A Three‐Component Synthesis of 3‐Functionally Substituted 5,6‐Dihydropyrrolo[2,1‐<i>a</i>]isoquinolines

Miftyakhova, Almira R.; Борисова, Т. Н.; Титов, А. А.; Sidakov, Matvey B.; Новиков, Роман А.; Efimov, Ilya; Варламов, А. В.; Voskressensky, Leonid G.

doi:10.1002/cbdv.202100584

Cited by 8 publications

(2 citation statements)

References 34 publications

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“…The latest publications of our group have focused on the development and optimization of three-component syntheses of 5,6-dihydropyrrolo[2,1- a ]isoquinolines based on transformations of 1-aroyl-3,4-dihydroisoquinolines in the presence of electron-deficient alkynes (methylpropiolate and acetylacetylene) and CH or NH acids . The described domino reactions make it possible to obtain highly functionalized pyrrolo[2,1- a ]isoquinolines having pharmacophoric groups at position 3 (Scheme a).…”

Section: Resultsmentioning

confidence: 99%

Pseudo Four-Component Synthesis of 5,6-Dihydroindolo[2,1-a]isoquinolines

Miftyakhova,

Borisova,

Fakhrutdinov

et al. 2024

J. Org. Chem.

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An easy synthesis of novel highly functionalized 5,6-dihydroindolo[2,1-a]isoquinolines was developed via a pseudo four-component domino reaction of 1-aroyl-3,4-dihydroisoquinolines, terminal α,β-ynones, and malononitrile. The selective formation of this biologically relevant heterocyclic core was achieved using a one-pot approach under microwave irradiation. The formation of the same skeleton through the reaction of 5,6-dihydropyrrolo[2,1-a]isoquinolines with malonic acid dinitrile supports the proposed mechanism, involving the intermediate product of the three-component reaction. Furthermore, the disproval of an alternative reaction pathway, which involved the dimerization of malononitrile followed by three-component transformation, was demonstrated. Introducing the malononitrile dimer as a CH acid resulted in the formation of a different pyrido[3′,4′:4,5]pyrrolo[2,1-a]isoquinoline core. Additionally, the synthesized 5,6-dihydroindolo[2,1-a]isoquinolines were examined for their photophysical properties, revealing their attractive luminescent characteristics.

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Section: Resultsmentioning

confidence: 99%

Pseudo Four-Component Synthesis of 5,6-Dihydroindolo[2,1-a]isoquinolines

Miftyakhova,

Borisova,

Fakhrutdinov

et al. 2024

J. Org. Chem.

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“…The possibility of performing biological assays, as well as for the detailed study of their chemical behavior, is caused by their synthetic availability. Among the existing strategies for the synthesis of pyrrolo[1,2- a ]quinolines and pyrrolo[2,1- a ]isoquinolines, the most powerful and versatile is the formal [3 + 2]-cycloaddition reaction between quinolinium or isoquinolinium ylides and various dipolarophiles.…”

Section: Introductionmentioning

confidence: 99%

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

Osipov,

Demidov,

Artemenko

et al. 2024

J. Org. Chem.

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Various substituted pyrrolo[1,2-a]quinolines and pyrrolo[2,1-a]isoquinolines were synthesized in good to high yields by the Et3N-mediated reaction of push–pull 3-nitrobenzofurans or 1-Ts-/1-Ms-3-nitroindoles and precursors of carbonyl-stabilized quinolinium and isoquinolinium ylides as 1,3-dipole equivalents. These transformations proceed in a one-pot manner starting with the formal [3 + 2]-cycloaddition stage, which is accompanied by double dearomatization of both quinoline/isoquinoline and benzofuran/indole moieties, followed by ring-opening of cyclic intermediate formed and nitrous acid elimination sequence. [3 + 2]-Cycloadducts were isolated as the final products in cases of impossibility or difficulty of their enolization. The present protocol was successfully extended to 3-nitro-4H-chromene derivatives as push–pull dipolarophile component. Finally, using the method of competing reactions, the reactivity of the starting compounds was compared with each other.

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Six-membered ring systems: pyridines and benzo derivatives

Badenock

2023

Progress in Heterocyclic Chemistry

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A Three‐Component Synthesis of 3‐Functionally Substituted 5,6‐Dihydropyrrolo[2,1‐a]isoquinolines

Cited by 8 publications

References 34 publications

Pseudo Four-Component Synthesis of 5,6-Dihydroindolo[2,1-a]isoquinolines

Pseudo Four-Component Synthesis of 5,6-Dihydroindolo[2,1-a]isoquinolines

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

Six-membered ring systems: pyridines and benzo derivatives

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