Theoretical Study on Ir-Catalyzed α-Amidation of 2-Acylimidazoles: Mechanism and Insertion Selectivity DOI

Juping Wang,

Zijie Lin,

Zhenjie Zheng

et al.

Organometallics, Journal Year: 2022, Volume and Issue: 41(21), P. 2942 - 2948

Published: Oct. 31, 2022

The mechanism and reactivity of Ir-catalyzed α-amidation 2-acylimidazoles have been investigated at the B3LYP-D3 level, with emphasis on nitrene insertion selectivity. calculation results show that catalytic consists iridacycle formation, CO2 release, insertion, amido protonation processes. Thereinto, is both rate- selectivity-determining steps. origin group favorably inserting into an Ir–Cα over Cγ–H bond was further unraveled. In addition, this work also explored difference between α-mono- α,α-di-substituted source identified. These meaningful insights may serve as basis for design development transition-metal-catalyzed systems featuring high

Language: Английский

Recent advances in transition metal-catalyzed transformations in N,N-disubstituted enaminones DOI
Leiqing Fu, Jie‐Ping Wan

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 130, P. 154766 - 154766

Published: Sept. 26, 2023

Language: Английский

Citations

28
Divergent Synthesis of F- and CF3-Containing N-Fused Heterocycles Enabled by Fragmentation Cycloaddition of β-CF3-1,3-Enynes with N-Aminopyridiniums Ylides DOI

Xiaotian Shi,

Qiong Wang,

Zhiqing Tang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(6), P. 1255 - 1260

Published: Feb. 7, 2024

The two novel cyclization modes of β-CF

Language: Английский

Citations

13
Transition metal- and oxidant-free [3 + 2] cyclization of azomethine imines utilizing vinylene carbonate as dual synthons DOI
Wen Li, Mengqi Zhang, Yan Jin

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(9), P. 2529 - 2533

Published: Jan. 1, 2022

A transition metal- and oxidant-free C–C/C–N annulation of azomethine imines with vinylene carbonate as dual synthons under simple reaction conditions is described herein.

Language: Английский

Citations

21
Microwave-assisted copper(i) catalyzed A3 cascade coupling of imidazo[1,2-a]pyridines via C–H bond functionalization as selective COX-2 inhibitors and antioxidants, and in silico studies DOI
Aravind R. Nesaragi, Ravindra R. Kamble, Swati R. Hoolageri

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(19), P. 9401 - 9413

Published: Jan. 1, 2023

A proficient copper( i ) catalyzed one pot synthetic protocol has been established to synthesize medicinally essential substituted imidazo[1,2- a ]pyridines via C–H bond amination followed by acetylene incorporation under microwave irradiation.

Language: Английский

Citations

13
Mechanochemical Synthesis of 1,2,4‐Triazoles via a [3+2] Cycloaddition of Azinium‐N‐Imines and Nitriles DOI
Baofu Zhu, Wen Li, Haixin Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(17), P. 2911 - 2915

Published: July 13, 2022

Abstract We report here a mechanochemical Cu‐catalyzed [3+2] cycloaddition of azinium‐ N ‐imines with nitriles under solventless grinding conditions. Various 1,2,4‐triazolos derivatives were obtained in 51–80% yields. The developed protocol offers advantages functional‐group compatibility, scalability, no use solvents, shorter reaction time, and without external heating. In addition, heterocyclic such as quinolinium isoquinolinium salts are also suitable substrates, resulting the production 1,2,4‐triazolo[1,5‐ ]quinoline 1,2,4‐triazolo[5,1‐ ]isoquinoline magnified image

Language: Английский

Citations

17
Copper-Catalyzed Formal [4 + 1] Annulation toward Diverse Trifunctionalized Indolizines from Pyridinium 1,4-Zwitterionic Thiolates and Diazos DOI
Wen Li, Hexiang Wang, Yuan Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7199 - 7207

Published: May 12, 2023

Pyridinium 1,4-zwitterionic thiolates were regarded as powerful and versatile building blocks to prepare nitrogen- sulfur-containing heterocycles. Herein, we reported a copper-catalyzed formal [4 + 1] annulation of pyridinium diazo compounds without any additives access library trifunctionalized indolizines in good yields. Besides, isoquinolinium imidazolium also applied this reaction. Of particular note is that various functional groups such -CO2R, -CO2NR2, -CF3, -CN, -(O)P(OR)2 could be easily introduced into cycloaddition products by strategy.

Language: Английский

Citations

11
Transition-metal-free [3 + 2] cycloaddition of C,N-cycloazomethylimines with in situ formed isocyanates from dioxazolones: a facile synthesis of triazolinones DOI
Lei Chen,

Peiyao Yang,

Qiuying Wang

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(6), P. 3522 - 3526

Published: Jan. 1, 2024

A novel strategy for synthesizing triazolinone with C , N -cycloazomethylimine and dioxazolone has been developed, in which the isocyanate formed situ from is employed cyclization instead of widely used -acyl nitrene.

Language: Английский

Citations

4
Iron/photoredox dual catalysis for acyl nitrene-based C–O bond formation towards phthalides DOI
Zhide Zhang,

Yangling Deng,

Ming Hou

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(98), P. 13644 - 13647

Published: Jan. 1, 2022

This paper describes iron/photoredox dual-catalyzed acyl nitrene formation and the use of in constructing various C-O bonds towards phthalides. The developed reaction starts from N-methoxyl-2-alkylbenzamides. Mechanism surveys suggest involves iron nitrene-based hydrogen atom abstraction (HAA), radical-polar crossover O-nucleophilic SN1. Distinctively, often-reported radical rebound previous publications is not observed. represents first example on synthesis Moreover, it also serves as a supplement for marketed medicines such 3-butylphthalides (NBP), thalidomide, Pomalyst Otezia.

Language: Английский

Citations

15
Microwave-Mediated, Catalyst-Free Synthesis of 1,2,4-Triazolo[1,5-a]pyridines from Enaminonitriles DOI Creative Commons

Kwanghee Lee,

Young‐Ah Kim,

Chanhyun Jung

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(4), P. 894 - 894

Published: Feb. 18, 2024

A catalyst-free, additive-free, and eco-friendly method for synthesizing 1,2,4-triazolo[1,5-a]pyridines under microwave conditions has been established. This tandem reaction involves the use of enaminonitriles benzohydrazides, a transamidation mechanism followed by nucleophilic addition with nitrile, subsequent condensation to yield target compound in short time. The methodology demonstrates broad substrate scope good functional group tolerance, resulting formation products good-to-excellent yields. Furthermore, scale-up late-stage functionalization triazolo pyridine further demonstrate its synthetic utility. plausible pathway, based on our findings, proposed.

Language: Английский

Citations

3
Five-Component [2 + 2 + 1 + 1] Tandem Benzannulation Leading to Multifunctionalized Aromatic Amines DOI
Hexiang Wang,

Shuting Li,

Xiaoying Wu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(45), P. 9648 - 9653

Published: Nov. 1, 2024

An unprecedented five-component [2 + 2 1 1] benzannulation strategy for regioselective assembly of densely functionalized aromatic amines from two ynals, malononitriles, and sodium sulfinates is established. The protocol enables the efficient installation five substituents on a benzene ring via formation multiple chemical bonds in single operation, providing various multifunctionalized primary moderate to good yields. Additionally, three-component [3 cycloaddition NH4SCN was also achieved produce 2-amnopyridine derivatives with serving as an ammonia surrogate.

Language: Английский

Citations

3