Potassium Phosphate‐Mediated Synthesis of C4‐Phosphorylated Quinolines via Cascade Cycloisomerization of Ynones DOI Open Access
Yi‐Feng Qiu,

Jin-Hao Li,

Qiang Wang

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 5, 2024

Abstract A cascade phosphorylation cycloisomerization of readily accessible ynones and diphenylphosphine oxides facilitated by potassium phosphate is described, allowing for the straightforward synthesis C4‐phosphorylated quinoline scaffolds. The formation a C−P bond C−N achieved in single procedure without need pre‐assembled cores prior to phosphorylation. This transformation operates requirement metals or oxidants exhibits excellent compatibility with various functional groups. Furthermore, antimicrobial activity evaluation demonstrated that synthesized derivatives exhibited potent inhibitory against Staphylococcus aureus.

Язык: Английский

Photocatalytic Umpolung Strategy for the Synthesis of α-Amino Phosphine Oxides and Deuterated Derivatives DOI
Chunhua Ma, Xiaofeng Li,

Xiya Chen

и другие.

Organic Letters, Год журнала: 2023, Номер 25(44), С. 8016 - 8021

Опубликована: Окт. 30, 2023

Direct, economical, and green synthesis of deuterated α-amino phosphine oxides remains an elusive challenge in synthetic chemistry. Herein, we report a visible-light-driven umpolung strategy for synthesizing from isocyanide using 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene as the photocatalyst D2O deuterium source. Moreover, streamlined sustainable methodology can be applied modification amino acids, natural products, drugs. The strong antiproliferative activity desired products indicates that method could provide novel privileged scaffold antitumor drug development.

Язык: Английский

Процитировано

29

Electrochemical radical annulation of 2-alkynyl biaryls with diselenides under catalyst- and chemical oxidant-free conditions DOI

Jun Jiang,

Keli Wang, Xiao Li

и другие.

Chinese Chemical Letters, Год журнала: 2023, Номер 34(12), С. 108699 - 108699

Опубликована: Июнь 17, 2023

Язык: Английский

Процитировано

27

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024 DOI
Martha C. Mayorquín‐Torres, Andreas Simoens, Eli Bonneure

и другие.

Chemical Reviews, Год журнала: 2024, Номер 124(12), С. 7907 - 7975

Опубликована: Май 29, 2024

The increasing importance of azaheterocyclic phosphonates in the agrochemical, synthetic, and medicinal field has provoked an intense search development synthetic routes for obtaining novel members this family compounds. This updated review covers methodologies established since 2004, focusing on synthesis phosphonates, which phosphonate moiety is directly substituted onto to structure. Emphasizing recent advances, classifies newly developed approaches according ring size providing information biological activities whenever available. Furthermore, summarizes various methods formation C–P bonds, examining sustainable such as Michaelis–Arbuzov reaction, Michaelis–Becker Pudovik Hirao coupling, Kabachnik–Fields reaction. After analyzing applications investigated years, a predominant focus evaluation these compounds anticancer agents evident. emerging underline versatility potential compounds, highlighting need continued research expand interesting family.

Язык: Английский

Процитировано

14

Photocatalytic Synthesis of Indanone, Pyrone, and Pyridinone Derivatives with Diazo Compounds as Radical Precursors DOI
Yang Xie,

Ye‐Peng Bao,

Xiao-Yan Zhuo

и другие.

Organic Letters, Год журнала: 2024, Номер 26(7), С. 1393 - 1398

Опубликована: Фев. 12, 2024

We disclose herein a photocatalytic radical cascade cyclization of diazoalkanes for the divergent synthesis important carbocycles and heterocycles. Under optimal reaction conditions, various indanone, pyrone, pyridinone derivatives can be obtained in moderate to good yields. Mechanistic experiments support formation carbon-centered radicals from through proton-coupled electron transfer process. Scale-up using continuous flow technology useful downstream application formed heterocycles further render strategy attractive valuable.

Язык: Английский

Процитировано

10

Visible-Light-Induced Acylative Pyridylation of Styrenes DOI
Zhiqin Zhang, Jianwei Wang,

Chenfeng Yu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(22), С. 4727 - 4732

Опубликована: Май 29, 2024

A visible-light-induced photocatalyst-free acylative pyridylation of styrenes with 4-acyl-1,4-dihydropyridines (DHPs) and 4-cyanopyridines has been described, featuring mild reaction conditions, a broad substrate scope, good functional group tolerance. The could also be performed under sunlight irradiation albeit slightly lower conversion. 4-Acyl-1,4-DHPs serve dual role, acting as both photoreductant to reduce the cyanopyridine its radical anion intermediate precursor produce acyl radical. mechanism was especially elucidated through Hammett analysis, quadratic linear regression analysis by using parameters, σmb σjj·. findings from further demonstrate that rate-limiting step process is single electron transfer between 4-acyl-1,4-DHPs 4-cyanopyridines.

Язык: Английский

Процитировано

8

Visible‐Light‐Driven Cyclizations DOI Creative Commons
Emilia Oueis, Mirella Elkadi, Ramón Rios

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(4), С. 635 - 697

Опубликована: Янв. 13, 2024

Abstract In recent years, the interest to develop cyclizations promoted by visible light has been gaining a lot of attention due its sustainability aspect. this review, we summarize most important advances in period describing methods used generate different ring sizes, while focusing on mechanistic details these reactions.

Язык: Английский

Процитировано

7

Visible-Light-Induced Highly Site-Selective Direct C–H Phosphorylation of Pyrrolo[2,3-d]pyrimidine Derivatives with H-Phosphine Oxides DOI
Zhuo Zhang, Mingrui Liu, Min Liu

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 2996 - 3009

Опубликована: Фев. 15, 2024

An efficient and highly regioselective C6-phosphorylation protocol for pyrrolo[2,3-d]pyrimidine (7-DAP) derivatives with various H-phosphine oxides induced by visible light at room temperature is described the first time. This has been successfully achieved combination of Na2-eosin Y as a photocatalyst LPO an oxidant under transition metal- additive-free conditions. The broad substrate scope, good functional group tolerance, excellent regioselectivity, air tolerant conditions make this process favorable modification scaffold enrich phosphorylated 7-DAP compounds further biological evaluation.

Язык: Английский

Процитировано

7

Expedient radical phosphonylations via ligand to metal charge transfer on bismuth DOI Creative Commons
Jatin Patra, Akshay M. Nair, Chandra M. R. Volla

и другие.

Chemical Science, Год журнала: 2024, Номер 15(19), С. 7136 - 7143

Опубликована: Янв. 1, 2024

Herein, we have developed efficient radical phosphonylations tailored upon visible-light mediated LMCT on bismuth. Phosphonylation of a broad range substrate classes was carried out under mild energy conditions using BiCl 3 as the catalyst.

Язык: Английский

Процитировано

7

3DPAFIPN as a halogenated dicyanobenzene-based photosensitizer catalyzed gram-scale photosynthesis of pyrano[2,3-d]pyrimidine scaffolds DOI Creative Commons
Farzaneh Mohamadpour

Scientific Reports, Год журнала: 2023, Номер 13(1)

Опубликована: Авг. 12, 2023

Abstract Utilizing the Knoevenagel–Michael tandem cyclocondensation reaction of barbituric acid/1,3-dimethylbarbituric acid, malononitrile, and aryl aldehydes, a sustainable methodology for photosynthesis pyrano[2,3- d ]pyrimidine scaffolds has been devised. The present study expounds on development green radical synthetic approach toward this class compounds. In study, novel halogenated dicyanobenzene-based photosensitizer was utilized in an aqueous solution, exposed to air at room temperature, activated by blue LED as renewable energy source purpose generating energy. primary aim endeavor is employ recently developed, easily obtainable, affordably priced cyanoarene-based donor–acceptor (D–A). 3DPAFIPN [2,4,6-tris(diphenylamino)-5-fluoroisophthalonitrile]} photocatalyst, thermally delayed fluorescence (TADF), capable inducing single electron transfer (SET) upon irradiation with visible light, thereby offering facile efficient high degree effectiveness, efficiency, eco-friendliness. aforementioned phenomenon facilitates exploration temporal changes that have occurred interactions between surroundings chemical constituents. aimed investigate turnover number (TON) frequency (TOF) scaffolds. Additionally, it demonstrated gram-scale cyclization viable method utilization industrial applications.

Язык: Английский

Процитировано

14

Photocatalytic Bicyclization of Indole-Tethered 1,6-Enynes for Diastereoselective Synthesis of Pyrrolo[3,2,1-jk]carbazoles DOI
Hang‐Dong Zuo, Xi Chen,

Ya‐Yu Yuan

и другие.

Organic Letters, Год журнала: 2024, Номер 26(18), С. 3810 - 3815

Опубликована: Апрель 28, 2024

A visible-light-driven photocatalytic protocol is established for the diastereoselective synthesis of pyrrolo[3,2,1-jk]carbazoles via a radical-triggered multicomponent bicyclization reaction starting from readily available indole-tethered 1,6-enynes and α-benzyl-α-bromomalonates under mild conditions. This approach exhibits wide substrate compatibility excellent tolerability toward various functional groups boasts benefit efficient ring formation chemical bond creation.

Язык: Английский

Процитировано

6