Base-Mediated Cascade Lactonization/1,3-Dipolar Cycloaddition Pathway for the One-Pot Assembly of Coumarin-Functionalized Pyrrolo[2,1-a]isoquinolines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8420 - 8434

Published: June 5, 2024

An elegant and highly concise strategy for the construction of coumarin-functionalized pyrrolo[2,1-a]isoquinolines from available propargylamines isoquinolinium N-ylides has been disclosed. In this reaction, acted as a C2 synthon to form coumarin ring well 1,3-dipole construct pyrrole in single pot. This cascade process involves 1,4-conjugate addition/lactonization/1,3-dipolar cycloaddition four chemical bonds (one C–O bond three C–C bonds) two new heterocyclic skeletons. Additionally, most these compounds showed good fluorescence properties exhibited high molar extinction coefficient large Stokes shifts.

Language: Английский

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Recent Advances in Biologically Active Coumarins from Marine Sources: Synthesis and Evaluation

Marine Drugs, Journal Year: 2022, Volume and Issue: 21(1), P. 37 - 37

Published: Dec. 31, 2022

Coumarin and its derivatives have significantly attracted the attention of medicinal chemists chemical biologists due to their huge range biological, in particular, pharmacological properties. Interesting families coumarins been found from marine sources, which has accelerated drug discovery process by inspiring innovation or even identification analogues with remarkable biological The purpose this review is showcase most interesting marine-derived a chemistry point view, as well novel useful synthetic routes described date achieve these structures. references that compose overview were collected PubMed, Mendeley SciFinder.

Language: Английский

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Progress on synthesis and structure-activity relationships of lamellarins over the past decade

European Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 269, P. 116294 - 116294

Published: March 6, 2024

Language: Английский

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An Overview on the Synthesis of Lamellarins and Related Compounds with Biological Interest

Molecules, Journal Year: 2024, Volume and Issue: 29(17), P. 4032 - 4032

Published: Aug. 26, 2024

Lamellarins are natural products with a [3,4]-fused pyrrolocoumarin skeleton possessing interesting biological properties. More than 70 members have been isolated from diverse marine organisms, such as sponges, ascidians, mollusks, and tunicates. There is continuous interest in the synthesis of these compounds. In this review, synthetic strategies for title compounds presented along their Three routes followed lamellarins. Initially, pyrrole derivatives starting or intermediate compounds, then they fused to isoquinoline coumarin moiety. Second, compound an indole last route, coumarins which moiety scaffold. The isolamellarins, azacoumestans, isoazacoumestans, analogues also described. above achieved via metal-catalyzed cross-coupling, [3 + 2] cycloaddition, substitution, lactonization reactions. exhibit cytotoxic, multidrug resistance (MDR), topoisomerase I-targeted antitumor, anti-HIV, antiproliferative, anti-neurodegenerative disease, anti-inflammatory activities.

Language: Английский

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Cascade Synthesis of Pyrrolo[1,2-a]quinolines and Pyrrolo[2,1-a]isoquinolines via Formal [3 + 2]-Cycloaddition of Push–Pull Nitro Heterocycles with Carbonyl-Stabilized Quinolinium/Isoquinolinium Ylides

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 9816 - 9829

Published: June 25, 2024

Various substituted pyrrolo[1,2-

Language: Английский

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Synthesis of 3,4-diarylisoxazoline <em>N</em>-oxides from nitrostilbenes and nitroacetates

Mendeleev Communications, Journal Year: 2025, Volume and Issue: 35(1), P. 22 - 23

Published: Jan. 1, 2025

Language: Английский

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Diaryl α-nitrostilbenes as nitro-substituted analogues of combretastatins: synthesis and biological evaluation in the sea urchin embryo model

Mendeleev Communications, Journal Year: 2025, Volume and Issue: 35(3), P. 274 - 277

Published: Jan. 1, 2025

Language: Английский

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(+)-Salsolidine in Synthesis of 5,6-Dihydropyrrolo[2,1-a]Isoquinolines

Chemistry of Natural Compounds, Journal Year: 2025, Volume and Issue: unknown

Published: May 17, 2025

Language: Английский

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Recent advances in the synthesis of chromenone fused pyrrolo[2,1-a]isoquinoline derivatives

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(48), P. 22246 - 22268

Published: Jan. 1, 2023

This review, from 2016 to 2022, summarizes advances in the synthesis of 2- and 4-chromenones fused five-membered ring pyrrolo[2,1- a ]isoquinolines diverse orientations highlighting modes construction by classical transition metal-catalyzed methods.

Language: Английский

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Visible‐Light‐Catalyzed Formal [3+2] Annulation‐Aromatization of Amidines with Isoquinolinium N‐Ylides: Access to Imidazo[2,1‐a]isoquinolines

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(21), P. 3629 - 3636

Published: Sept. 21, 2023

Abstract A visible‐light‐catalyzed formal [3+2] annulation‐aromatization reaction for the synthesis of various substituted imidazo[2,1‐ a ]isoquinolines from amidines with stabilized isoquinolinium N ‐ylides in presence bases is developed. The procedure reported here involves direct C−H activation and formation C−C/C−N bonds one‐pot. mechanism probed by radical‐trapping experiment, fluorescence quenching, light on/off experiments. late‐stage modification experiments provide potential applications field organic medicinal chemistry chemists.

Language: Английский

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