Dihydronaphthofurans: synthetic strategies and applications

Olyaei, Abolfazl; Sadeghpour, Mahdieh

doi:10.1039/c9ra09987e

Cited by 12 publications

(9 citation statements)

References 96 publications

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“…(1.36 g, 68%) of 5aa from a single experiment. The AQ directing group was then easily removed by treatment with HCl (6 M) upon heating (41), providing two distinct free carboxylic acid products, each of which possess a privileged core structure found in biologically active small molecules (42)(43)(44).…”

Section: Scope Of Bis-nucleophilesmentioning

confidence: 99%

Redox-Paired Alkene Difunctionalization Enables Skeletally Divergent Synthesis

Karunananda

Zeng

et al. 2022

Preprint

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Multi-step organic synthesis enables conversion of simple chemical feedstocks into a more structurally complex product that serves a particular function. The target compound is forged over several steps, with concomitant generation of byproducts in each step to account for underlying mechanistic features of the reactions (e.g., redox processes). To map structure–function relationships, libraries of molecules are often needed, and these are typically prepared by iterating an established multi-step synthetic sequence. An underdeveloped approach is designing organic reactions that generate multiple valuable products with different carbogenic skeletons in a single synthetic operation. Taking inspiration from paired electrosynthesis processes that are widely used in commodity chemical production (e.g., conversion glucose to sorbitol and gluconic acid), we report a palladium-catalyzed reaction that converts a single alkene starting material into two skeletally distinct products in a single operation through a series of carbon–carbon and carbon–heteroatom bond forming events enabled by mutual oxidation and reduction, a process that we term redox-paired alkene difunctionalization. We demonstrate the scope of the method in enabling simultaneous access to reductively 1,2-diarylated and oxidatively [3+2]-annulated products, and we explore the mechanistic details of this unique catalytic system using a combination of experimental techniques and density functional theory (DFT). The results described herein establish a distinct approach to small-molecule library synthesis that can increase the rate of compound production. Furthermore, these findings demonstrate how a single transition metal catalyst can mediate a sophisticated redox-paired process through multiple pathway-selective events along the catalytic cycle.

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Section: Scope Of Bis-nucleophilesmentioning

confidence: 99%

Redox-Paired Alkene Difunctionalization Enables Skeletally Divergent Synthesis

Karunananda

Zeng

et al. 2022

Preprint

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“…These observations prompted us to undertake the investigation of naphthofuran with oxadiazole and indole as second heterocyclic components. Some of the derivatives of naphthofurans which show biological and pharmacological activities are given below the biologic properties of a new oral antifertility agent, 2-phenyl-3-p-(β-pyrrolidinoethoxy)-phenyl [2,1-b]naphthofuran (146) (Figure 7) [79] have been investigated in detail on rodent species and rhesus monkeys the rhesus macaque (Macaca mulatta) is native throughout Asia and is considered to have the largest native range of any non-human primate by Kamboj et al [80].…”

Section: Biologically Active Naphthofuransmentioning

confidence: 99%

Synthesis, reactions and applications of naphthofurans: A review

Abdelwahab

Fekry

2021

Eur J Chem

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Considering the highly important biological and medicinal properties of naphthofurans, the synthesis of these heterocycles has attracted the interest of medicinal and organic chemists. This review aims to describe the different strategies developed so far for the synthesis of naphthofurans and their applications and the literature reports for the period of 2000 to early 2020. After a brief introduction of the types of naphthofurans and their biological activities, the different synthetic approaches such as chemical and photochemical, methods are described and organized on the basis of the catalysts and the other reagents employed in the syntheses. Some of the reactions have been applied successfully to the synthesis of biologically important compounds.

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“…However, since most of the protocols reported in the literature [ 29 , 30 ] suffer from some limitations, such as, for instance, the substrate scope and the possibility to obtain differently functionalized products, the development of more versatile methods is still a topic of interest. In this context, nitrostyrenes have been considered as useful annulation reagents in the reaction with naphthols, because of their ability to react as double electrophiles with the bidentate naphthol enolate, generated in situ under basic conditions.…”

Section: Introductionmentioning

confidence: 99%

An Easy Access to Furan-Fused Polyheterocyclic Systems

et al. 2022

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Nitrostilbenes characterized by two different or differently substituted aryl moieties can be obtained from the initial ring-opening of 3-nitrobenzo[b]thiophene with amines. Such versatile building blocks couple the well-recognized double electrophilic reactivity of the nitrovinyl moiety (addition to the double bond, followed by, e.g., intramolecular replacement of the nitro group) with the possibility to exploit a conjugated system of double bonds within an electrocyclization process. Herein, nitrostilbenes are reacted with different aromatic enols provided by a double (carbon and oxygen) nucleophilicity, leading to novel, interesting naphthodihydrofurans. From these, as a viable application, aromatization and electrocyclization lead in turn to valuable polycondensed, fully aromatic O-heterocycles.

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Dihydronaphthofurans: synthetic strategies and applications

Abstract: Dihydronaphthofurans (DHNs) are an important class of arene ring-fused furans which are widely found in many natural and non-natural products and drug candidates with relevant biological and pharmacological activities.

Cited by 12 publications

References 96 publications

Redox-Paired Alkene Difunctionalization Enables Skeletally Divergent Synthesis

Redox-Paired Alkene Difunctionalization Enables Skeletally Divergent Synthesis

Synthesis, reactions and applications of naphthofurans: A review

An Easy Access to Furan-Fused Polyheterocyclic Systems

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