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

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 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

Language: 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

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 1917 - 1923

Published: Jan. 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.

Language: Английский

Citations

14

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

Jia-Le Fu,

Zhi-Gang Quan

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 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.

Language: Английский

Citations

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

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: April 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.

Language: Английский

Citations

0

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

Sang I. Yi,

Chunling Zeng

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: May 1, 2025

Language: Английский

Citations

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

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(22), P. 4086 - 4091

Published: May 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.

Language: Английский

Citations

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

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(34), P. 7191 - 7195

Published: Aug. 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.

Language: Английский

Citations

2

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

Mengying Jia,

Shaoguang Sun

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(98), P. 14595 - 14598

Published: Jan. 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.

Language: Английский

Citations

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

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(6), P. 1382 - 1387

Published: Dec. 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.

Language: Английский

Citations

4

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

Shengli Yong

et al.

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 128, P. 154700 - 154700

Published: Aug. 10, 2023

Language: Английский

Citations

2

Cascade [3 + 2] Annulation of 1,3-Dicarbonyl Compounds and Ethyl Secondary Amines for Pyrrole Synthesis via Poly C(sp3)–H Bond Functionalization DOI
Xiuli Li, Yunyun Liu, Jie‐Ping Wan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 16049 - 16054

Published: Oct. 21, 2024

The synthesis of polyfunctionalized pyrroles via the cascade reactions 1,3-dicarbonyl compounds and two molecules ethyl secondary amines has been realized simple iodine catalysis in presence Dess-Martin periodinane (DMP). formation target pyrrole products involves one new C-C C-N bonds major functionalization six C(sp

Language: Английский

Citations

0