Design and Synthesis of Rigid‐Featured Tertiary Amine‐Derived C₂‐Symmetric Chiral Furan‐N,N′‐dioxide Ligands

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(42)

Опубликована: Авг. 19, 2023

Abstract To expand the chemical space of chiral N ‐oxides and furan‐containing ligands, herein we designed synthesized a new class rigid‐featured tertiary amine‐derived C 2 ‐symmetric furan‐ , N′ ‐dioxide (Fu‐2NO) ligands from optically pure l ‐prolinamides/hydroxylprolinamides in operationally simple two steps up to 57 % overall yield. The newly developed Fu‐2NO possesses pyrroloimidazolone‐based as non‐flat walls, afforded opportunity for fine‐tuning ligand electronic conformational properties by judicious choice substituent nonligating nitrogen atom. More importantly, can tolerate air moisture such that no special handling is needed their storage, be applied Ni(II)‐catalyzed asymmetric Friedel‐Crafts alkylation reaction indole.

Язык: Английский

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Construction of bridged cyclic N,O-ketal spirooxindoles through a Michael addition/N,O-ketalization sequence

Organic & Biomolecular Chemistry, Год журнала: 2018, Номер 16(10), С. 1751 - 1759

Опубликована: Янв. 1, 2018

The first highly diastereoselective TfOH-catalyzed Michael addition/N,O-ketalization sequence of 3-aminooxindoles and ortho-hydroxychalcones was achieved, delivering a wide range bridged cyclic N,O-ketal spirooxindoles with complex strained structures in 41-97% yields. Moreover, gram-scale experiment some chemical conversions were conducted to further demonstrate the synthetic value.

Язык: Английский

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Synthesis and Applications of 9H‐Pyrrolo[1,2‐a]indole and 9H‐Pyrrolo[1,2‐a]indol‐9‐one Derivatives

European Journal of Organic Chemistry, Год журнала: 2019, Номер 2019(31-32), С. 5133 - 5150

Опубликована: Авг. 7, 2019

This review covers the strategies for synthesis of 9 H ‐pyrrolo[1,2‐ a ]indole and ]indol‐9‐one derivatives. Both metal‐promoted or non‐metal catalyzed transformations will be developed, including some relevant applications.

Язык: Английский

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Diastereoselective construction of 4-indole substituted chromans bearing a ketal motif through a three-component Friedel–Crafts alkylation/ketalization sequence

RSC Advances, Год журнала: 2018, Номер 8(28), С. 15641 - 15651

Опубликована: Янв. 1, 2018

The first TfOH-catalyzed three-component Friedel-Crafts alkylation/ketalization sequence of indoles, alcohols and ortho-hydroxychalcones was developed to afford a wide range 4-indole substituted chromans bearing ketal motif in 77-99% yields. Notably, only simple filtration needed purify them. By altering methanol CHCl3, 2,4-bisindole chroman with the same indole substituent at C2 C4 positions afforded. Moreover, different substituents could be obtained by treatment monosubstituted another molecule.

Язык: Английский

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

Molecules, Год журнала: 2024, Номер 29(12), С. 2748 - 2748

Опубликована: Июнь 9, 2024

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

Язык: Английский

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Copper-Catalyzed Synthesis of Coumarins. A Mini-Review

Catalysts, Год журнала: 2021, Номер 11(11), С. 1382 - 1382

Опубликована: Ноя. 16, 2021

Coumarin (2H-chromen-2-one) derivatives have important uses in medicinal and synthetic chemistry, for example, as fluorescent probes. These properties prompted chemists to develop efficient methods synthesize the coumarin core and/or functionalize it. In this context, many metal-catalyzed syntheses of coumarins been introduced; among them, copper-catalyzed reactions appear be very promising owing non-toxicity cheapness copper complexes. mini-review, results field are summarized. We hope stimulate other applications these complexes preparation derivatives.

Язык: Английский

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A Ru(ii)-catalyzed C–H activation and annulation cascade for the construction of highly coumarin-fused benzo[a]quinolizin-4-ones and pyridin-2-ones

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(11), С. 2680 - 2687

Опубликована: Янв. 1, 2023

A reaction involving a Ru( ii )-catalyzed C–H activation and annulation cascade was successfully established for constructing coumarin-fused benzo[ ]quinolizin-4-ones pyridin-2-ones.

Язык: Английский

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Synthesis of Structurally Diversified Benzo[c]chromene Derivatives under (An)aerobic Conditions Catalyzed by CuI

Journal of Heterocyclic Chemistry, Год журнала: 2019, Номер 56(10), С. 2822 - 2830

Опубликована: Сен. 2, 2019

2‐Bromobenzoic acids underwent an α ‐arylation with cyclohexane‐1,3‐diones to give 1 H ‐benzo[ c ]chromene‐1,6(2 )‐diones under Ar atmosphere catalyzed by CuI/ l ‐proline in the presence of Cs 2 CO 3 . The subsequent regioselective oxidation took place O balloon automatically based on substituents for construction structurally diversified benzo[ ]coumarin derivatives.

Язык: Английский

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Synthesis of tris(indolyl)methanes by using dimethyl carbonate as a single carbon source via C-H functionalization approach

Chemical Papers, Год журнала: 2023, Номер 78(2), С. 1117 - 1124

Опубликована: Ноя. 3, 2023

Язык: Английский

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A general and convenient method for the synthesis of 2,4-dinitrobenzyl ketones. Almost unlimited access to 2-substituted 6-nitroindoles from 2,4-dinitrotoluene and aldehydes

New Journal of Chemistry, Год журнала: 2018, Номер 42(5), С. 3260 - 3269

Опубликована: Янв. 1, 2018

Starting from 2,4-dinitrotoluene and aldehydes, 2-substituted 6-nitroindoles with alkyl, cycloalkyl, aryl heteroaryl (thienyl, furyl, pyridyl) substituents in the 2-position of indole ring were synthesized. This methodology can be used for synthesis indoles non-racemic substituents.

Язык: Английский

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