Molecular-Oxygen-Mediated Multicomponent Oxidative Cyclization: Synthesis of Tertiary-Alcohol-Unit-Bearing N-Heterocycles via Transforming C–H to C–OH Bonds DOI

Xiaoshuang Guo,

Maozhong Miao, Peng Zhao

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 26, 2024

We developed a molecular-oxygen-mediated multicomponent oxidative cyclization strategy to synthesize N-heterocycles containing tertiary alcohol units via the formation of key C–OH bonds and quaternary carbon centers. This formal [3 + 2 1] annulation offers green sustainable alternative for de novo bond formation, using O2 as both oxidant oxygen source under metal- catalyst-free conditions. Notably, continuous [1,5]-hydrogen transfer together with excess alcohols promotes C–OH-bearing products. Additionally, generation centers inhibits conversion C═O bonds, thus stabilizing desired

Язык: Английский

Synthesis of functionalized quinolines from the cascade reactions of N-aryl amidines with two CF3-ynones via C–H/N–H/C–N/C–C bond cleavage DOI
Hao Li,

Shengnan Yan,

Yuanshuang Xu

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(7), С. 1917 - 1923

Опубликована: Янв. 1, 2024

We present a novel synthesis of CF 3 - and alkynyl-substituted quinoline derivatives based on Rh( iii )-catalyzed cascade reactions N -aryl amidines with two -ynones. Then, some products are transformed into polycyclic -benzo[ k ]phenanthridines through an intramolecular annulation reaction.

Язык: Английский

Процитировано

14

Synthesis of 2-Organoselenyl Quinolines via Electro-Oxidative Selenocyclization of Isocyanides DOI
Peng‐Fei Huang,

Jia-Le Fu,

Zhi-Gang Quan

и другие.

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

Опубликована: Март 12, 2025

Organoselenium compounds and quinolines are widely used in drugs materials. Herein, we report an electro-oxidative cyclization between isocyanides diselenides to effectively synthesize 2-organoselenyl a simple undivided cell without transition-metal catalysts or toxic oxidants. Gram-scale synthesis postsynthetic modifications highlighted the practicality of this electrochemical strategy. A series produced with up 82% yield, good functional group tolerance high atom efficiency under room temperature.

Язык: Английский

Процитировано

0

Multicomponent one-pot construction of benzo[f]quinoline-linked covalent organic frameworks for H2O2 photosynthesis DOI Creative Commons

Ke‐Hui Xie,

Guang-Bo Wang,

Fang Huang

и другие.

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Апрель 12, 2025

The exploration of stable and functional linkages by multicomponent reactions to enrich the stability diversity covalent organic frameworks (COFs) broaden their potential applications is fundamental significance development COFs. Herein, we report facile construction a set benzo[f]quinoline-linked COFs (B[f]QCOFs) via one-pot three-component [4 + 2] cyclic condensation aldehydes aromatic amines with easy-to-handle triethylamine as vinyl source. These B[f]QCOFs possess high crystallinity, good physico-chemical well significant light absorption ability. More importantly, obtained B[f]QCOF-1 exhibits superior H2O2 production rate 9025 μmol g-1 h-1 in pure water without any sacrificial agent under visible-light irradiation, surpassing most previously reported COF-based photocatalysts comparable conditions. This work not only provides general synthetic route for preparation fully conjugated COFs, but also helps rational design efficient photosynthesis.

Язык: Английский

Процитировано

0

Iron-catalyzed formation of six-membered rings from alkyne DOI Creative Commons
Hui Li,

Sang I. Yi,

Chunling Zeng

и другие.

Green Synthesis and Catalysis, Год журнала: 2025, Номер unknown

Опубликована: Май 1, 2025

Язык: Английский

Процитировано

0

FeCl3-Catalyzed Decyanative [4 + 2] Annulation of α-Aminonitriles with Alkynes: Access to 2,4-Diaryl Quinolines in Batch and Continuous-Flow Processes DOI

Swetha Sathyendran,

M. Kesavan,

Karthick Govindan

и другие.

Organic Letters, Год журнала: 2023, Номер 25(22), С. 4086 - 4091

Опубликована: Май 25, 2023

FeCl3-catalyzed decyanation of α-aminonitriles followed by a [4 + 2] annulation with terminal alkynes has been developed to synthesize 2,4-diaryl quinolines. A broad range aniline, aldehyde, and arylacetylene derivatives were well tolerated access quinolines in moderate good yields. The control experiment studies suggested that the reaction proceeds through nonradical pathway involving Povarov-type from situ generated iminium species. synthetic application this strategy (i) includes gram-scale synthesis (ii) continuous-flow process for few representative compounds shorter time (22 min) (iii) worked styrene as proof concept.

Язык: Английский

Процитировано

7

Cu(II)/Base Synergistic Promoted [2 + 1 + 3] Cyclization of Cyclic Ketones with α,β-Unsaturated Aldehydes/Ketones and NH4I to Access Fused Pyridines DOI
Lu Hao, Xinyu Li,

Yifeng Ou

и другие.

Organic Letters, Год журнала: 2024, Номер 26(34), С. 7191 - 7195

Опубликована: Авг. 20, 2024

Herein, a practical three-component [2 + 1 3] cyclization of various cyclic ketones with α,β-unsaturated aldehydes/ketones and ammonium iodide (NH4I) to access highly functional fused pyridines has been developed. The features this transformation include mild reaction conditions, readily available starting materials, excellent chemoselectivity. This protocol is compatible groups, the preliminary studies on mechanism are also provided.

Язык: Английский

Процитировано

2

Access to 2-thio/selenoquinolines via domino reaction of isocyanides with sulfur and selenium in water DOI
Haitao Liu,

Mengying Jia,

Shaoguang Sun

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(98), С. 14595 - 14598

Опубликована: Янв. 1, 2023

A one-pot domino reaction of o -alkenylaryl isocyanides with elemental sulfur and selenium as well FCH 2 I in water was developed for the efficient divergent synthesis 2-thio-/seleno-/fluoromethylthio-/fluoromethylseleno-quinoline derivatives.

Язык: Английский

Процитировано

4

Mg(II)‐Catalyzed [4+2] Annulation for the Synthesis of 2‐Arylquinoline Motifs: Applications and DFT Studies DOI
Tao Yang,

Yibo Qin,

Yaping Wang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 366(6), С. 1382 - 1387

Опубликована: Дек. 9, 2023

Abstract Mg‐catalyzed [4+2] cycloaddition reactions between 2‐aminobenzaldehydes and ynones offered an array of 2‐arylquinoline motifs merged with a CF 3 ‐acyl group. Furthermore, annulation as the key step, DDD107498, DDD102542, Hit analogues were assembled. Finally, computational study reaction mechanism was conducted.

Язык: Английский

Процитировано

4

Acid/base-co-catalyzed cyclization of ketones with o-amino-benzylamines: Direct synthesis of quinoline compounds DOI
Xiaoyong Zhang, Jing Chen,

Shengli Yong

и другие.

Tetrahedron Letters, Год журнала: 2023, Номер 128, С. 154700 - 154700

Опубликована: Авг. 10, 2023

Язык: Английский

Процитировано

2

Copper-Catalyzed Four-Component Domino Cyclization for the Synthesis of 2-Methylpyridines DOI
Yanfeng Ma, Tianci Xu,

Yuezhou Yuan

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 11994 - 12000

Опубликована: Авг. 17, 2024

A convenient protocol for synthesis of unsymmetrical 2-methylpyridines from acetyl ketones, ammonium salts and tertiary amines is described. The construction two C–C bonds C–N via [2 + 2 1 1] four-component domino cyclization reaction achieved using Cu(OTf) as catalyst in one pot. This shows good selectivity produces multisubstituted 2-methylpyridine derivatives yields with various functional groups.

Язык: Английский

Процитировано

0