Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel–Crafts Alkylation Strategy

Мамедов, В. А.; Mamedova, Vera L.; Kadyrova, Saniya F.; Galimullina, Venera R.; Хикматова, Гульназ З.; Korshin, Dmitry E.; Gubaidullin, А. Т.; Krivolapov, Dmitry B.; Ризванов, И. Х.; Bazanova, Olga B.; Sinyashin, Оleg G.; Latypov, Shamil K.

doi:10.1021/acs.joc.8b01871

Cited by 20 publications

(34 citation statements)

References 54 publications

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“…3,4‐Dimethoxycarbonyl‐2‐( p‐ methoxyphenyl)‐ N ‐( p‐ methylphenyl)‐1,2‐dihydroquinoline (4 e) . The Standard Procedure 1 was followed by use of 2‐silylphenyl triflate 1 a (55.1 mg, 0.184 mmol, 1.0 equiv), Schiff base 2 e [39] (45.7 mg, 0.203 mmol, 1.1 equiv), DMAD ( 3 a , 31.3 mg, 0.221 mmol, 1.2 equiv), and CsF (35.5 mg, 0.221 mmol, 1.2 equiv) in THF (2.0 mL). After the reaction mixture was stirred at 40 °C for 12 h, it was quenched and worked up.…”

Section: Methodsmentioning

confidence: 99%

“…The Standard Procedure 1 was followed by use of 2-silylphenyl triflate 1 a (55.1 mg, 0.184 mmol, 1.0 equiv), Schiff base 2 e [39] N-(p-Chlorophenyl)-3,4-dimethoxycarbonyl-2-phenyl-1,2-dihydroquinoline (4 f). The Standard Procedure 1 was followed by use of 2silylphenyl triflate 1 a (342 mg, 1.14 mmol, 1.0 equiv), Schiff base 2 g [40] (272 mg, 1.26 mmol, 1.1 equiv), DMAD (3 a, 195 mg, 1.37 mmol, 1.2 equiv), and CsF (208 mg, 1.37 mmol, 1.2 equiv) in THF (3.5 mL).…”

Section: 4-dimethoxycarbonyl-2-(p-methoxyphenyl)-n-(p-methylphenyl)mentioning

confidence: 99%

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Domino Processes of Arynes Reacting with Three Classes of Nucleophiles for Organic Syntheses

et al. 2021

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Synthetic application of arynes is broadened by their reactions with neutral N-, Sand nd O-containing nucleophiles to produce three types of compounds. Accordingly, 1,2-dihydroquinolines are synthesized from Schiff bases, alkynes, and arynes through a Diels-Alder reaction. Epoxides are prepared from thioethers and arynes along with aldehydes or ketones through a Johnson-Corey-Chaykovsky reaction. Phenolic ethers are produced from allyl ethers and arynes through a Claisen-type rearrangement. These target molecules, including natural products γ-asarone, asaricin, and a cholesteryl phenolic ether, are formed through reactions initiated by arynes. These new reactions share a prevailing feature of domino processes, which are carried out in a single flask and afford the desired products in good to high yields.

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Section: Methodsmentioning

confidence: 99%

Section: 4-dimethoxycarbonyl-2-(p-methoxyphenyl)-n-(p-methylphenyl)mentioning

confidence: 99%

Domino Processes of Arynes Reacting with Three Classes of Nucleophiles for Organic Syntheses

et al. 2021

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“…The synthesis of viridicatol also has recently been reported by other groups. As an example, Mamedov and coworkers developed a two-step process to 3-hydroxy-4-arylquinolin-2(1H)-ones starting with a Darzens condensation followed by an intramolecular Friedel-Crafts alkylation [18]. Dichloroacetanilide 7 reacts with 3-nitrobenzaldehyde in a Darzens condensation to produce epoxide 8, which in an intramolecular Friedel-Crafts alkylation with acetic acid and sulfuric acid produces quinolinone 9.…”

Section: Scheme 2 Kobayashi and Harayama's Synthesis Of Viridicatolmentioning

confidence: 99%

Marine Heterocyclic Compounds That Modulate Intracellular Calcium Signals: Chemistry and Synthesis Approaches

et al. 2021

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Intracellular Ca2+ plays a pivotal role in the control of a large series of cell functions in all types of cells, from neurotransmitter release and muscle contraction to gene expression, cell proliferation and cell death. Ca2+ is transported through specific channels and transporters in the plasma membrane and subcellular organelles such as the endoplasmic reticulum and mitochondria. Therefore, dysregulation of intracellular Ca2+ homeostasis may lead to cell dysfunction and disease. Accordingly, chemical compounds from natural origin and/or synthesis targeting directly or indirectly these channels and proteins may be of interest for the treatment of cell dysfunction and disease. In this review, we show an overview of a group of marine drugs that, from the structural point of view, contain one or various heterocyclic units in their core structure, and from the biological side, they have a direct influence on the transport of calcium in the cell. The marine compounds covered in this review are divided into three groups, which correspond with their direct biological activity, such as compounds with a direct influence in the calcium channel, compounds with a direct effect on the cytoskeleton and drugs with an effect on cancer cell proliferation. For each target, we describe its bioactive properties and synthetic approaches. The wide variety of chemical structures compiled in this review and their significant medical properties may attract the attention of many different researchers.

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“…Recently, this group synthesized 3‐hydroxy‐4‐arylquinolin‐2‐ones 172 through Darzens reaction between 2,2‐dichloro‐ N ‐methyl‐ N ‐phenylacetamide 173 and aromatic aldehydes under basic conditions (Scheme ) . The product distribution is highly dependent on the electronic nature of the substituent present in the aromatic ring.…”

Section: αα‐Dihaloketones As Building Blocks In Organic Synthesismentioning

confidence: 99%

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

Sadhukhan

Santhi

Baire

2020

Chemistry A European J

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The α,α‐dihalocarbonyl moiety is a bifunctional system with a gem‐dihalocarbon and a carbonyl carbon in 1,2‐fashion. This is one of the privileged scaffolds in medicinal chemistry due to its chemical and metabolic stability and lipophilicity. They have also been found in numerous structurally divergent natural products and most of their fabricated structures have already been in medicinal use. Apart from their important use in medicinal chemistry, the α,α‐dihalocarbonyl groups have been employed as key building blocks for the development of novel synthetic strategies and utilized as intermediates in total synthesis. In addition to the traditional transformations such as oxidations, reductions, and C−C bond formations, recently several new and non‐classical reactions have also been developed. This review provides short description of existing methods for their synthesis and detailed discussion on the efforts for the discovery and development of new reactions by employing α,α‐dihaloketones as synthetic building blocks. We have presented their use as key functional groups for the synthesis of polycyclic systems of medicinal and material importance and natural products.

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Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel–Crafts Alkylation Strategy

Cited by 20 publications

References 54 publications

Domino Processes of Arynes Reacting with Three Classes of Nucleophiles for Organic Syntheses

Domino Processes of Arynes Reacting with Three Classes of Nucleophiles for Organic Syntheses

Marine Heterocyclic Compounds That Modulate Intracellular Calcium Signals: Chemistry and Synthesis Approaches

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

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