A regioselective synthesis of pentacyclic compounds containing coumarin, pyrrole, indene without catalysts under microwave irradiation

Chen, Zhiwei; Hou, Junbo; Dai, Zhaoran; Yang, Xiaofeng

doi:10.1016/j.cclet.2016.04.009

Cited by 13 publications

(1 citation statement)

References 26 publications

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“…Chen et al presented a regioselective synthesis of dihydrochromenoindeno[1,2- b ]pyrroles 20 , 21a – q in 70–92% yield via the reaction of N-substituted 4-aminocoumarin derivatives 5 , 18a – q with ninhydrin ( 19 ) under microwave irradiation without the presence of a catalyst [ 74 ]. Nucleophilic addition of 4-aminocoumarin ( 5 ) to the more electrophilic middle carbonyl of indanetrione, which is in equilibrium with ninhydrin, gave the intermediate A .…”

Section: Synthetic Strategies For the Preparation Of [34]-fused Pyrro...mentioning

confidence: 99%

An Overview of the Synthesis of 3,4-Fused Pyrrolocoumarins of Biological Interest

Kapidou,

Litinas

2024

Molecules

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3,4-Fused pyrrolocoumarins, synthetically prepared or naturally occurring, possess interesting biological properties. In this review, the synthetic strategies for the synthesis of the title compounds are presented along with their biological activities. Two routes are followed for that synthesis. In one, the pyrrole ring is formed from coumarin derivatives, such as aminocoumarins or other coumarins. In the other approach, the pyranone moiety is built from an existing pyrrole derivative or through the simultaneous formation of coumarin and pyrrole frameworks. The above syntheses are achieved via 1,3-dipolar cycloaddition reactions, Michael reaction, aza-Claisen rearrangement reactions, multi-component reactions (MCR), as well as metal-catalyzed reactions. Pyrrolocoumarins present cytotoxic, antifungal, antibacterial, α-glucosidase inhibition, antioxidant, lipoxygenase (LOX) inhibition, and fluorescent activities, as well as benzodiazepine receptor ability.

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Section: Synthetic Strategies For the Preparation Of [34]-fused Pyrro...mentioning

confidence: 99%

An Overview of the Synthesis of 3,4-Fused Pyrrolocoumarins of Biological Interest

Kapidou,

Litinas

2024

Molecules

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Ultrasound promoted three‐component synthesis of dihydroindeno[1,2‐b]pyrrole derivatives

Nasuhipur

Ghasemi

Shahrisa

et al. 2022

Journal of Heterocyclic Chem

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In this work, a one-pot three-component reaction of ninhydrin, primary amines, and 1,3-dicarbonyl compounds was investigated under various conditions to synthesis of diverse derivatives of dihydroindeno[1,2-b]pyrroles. Catalyst-free conditions in EtOH under ultrasound irradiation (45% of amplitude) were selected as a novel and efficient method for synthesis of these fused structures. The reactivity of different primary amines was then investigated for steric and electronic effects. Two examples of difunctional structures were also synthesized by using of 1,4-diaminobenzene under optimum conditions with high yields. The structure of all products was characterized by spectroscopic methods and elemental analysis.

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Synthesis and Antifungal Activity of 4‐ and 6‐(1H‐Pyrrol‐1‐yl) Coumarins, and their Thiocyanato Derivatives

et al. 2019

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Facile and efficient syntheses of 4‐(1H‐pyrrol‐1‐yl)‐coumarins and 6‐(1H‐pyrrol‐1‐yl)‐coumarins from the corresponding aminocoumarins are reported. The transformations were optimized and their corresponding scope and limitations were assessed. Selected (1H‐pyrrol‐1‐yl)‐coumarins were further subjected to a mild thiocyanation, undergoing selective functionalization on the pyrrole nucleus. A set of 10 differently substituted compounds was submitted to activity testing against various fungal strains. It was found that the introduction of a SCN moiety increased the antifungal activity, turning some compounds into fungicidal agents, to the point that one of the thiocyanato derivatives displayed an antifungal profile comparable to those of fluconazole and nystatin.

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A regioselective synthesis of pentacyclic compounds containing coumarin, pyrrole, indene without catalysts under microwave irradiation

Cited by 13 publications

References 26 publications

An Overview of the Synthesis of 3,4-Fused Pyrrolocoumarins of Biological Interest

An Overview of the Synthesis of 3,4-Fused Pyrrolocoumarins of Biological Interest

Ultrasound promoted three‐component synthesis of dihydroindeno[1,2‐b]pyrrole derivatives

Synthesis and Antifungal Activity of 4‐ and 6‐(1H‐Pyrrol‐1‐yl) Coumarins, and their Thiocyanato Derivatives

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