Recent Advances of Three‐component Reactions of Simple Indoles DOI
Zhan‐Yong Wang,

Zhantong Liu,

Aili Sun

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 11(8)

Опубликована: Июнь 16, 2022

Abstract Indoles are extremely important and versatile building blocks in the field of chemistry. This review highlights advance made three‐component reactions indoles between 2011–2021. The reaction types classified into three categories based on trigger mechanisms. Reactions with alkenes, alkynes, aldehydes, imines, ketones, S, Se, etc discussed. In order to highlight mechanisms involved, this has provided specific analysis inside a gray box each scheme. We hope these studies will promote future research indole area.

Язык: Английский

Photoredox Radical Cascade Cyclization of 2‐Alkynylarylnitriles in Visible Light: Direct Access to 3‐Amino‐1‐indenones DOI

Shruti Rajput,

Dikshita Garg,

Nidhi Jain

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(9), С. 2072 - 2078

Опубликована: Март 1, 2024

Abstract A photoinduced direct synthesis of 3‐amino‐1‐indenones via radical cascade cyclization strategy is demonstrated. The methodology involves a domino reaction between 2‐alkynylarylnitrile and N ‐aminopyridinium salt captures the reactivity in‐situ generated nitrogen‐centered (NCR) in visible light. Multiple bond‐forming events including C−N, C−C, C−O take place sequentially on enabling construction 3‐amino‐1‐indenone core at room temperature 35–76% yield. preliminary biological screening synthesized compounds indicative their potent anti‐cancer property.

Язык: Английский

Процитировано

3

Conjugated 1,8 and 1,6 Addition of Bis-Trimethylsilylketene Acetal to Activated p-Quinone Methides via Trifluoromethanesulfonic Anhydride DOI Creative Commons
Luis J. Benítez‐Puebla, Ricardo Ballinas-Indilí, Marcos Flores-Álamo

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 31, 2025

In this work, we studied the conjugated additions of bis-trimethylsilylacetalketene acetals (bis-TMSKA) to para-quinone methides (p-QMs), which are one most explored molecules for study and gained significant attention in organic chemistry due their versatile reactivity, particularly Michael addition reactions. study, trifluoromethanesulfonic anhydride (Tf2O) was used as an activating agent p-QMs, aiming achieve 1,6-Michael products least reported 1,8-Michael with pyridine substituents. The reactivity p-QMs derived from demonstrated distinct reaction pathways, leading formation δ γ lactones. investigation also involved synthesizing a 1-indanone carboxylic acids obtained 1,6-addition.

Язык: Английский

Процитировано

0

Visible Light-Promoted Three-Component Reaction for the Synthesis of Pyrrolopyrazoles DOI

Han‐Peng Pan,

Shao‐Shuai Chen,

Han Yang

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 15, 2025

A visible light-enabled three-component cascade assembles pyrrolopyrazoles from arylalkynes, benzoquinones, and 5-aminopyrazole through a mechanistically validated carbonyl-alkyne metathesis/(3 + 2)-cycloaddition/1,2-aryl migration sequence. This protocol delivers pyrrolopyrazole heterocycles in up to 96% yield with excellent functional group tolerance. Preliminary biological screening identified promising antitumor activity selected products, highlighting the potential value of this method. The proposed reaction mechanism is supported by control experiments.

Язык: Английский

Процитировано

0

Pd and photoredox dual catalysis assisted decarboxylative ortho-benzoylation of N-phenyl-7-azaindoles DOI

Shruti Rajput,

Ramandeep Kaur, Nidhi Jain

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(7), С. 1453 - 1461

Опубликована: Янв. 1, 2022

The directing group assisted decarboxylative ortho-benzoylation of N-aryl-7-azaindoles with α-keto acids has been achieved by synergistic visible light promoted photoredox and palladium catalysis. approach tenders rapid entry to aryl ketone architectures from simple acid precursors via the in situ generation a benzoyl radical intermediate. transformation provides range ortho-benzoylated N-aryl-7-azaindoles, excellent site-selectivity good functional compatibility under mild reaction conditions. Biological target predictions indicate that these molecules may serve as potential anti-cancer anti-viral agents.

Язык: Английский

Процитировано

13

Visible light-mediated synthesis of α-alkoxy/hydroxy diarylacetaldehydes from terminal alkynes DOI
Jaswant Kumar,

Ajaz Ahmed,

Sourav Kumar

и другие.

New Journal of Chemistry, Год журнала: 2022, Номер 46(22), С. 10967 - 10973

Опубликована: Янв. 1, 2022

A visible light-mediated approach enabling the use of alcohols as nucleophiles in a one-step synthesis α-alkoxy/hydroxy diarylacetaldehydes is reported.

Язык: Английский

Процитировано

13

Visible‐Light‐Mediated [2+2] Photocycloadditions of Alkynes DOI
Qing‐Bao Zhang,

Feng Li,

Bin Pan

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер 30(43)

Опубликована: Май 29, 2024

Visible-light-mediated [2+2] photocycloaddition reaction can be considered an ideal solution due to its green and sustainable properties, is one of the most efficient methods synthesize four-membered ring motifs. Although research on alkynes challenging because diminished reactivity alkynes, more significant strain products, remarkable achievements have been made in this field. In article, we highlight recent advances visible-light-mediated reactions with focus mechanism late-stage synthetic applications. Advances obtaining cyclobutenes, azetines, oxetene active intermediates continue breakthroughs fascinating field research.

Язык: Английский

Процитировано

3

Visible‐Light‐Induced Paternò‐Büchi Reaction of Anthraquinones for the Synthesis of Spirocyclic Oxetanes DOI

Xiangwen Xu,

Fanyuanhang Yang,

Xiaofeng Zhang

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(5)

Опубликована: Март 30, 2023

Abstract Reported here is a general visible‐light‐induced Paternò‐Büchi reaction between anthraquinones and olefins lead to the formation of diverse anthraquinone‐based spirocyclic oxetanes which served as an important scaffold in natural drugs products. This approach negates need for UV light, thus overcome synthetic limitations traditional reaction. Therefore, method reported characterized by high regioselectivity, simple operations, mild conditions broad scope.

Язык: Английский

Процитировано

7

Enantioselective synthesis of α,α-diarylketones by sequential visible light photoactivation and phosphoric acid catalysis DOI Creative Commons
Hong‐Fu Liu, Long Liang, Zhiqiang Zhu

и другие.

Science Advances, Год журнала: 2023, Номер 9(24)

Опубликована: Июнь 16, 2023

Chiral ketones and their derivatives are useful synthetic intermediates for the synthesis of biologically active natural products medicinally relevant molecules. Nevertheless, general broadly applicable methods enantioenriched acyclic α,α-disubstituted ketones, especially α,α-diarylketones, remain largely underdeveloped, owing to easy racemization. Here, we report a visible light photoactivation phosphoric acid–catalyzed alkyne-carbonyl metathesis/transfer hydrogenation one-pot reaction using arylalkyne, benzoquinone, Hantzsch ester expeditious α,α-diarylketones with excellent yields enantioselectivities. In reaction, three chemical bonds, including C═O, C─C, C─H, formed, providing de novo chiral α,α-diarylketones. Moreover, this protocol provides convenient practical method synthesize or modify complex bioactive molecules, efficient routes florylpicoxamid BRL-15572 analogs. Computational mechanistic studies revealed that C-H/π interactions, π-π interaction, substituents all play crucial roles in stereocontrol reaction.

Язык: Английский

Процитировано

7

Visible light induced reactions of quinones DOI

Jeffrey Jang,

G.‐H. LEE,

Eun Jin Cho

и другие.

Bulletin of the Korean Chemical Society, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 17, 2024

Abstract This review covers the visible light induced reactions of quinones such as benzoquinone, naphthoquinone, and anthraquinone. These are distinguished by their fully conjugated structures, which feature minimal energy gaps, nonbonding electron pairs on oxygen atoms. Such structural attributes facilitate n p → π* transition, allowing for easy access to excited states rendering highly reactive under visible‐light irradiation. We describe three primary types facilitated these electronic characteristics: Paternò–Büchi (PB) reactions, entail [2 + 2] photocycloaddition between carbonyl groups alkenes or alkynes; CH activation processes, showcase quinones' versatility in functionalizing hydrocarbons; formation donor–acceptor complexes, demonstrating capability engage charge transfer interactions. Through this review, we highlight critical role play photochemistry, unique properties, broad applicability synthetic organic chemistry.

Язык: Английский

Процитировано

2

Photoredox Hydroxy-arylation of the Terminal Double Bond of N-Substituted 3-Methyleneisoindolin-1-ones in Visible Light DOI
Rohit Kumar, V.K. Jain, Nidhi Jain

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(18), С. 11939 - 11946

Опубликована: Авг. 30, 2022

Mild and efficient ruthenium-catalyzed hydroxy-arylation of the terminal double bond N-substituted 3-methyleneisoindolin-1-ones is described. The reaction takes place with aryl diazonium salt as arylating reagent water hydroxyl source in visible light at ambient temperature. strategy entails vicinal difunctionalization alkene enables construction 3-benzyl-3-hydroxyisoindolin-1-one heterocyclic scaffolds moderate to good yields. C-C C-O bonds are formed one pot without any external additive oxidant through an situ generation a carbocation intermediate green light.

Язык: Английский

Процитировано

9