Polycyclic heterocycles by condensation of 1,4-benzoquinone analogs and nucleophiles

Singh, R. P.; Prakash, Rashmi; Dehaen, Wim

doi:10.1016/bs.aihch.2021.01.002

Cited by 5 publications

(4 citation statements)

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“…The Nenitzescu reaction is the condensation of an enamine and a quinone and is a wellestablished synthetic pathway towards 5-hydroxyindole and benzofuran derivatives [1,2]. These classes of compounds exhibit promising activities for a variety of pharmaceutic applications, e.g., as antiviral agents [3][4][5][6][7][8][9][10], anti-inflammatory drugs [11][12][13][14], anticancer agents [15][16][17], and anti-arrhythmic agents [18].…”

Section: Introductionmentioning

confidence: 99%

“…The Nenitzescu reaction has been successfully carried out under various conditions, including the use of (Lewis) acids, in the absence of acid, with different solvents and at varying temperatures [1,2,[24][25][26]. The course of the reaction depends heavily on the reaction conditions and the structure of the starting materials [1,2,[24][25][26]. Moreover, 5-hydroxyindoles are generally formed in an oxidation-reduction pathway [27][28][29] (Scheme 1A).…”

Section: Introductionmentioning

confidence: 99%

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Exploration of the Divergent Outcomes for the Nenitzescu Reaction of Piperazinone Enaminoesters

et al. 2023

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The Nenitzescu reaction is a condensation reaction between an enamine and a quinone, which can give rise to a wide variety of reaction products depending on the nature of the starting material and the reaction conditions. The most commonly observed products are 5-hydroxyindoles and 5-hydroxybenzofurans. Both classes are of interest since they are known to possess a variety of promising bioactivities. Despite the high chemodivergency for this reaction, it remains an interesting synthetic strategy thanks to the mild reaction conditions, easily accessible starting materials and simple reaction procedures. For these reasons, our research group investigated the Nenitzescu reaction of piperazinone enaminoesters, resulting in the unexpected formation of rearranged 2-imidazolidinone benzofurans. In this work, we aimed to develop reaction conditions that favor the formation of 5-hydroxyindoles via an extensive, multivariate optimization study. This led to valuable insights into the parameters that influence regio- and chemoselectivity. Furthermore, two novel products were obtained, a pyrrolo[2,3-f]indole and a benzofuranone, both of which are rarely reported in the literature.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Exploration of the Divergent Outcomes for the Nenitzescu Reaction of Piperazinone Enaminoesters

et al. 2023

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“…One of the most prevalent and easily accessible building blocks for the synthesis of bicyclic and polyheterocyclic skeletons is 1,4-benzoquinones. 9 For instance, the formal [3 + 2] cycloaddition of alkenes with 1,4-benzoquinones promoted by acids offers a special way to construct benzofuran skeletons (Scheme 1a). 10 However, this strategy is inapplicable to the construction of oxaspiros due to the following factors: (1) steric bulk makes it difficult to build quaternary carbon and (2) the construction of benzofuran and simultaneous loading of another heterocycle at position 2 via a spiroannulation reaction remain challenging.…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis of spiro diheterocycles via multi-component dicyclization reaction

Wang

Zhao

et al. 2022

Org. Biomol. Chem.

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“…Ailanthoidol, a neolignan derivative, has been reported to have antiviral, antioxidant and antifungal activities [4]. Furthermore, most of compounds prepared from 2acetylbenzofurans have antimicrobial, antitumor, antiinflammatory, fungicidal, and weed-killing activities and may be used for treatment of cardiac arrhythmias [5][6][7][8][9][10][11][12]. It was observed from the literature that certain five membered heterocyclic compounds possess interesting biological activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Molecular Docking Studies of Novel 2-(5- Bromobenzofuran-2-Yl)-5-Substitutedphenyl-1,3,4-Oxadiazole Derivatives

Sanjeeva

Rao

Ramana

et al. 2021

JASR

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A series of 2-(5-bromobenzofuran-2-yl)-5-substitutedphenyl-1,3,4-oxadiazoles were synthesized in good yields using 5- bromobenzofuran-2-carbohydrazide and characterized by analytical and spectral data. Auto Dock 4.0/ADT program was used to investigate binding interaction of oxadiazole derivatives to Asp kinase. Asp kinase of Mycobacterium tuberculosis (MTB) is a type II topoisomerase and is a well-established and validated target for the development of novel therapeutics. The search was based on the Lamarckian genetic algorithm and the results were analyzed using binding energy. Analysis was based on lowest docked energy and inhibition constant values. Among the tested compounds, 3g, 3a, 3hand 3f derivatives of oxadiazole showed highest binding energy with the lowest inhibition constant. From the observed results it is concluded that 3g, 3a, 3h and 3f showed more affinity to Asp Kinase protein.

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Polycyclic heterocycles by condensation of 1,4-benzoquinone analogs and nucleophiles

Cited by 5 publications

References 489 publications

Exploration of the Divergent Outcomes for the Nenitzescu Reaction of Piperazinone Enaminoesters

Exploration of the Divergent Outcomes for the Nenitzescu Reaction of Piperazinone Enaminoesters

Efficient synthesis of spiro diheterocycles via multi-component dicyclization reaction

Synthesis, Characterization and Molecular Docking Studies of Novel 2-(5- Bromobenzofuran-2-Yl)-5-Substitutedphenyl-1,3,4-Oxadiazole Derivatives

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