Recent advances in the synthesis of organoselenium heterocycle conjugates

Tetrahedron, Год журнала: 2024, Номер 157, С. 133957 - 133957

Опубликована: Март 23, 2024

Язык: Английский

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A critical review on the sustainable synthesis of pyrimidine-based heterocycles and their biological activities

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134626 - 134626

Опубликована: Март 1, 2025

Язык: Английский

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Visible‐Light‐Induced Domino Cyclization to Access Pyrido[2,3‐d]pyrimidine‐2,4‐diones via a Radical‐Polar Crossover Reaction

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(19), С. 2346 - 2350

Опубликована: Май 27, 2024

Comprehensive Summary Catalytic and green strategies for the synthesis of privileged scaffolds are synthetically appealing. We now report a radical‐polar crossover (RPC)‐enabled three‐component cyclization bromodifluoroalkyls with enaminones 6‐aminouraciles via visible‐light‐induced domino cyclization. The reaction exhibited broad substrate scope (> 40 examples) including complex molecules, which highlighted utility this strategy construction library bioactive analogs.

Язык: Английский

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CH‐Functionalization of Heterocycles with the Formation of C−O, C−N, C−S/Se, and C−P Bonds by Intermolecular Addition of Heteroatom‐Centered Radicals

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(11), С. 1714 - 1755

Опубликована: Апрель 12, 2023

Abstract In the last decade, free radicals have found a wide application in functionalization of unsaturated compounds, such as alkenes, alkynes, and arenes, via free‐radical addition to carbon‐carbon π‐bonds. these processes, intermolecular attack on aromatic substrates represents challenge due relatively high resistance π‐system reactions comparison alkene C=C bonds. The heterocycles is especially interesting diversity their structures chemical properties well importance for medicinal chemistry, agrochemistry, materials science. Addition C‐centered widely known Minisci‐type well‐reviewed. this paper, we summarized main achievements less explored group processes: by heteroatom‐centered (O‐, N‐, S‐/Se‐, P‐radicals) with emphasis papers published after 2010. Literature analysis revealed strong trend towards usage electrochemistry photoredox‐catalysis generation recent years. remaining fundamental problem field lack experimental support proposed mechanisms frequent existence several plausible reaction pathways. progress mechanistic studies can significantly improve prediction optimal conditions depending structure.

Язык: Английский

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Multicomponent Synthesis of Fluorescent Thiazole–Indole Hybrids and Thiazole-Based Novel Polymers

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(17), С. 11399 - 11413

Опубликована: Авг. 23, 2022

Herein, we report an efficient multicomponent reaction for the synthesis of trisubstituted thiazoles involving a one-pot C–C, C–N, and C–S bond-forming process from readily available starting materials. The arylglyoxal, indole, aryl thioamides in acetic acid medium under sealed heating conditions provided 3-(2,4-diarylthiazol-5-yl)-1H-indoles (4) good to excellent yields. Using similar strategy, thioamide, 2,5-dihydroxy-1,4-benzoquinone structurally interesting bis-thiazoles having dihydroxy-1,4-benzoquinone linker (9). All products were fully characterized by spectroscopic techniques. We also recorded single-crystal X-ray diffraction (XRD) compounds 4b 9a unambiguous structure determination. Indole-linked exhibit prominent fluorescence properties. relative quantum yields all thiazole-linked indoles measured dimethyl sulfoxide (DMSO) with respect quinine sulfate 0.1 M H2SO4 as reference. scope this was further explored preparing novel polymers 11a 11b using naphthalene/benzene-1,4-bis(carbothioamide) polymerization.

Язык: Английский

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HFIP-mediated multicomponent reactions for the synthesis of fluorescent quinoline-fused pyrroles

Tetrahedron, Год журнала: 2023, Номер 132, С. 133250 - 133250

Опубликована: Янв. 6, 2023

Язык: Английский

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Copper-Mediated C4-Benzylations of 5-Aminopyrazoles with 3-Indoleacetic Acids

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(11), С. 6623 - 6632

Опубликована: Май 11, 2023

Herein, we present a copper-mediated C4-benzylation of 5-aminopyrazoles with 3-indoleacetic acids. Various benzylated are prepared in good-to-excellent yields under basic and ligand-free conditions the presence copper acetate. Moreover, this benzylation method is applicable to other substrates, including naphthylamine, 2-aminochromen-4-one, enamines. Some products exhibit antiproliferative activities against cancer cell lines. In addition, C4-benzylated cyclized into 1H-pyrazolo[4',3':6,7]azepino[3,4-b]indoles aldehydes via one-pot two-step processes; notably, fluorescence emissions large Stokes shifts.

Язык: Английский

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Domino Reaction for the Synthesis of Pyrazole/Isoxazole Fused Naphthyridine Derivatives Involving Indole Ring Opening and Double Ring Formation

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(11), С. 6847 - 6856

Опубликована: Май 9, 2023

Herein, a hitherto unreported approach for the synthesis of pyrazole/isoxazole-fused naphthyridine derivatives by three-component domino reaction arylglyoxal monohydrate, 5-amino pyrazole/isoxazole, and indoles in acetic acid medium has been reported. In this method, four bonds (2 C-C 2 C-N) form one-pot with concomitant formation two new pyridine rings via indole ring opening double cyclization reactions. This methodology is also applicable gram-scale synthesis. The mechanism was studied isolating characterizing intermediates. Along complete characterization all products, structure product 4o unambiguously confirmed single crystal X-ray diffraction.

Язык: Английский

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Transition-Metal-Free Dehydrogenation of Benzyl Alcohol for C–C and C–N Bond Formation for the Synthesis of Pyrazolo[3,4-b]pyridine and Pyrazoline Derivatives

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 6039 - 6057

Опубликована: Апрель 26, 2023

A series of cascade reactions that produce a range functionalized aromatic heterocyclic compounds with pyrazole/pyrazoline cores have been developed. The method relies on metal-free dehydrogenative process to in-situ benzaldehydes. produced benzaldehyde was then allowed react some other substances, including acetophenone, pyrazole amine, and phenylhydrazine. intermediate from these substrates underwent several chemical processes, electrocyclization, the aza-Diels-Alder reaction, formation intramolecular C-N bonds. These positive outcomes would open up possibility producing biologically active pyrazolo[3,4-b]pyridine pyrazoline derivatives through variety possible reactions.

Язык: Английский

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Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

The Chemical Record, Год журнала: 2023, Номер 24(2)

Опубликована: Сен. 5, 2023

Dihydroazolopyrimidines are an important class of heterocycles that isosteric to natural purines and therefore great interest primarily as drug-like molecules. In contrast the heteroaromatic analogs, synthetic approaches these compounds were developed much later, their chemical properties biological activity have not been studied in detail until recently. review, different ways build dihydroazolopyrimidine systems from building blocks described - via initial formation a partially hydrogenated pyrimidine ring or azole ring, well one-pot assembly azine fragments. Special attention is given modern approaches: multicomponent reactions, green chemistry, use non-classical activation methods. Information on dihydroazolopyrimidines prospects for design drugs various profiles also summarized this review.

Язык: Английский

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