Six-membered ring systems: pyridines and benzo derivatives DOI

Jeanese C. Badenock

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 383 - 425

Published: Jan. 1, 2023

Language: Английский

Recent Progress in Application of Propargylic Alcohols in Organic Syntheses DOI
Fatemeh Doraghi,

Amir Mohammad Mahdavian,

Somaye Karimian

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(18), P. 2991 - 3019

Published: July 14, 2023

Abstract Propargylic alcohols are readily available bifunctional (alkyne and hydroxyl groups) synthons, which recognize as one of the attractive synthetic feedstock in organic transformations. Especially, recent years employment these valuable molecules has frequently been observed literature. Hence, present review highlights advancements application propargylic cyclization, substitution, addition reactions.

Language: Английский

Citations

16

Ru(ii)-catalyzed regioselective [4 + 1] redox-neutral spirocyclization of aryl amidines with diazopyrazolones: direct access to spiro[indole-3,4′-pyrazol]-5′-ones DOI
Bo Cui,

Jian Shen,

Yadong Feng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1811 - 1816

Published: Jan. 1, 2024

An efficient protocol to construct spiro[indole-3,4′-pyrazol]-5′-ones via ruthenium( ii )-catalyzed selective C–H bond activation/[4 + 1] spirocyclization starting from easily available N -aryl amidines and diazopyrazolones has been developed.

Language: Английский

Citations

4

Synthesis of Indazole Fused 2-Benzazepines with Polarity-Dependent Fluorescence Based on Formal [4 + 3] Annulation of 3-Aryl-1H-indazoles with Cyclopropenones DOI

Qianting Zhou,

Xu Haiyun,

Chang Gao

et al.

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

Published: April 3, 2025

The effective assembly of benzazepine skeletons in a sustainable and atom-economical fashion remains challenging goal modern organic synthesis. Presented herein is novel synthesis indazole fused 2-benzazepine derivatives based on formal [4 + 3] annulation 3-aryl-1H-indazoles with cyclopropenones. formation products proceeds through Ir(III)-catalyzed aryl C-H bond metalation cyclopropenone ring-opening leading to acylation, followed by an intramolecular N-nucleophilic conjugated addition. By using this method, number valuable were effectively generated. This protocol addresses the challenges constructing medium-sized rings cascade C-H/C-C activation C-C/C-N formation. Moreover, photophysical properties thus obtained also evaluated. It turned out that all compounds tested showed solvent polarity-dependent fluorescence features, which could be potentially applied for revealing polarity their immediate environments.

Language: Английский

Citations

0

Rhodium-Catalyzed [4 + 2] Cascade Annulation to Easy Access N-Substituted Indenoisoquinolinones DOI

Xuelin Yue,

Yijie Gao,

Junwei Huang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(16), P. 2923 - 2927

Published: April 17, 2023

An efficient approach for the synthesis of N-substituted indenoisoquinolinones via rhodium(III)-catalyzed C-H bond activation/subsequent [4 + 2] cyclization starting from easily available 2-phenyloxazolines and 2-diazo-1,3-indandiones has been developed. A series indeno[1,2-c]isoquinolinones were obtained in up to 93% yield through functionalization, followed by intramolecular annulation, elimination, ring-opening a "one pot manner" under mild reaction conditions. This protocol features excellent atom- step-economy provides novel strategy chance study their biological activities.

Language: Английский

Citations

7

Rhodium(iii)-catalysed redox neutral alkylation of 3-arylbenzo[d]isoxazoles: easy access to substituted succinimides DOI

Xuelin Yue,

Xiang Zhao,

Junwei Huang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(29), P. 5985 - 5989

Published: Jan. 1, 2023

A convenient method for the alkylation of 3-arylbenzo[d]isoxazoles with maleimides under redox-neutral conditions has been developed, giving a series substituted succinimides in up to 99% yield. This transformation is highly selective give succinimides, and Heck-type products are successfully avoided. protocol features 100% atom-economy broad substrate tolerance, provides novel strategy synthesis diverse an opportunity succinylation protein medication pharmacologists discover first-in-class drugs.

Language: Английский

Citations

6

Rhodium(III)‐Catalyzed C7‐Spiroannulation of Indolines with Maleimides: Facile Access to Aza‐Spiromulticycles DOI

Jinfang Zhao,

Chao Pi, Yangjie Wu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1840 - 1846

Published: Feb. 8, 2024

Abstract Herein, we report a chemo‐ and regioselective Rh‐catalyzed redox C7‐spiroannulation reaction of N ‐benzo[ d ]imidazole indolines with maleimides, resulting in series indoline fused azaspirocycles up to 92% yield. The synthetic utility is demonstrated by the synthesis highly functionalized nitrogen‐containing spiropolycyclic skeletons. annulation could also be performed maleic esters acrylates. products were purified simple filtration. Rh catalyst can recycled, at gram‐scale using 0.5 mol% catalyst, which makes this protocol potentially applicable industry. Moreover, efficient post‐modification pharmaceutical molecules demonstrates its practicability.

Language: Английский

Citations

2

Diversity-Oriented Synthesis of Indole-Fused Polycyclic Scaffolds via Rhodium-Catalyzed NH-Indole-Directed C–H Coupling of 2-Phenyl-1H-indoles with Propargylic Alcohol Derivatives DOI

Guijiao Xiang,

Yanqiao Wang,

Leipeng Lu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(8), P. 5589 - 5605

Published: April 5, 2024

Diversity-oriented synthesis strategy for the efficient assembly of indole-fused polycyclic scaffolds via rhodium-catalyzed NH-indole-directed C–H coupling with propargylic alcohol derivatives in a regioselective manner was developed. Five 2-phenyl-1H-indole-embedded core skeletons were synthesized. In particular, three different exo-olefin-containing polycycles realized, which may be manipulated further chemistry.

Language: Английский

Citations

1

Rhodium-catalyzed formal [2 + 2 + 1] annulation of arylboronic acids with alkynes DOI
Chenhong Wang, Changhui Wu,

Yiming Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(24), P. 6915 - 6919

Published: Jan. 1, 2022

A novel rhodium-catalyzed formal [2 + 2 1] annulation of alkynes with arylboronic acids to produce 1,1-disubstituted 1( H )-indenes is developed.

Language: Английский

Citations

6

Oxidative Cyclization of Oximes with Propargyl Alcohols toward Functionalized Isoquinoline N‐Oxides Synthesis DOI
Jidan Liu,

Zhenke Yang,

Huli Long

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 13(1)

Published: Nov. 29, 2023

Abstract An efficient and regioselective synthesis of various functionalized isoquinoline N ‐oxides has been realized by Rh(III)‐catalyzed oxidative annulation aryl oximes with tertiary propargyl alcohols. The current protocol features readily available starting materials, mild reaction conditions, broad substrate scope wide functional group tolerance.

Language: Английский

Citations

3

Six-membered ring systems: pyridines and benzo derivatives DOI

Jeanese C. Badenock

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 383 - 425

Published: Jan. 1, 2023

Language: Английский

Citations

1