Aerobic Oxidative Cycloaddition Reactions for Pyrazole Synthesis DOI

Synfacts, Journal Year: 2023, Volume and Issue: 19(05), P. 0447 - 0447

Published: April 14, 2023

Key words aerobic cycloaddition - pyrazoles copper regioselectivity

Language: Английский

N1-Allylation of Arylhydrazines via a Palladium-Catalyzed Allylic Substitution DOI
Xiaojing Wang,

Xiaoshuo Wang,

Shubing Shu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(26), P. 4880 - 4885

Published: June 22, 2023

A direct and efficient method for constructing N,N-disubstituted hydrazines via a palladium-catalyzed allylic substitution of allyl acetates with arylhydrazines as nucleophiles has been developed. This is highly selective in terms both chemo- regio-selectivity carried out under an open-air system the use DPPPy phosphine ligand. Additionally, this reaction compatible wide variety substrates, including those bearing reactive groups such Cl, Br, I, to afford various N1-allylation products moderate good yields simple mild conditions.

Language: Английский

Citations

11
Metal-Controlled Switchable Regioselective Synthesis of Substituted Imidazoles and Pyrroles via Ring Opening/Cyclocondensation with 2H-Azirines DOI
Fen Xu,

Wenjing Zhu,

Pei‐Wen Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(14), P. 9811 - 9822

Published: July 4, 2023

Catalytic selective annulation of 2H-azirines constitutes a general and modular strategy for the generation molecular complexity. By using Pd-catalyzed ring opening/heterocyclization associated with direct cleavage C–N C–C bonds under appropriate conditions, formation imidazoles is presented. Alternatively, silver-catalyzed radical [3 + 2] cycloannulation 1,3-dicarbonyl compounds provides highly functionalized pyrrole derivatives. Both aliphatic cyclic acyclic diketones are tolerated good regioselectivity. Moreover, capture experiment was carried out to determine proposed mechanism, providing support facile process.

Language: Английский

Citations

11
Palladium–Copper-Catalyzed Oxidative Intermolecular [2 + 2 + 2] Coupling–Annulation: Regioselective Synthesis of Multiaryl-Substituted Benzenes DOI
Yihan Wang,

Beining Yang,

Bo Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 4579 - 4594

Published: March 20, 2024

A palladium-catalyzed intermolecular [2 + 2 2] oxidative coupling–annulation of terminal alkenes and alkynes using copper(II) as the oxidant has been developed through direct C–C bond formation. These reactions provide effective access to multiaryl-substituted benzenes with high regioselectivity in absence any ligands. The features this protocol are broad substrate scope, atom step economy. aggregation-induced emission properties selected products were further investigated. synthesized may be worth exploring for applications fields advanced functional materials or drugs.

Language: Английский

Citations

2
Copper-Catalyzed Domino-Double Annulation of o-Aminobenzamides with 2-Iodoisothiocyanates for the Synthesis of 12H-Benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones DOI
Yingying Wu,

Beining Yang,

Yatang Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 4774 - 4783

Published: March 20, 2024

A facile and efficient copper-catalyzed domino-double annulation strategy was developed from easily accessible o-aminobenzamides 2-iodoisothiocyanates, which affords a direct pathway for the synthesis of tetracyclic fused 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones in moderate to good yields without addition ligands, bases, external oxidants. The reaction involves C–N bond cleavage formation C–N/C–S one step with advantages using an inexpensive copper catalyst easy operation. Mechanistic studies suggest that this transformation proceeds via intermolecular condensation followed by intramolecular Ullmann-type cross-coupling cyclization reaction.

Language: Английский

Citations

2
Visible-light-driven three-component annulation for the synthesis of highly functionalized 2-iminothiazolidin-4-ones without photocatalysts DOI

Beining Yang,

Yatang Wang,

Xiaojuan Yang

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(8), P. 4477 - 4483

Published: Jan. 1, 2024

A photocatalyst/base/metal-free protocol for the synthesis of fully substituted 2-iminothiazolidin-4-one derivatives at room temperature using low-energy light sources and mild reaction conditions is described.

Language: Английский

Citations

2
Synthesis of N,N‐Disubstituted Hydrazines by Electrocatalytic Addition of Hydrazines to α,β‐Unsaturated Carbonyl Compounds DOI

Qingyu Xu,

Chengwei Zhang, Hang Xu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2829 - 2834

Published: April 24, 2024

Abstract A strategy for the synthesis of N,N ‐disubstituted hydrazines via electrocatalytic addition hydrazine to α,β‐unsaturated carbonyl compounds is reported. The reaction was carried out under constant current electrolytic conditions in an undivided cell. Using this methodology, various were prepared 57–94% yield 40 minutes. By adding cyclohexanone and acetic acid mixture heating 2 hours, a one‐pot N ‐substituted indoles also developed. Furthermore, based on cyclic voltammetry control experiments, plausible mechanism involving radical pathway proposed.

Language: Английский

Citations

2
Selective N-functionalization of Arylhydrazines with Primary Alcohols and Acids under PPh3/DDQ System DOI

Shubing Shu,

Meng Yu,

Wenxin Yu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10054 - 10065

Published: July 1, 2024

We present a PPh3/DDQ-mediated regiospecific selective N-functionalization of arylhydrazines with primary benzylic alcohols and aryl carboxylic acids for the synthesis N1-benzyl N2-acyl arylhydrazines, respectively. This metal- base-free approach features very short reaction times (about 10 min), broad substrate scope, good functional group tolerance, mild conditions. Furthermore, N1-benzlated products have also been successfully applied to concise N-substituted indoles anticancer drug MDM2 inhibitor.

Language: Английский

Citations

1
Recent Highlights in the Synthesis and Biological Significance of Pyrazole Derivatives DOI Creative Commons
Ziad Moussa, Mani Ramanathan,

Shaikha Mohammad Alharmoozi

et al.

Heliyon, Journal Year: 2024, Volume and Issue: 10(20), P. e38894 - e38894

Published: Oct. 1, 2024

Language: Английский

Citations

1
Photocatalytic One-Pot Three-Component Reaction for the Regioselective Synthesis of Bromo-Substituted Pyrazoles DOI
Zhiying Zhang,

Yinyin Li,

Yatang Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16809 - 16827

Published: Nov. 1, 2024

A photocatalytic three-component cascade reaction of readily available enaminones, hydrazines, and CBr4 for the synthesis bromo-substituted pyrazoles in one pot has been demonstrated. This strategy involves intermolecular C-N/C-Br bond formation represents an efficient approach to construction 4-bromo-substituted with high regioselectivity, broad substrate scope, good functional group tolerance, convenient operation, mild conditions. Mechanistic investigations show that this proceeds via cyclization enaminones followed by a regioselective bromination using as "Br" source.

Language: Английский

Citations

1
(E)-2-Methoxyethene-1-sulfonyl fluoride as a precursor of acetylene for synthesis of C1/C2 non-functionalized pyrrolo[2,1-a]isoquinoline derivatives DOI

Jiahong Ma,

Weikang Lin, Hua‐Li Qin

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(35), P. 16332 - 16336

Published: Jan. 1, 2023

A exclusive synthesis of pyrrolo[2,1- a ]isoquinoline derivatives involving ( E )-2-methoxyethene-1-sulfonyl fluoride (MESF) and isoquinolinium N -ylides is described variety C 1 /C 2 non-functionalized ]isoquinolines were prepared.

Language: Английский

Citations

2