ⋅HBr 40–43.…”

Section: Resultsmentioning

confidence: 99%

Zinc Porphyrins with a Pyridine‐Ring‐Anchoring Group for Dye‐Sensitized Solar Cells

et al. 2013

Chemistry An Asian Journal

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Anchoring groups are extremely important in controlling the performance of dye-sensitized solar cells (DSCs). The design and characterization of sensitizers with new anchoring groups, in particular non-carboxylic acid groups, has become a recent focus of DSC research. Herein, new donor-π-acceptor zinc-porphyrin dyes with a pyridine ring as an anchoring group have been designed and synthesized for applications in DSCs. Photophysical and electrochemical investigations demonstrated that the pyridine ring worked effectively as an anchoring group for the porphyrin sensitizers. DSCs that were based on these new porphyrins showed an overall power-conversion efficiency of about 4.0 % under full sunlight (AM 1.5G, 100 mW cm(-2)).

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Section: Resultsmentioning

confidence: 99%

Zinc Porphyrins with a Pyridine‐Ring‐Anchoring Group for Dye‐Sensitized Solar Cells

et al. 2013

Chemistry An Asian Journal

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“…The key step for the formation of the benzofuran moiety was achieved by an intramolecular Wittig reaction between ortho-hydroxybenzyltriphosphonium salt and the appropriate benzoylchloride. 15 The desired Wittig reagent IIa-b was readily prepared from the conveniently substituted orthohydroxybenzyl alcohol Ia-b and PPh 3 ·HBr. …”

Section: Resultsmentioning

confidence: 99%

Synthesis of Nitro-Substituted 2-Phenylbenzofurans Derivatives as Potential Human Monoamine Oxidase Inhibitors<strong> </strong>

Delogu

2017

Proceedings of the 21st International Electronic Conference on Synthetic Organic Chemistry

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Abstract:Benzofuran (oxygen heterocycle) is a common moiety found in many biologically active natural and therapeutic products, and thus represents a very important pharmacophore. It is present in many medicinally important compounds that show biological activity, including anticancer and antiviral properties. Some benzofuran derivatives are also known as 5-lipoxygenase inhibitors, antagonists of the angiotensin II receptor, blood coagulation factor Xa inhibitors, ligands of adenosine A1 receptor and more recently as MAO inhibitors. In general, benzofurans described as MAO inhibitors have a higher selectivity to the MAO-B isoform. In our efforts to contribute to the development of novel compounds that may be useful in the treatment of neurodegenerative disorders such as PD or AD, we are focusing on 2-phenylbenzofuran derivatives. 2-Phenylbenzofurans have been selected by analogy to 3-phenylcoumarins previously described by us as potent and selective MAO-B inhibitors, and preserving the core of trans-stilbene in their structure. Based on these previous experimental results, and with the aim of finding novel and more selective MAO-B inhibitors, in the present work we continue our studies, describing the synthesis of a new series of nitro-substituted 2-phenylbenzofurans derivatives in order to compare experimental results. Keywords: Wittig reaction, 2-phenylbenzofuran, Monoamino oxidase (MAO)Introduction:

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“…The synthesis of the right-hand fragment 42 (Scheme 10) started from known iodide 43 [20] which was converted into carboxylic acid 45 by Myers alkylation of pseudoephedrine propionamide 44 [21] and subsequent amide hydrolysis. Esterification of 45 through the phenolic OH of the Wittig salt 46 and subsequent intramolecular Wittig reaction [22] of 47 delivered benzofuran 48, which was then converted into alkyl iodide 42 in two steps. The construction of the tetrahydropyran domain (Scheme 11) started with a Corey-Fuchs chain elongation of known aldehyde 49 [23] into alkynal 50.…”

Section: The First Total Synthesis By the Lee Group (2004)mentioning

confidence: 99%

In Pursuit of a Competitive Target: Total Synthesis of the Antibiotic Kendomycin

2010

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Kendomycin is a novel polyketide having a unique quinone methide ansa structure and an impressive biological profile. Herein we provide a chronological overview of the synthetic work towards the title compound. Thus far, over a period of about eight years, eight groups worldwide have published on their synthetic efforts resulting in five total syntheses, one formal synthesis, and a number of fragment syntheses. Most approaches roughly mimic the biogenetic pathway, starting with an aromatic polyphenol subunit to which a polyketide chain is attached. Subsequent key steps include macrocyclization and the formation of the densely substituted tetrahydropyran ring, and then a late-stage oxidation and lactol formation.

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Une nouvelle voie d'accès aux benzofurannes

Cited by 64 publications

References 2 publications

Zinc Porphyrins with a Pyridine‐Ring‐Anchoring Group for Dye‐Sensitized Solar Cells

Zinc Porphyrins with a Pyridine‐Ring‐Anchoring Group for Dye‐Sensitized Solar Cells

Synthesis of Nitro-Substituted 2-Phenylbenzofurans Derivatives as Potential Human Monoamine Oxidase Inhibitors<strong> </strong>

In Pursuit of a Competitive Target: Total Synthesis of the Antibiotic Kendomycin

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