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

Juping Wang,

Zijie Lin,

Zhenjie Zheng

и другие.

Organometallics, Год журнала: 2022, Номер 41(21), С. 2942 - 2948

Опубликована: Окт. 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

Язык: Английский

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

Tetrahedron Letters, Год журнала: 2023, Номер 130, С. 154766 - 154766

Опубликована: Сен. 26, 2023

Язык: Английский

Процитировано

29

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

и другие.

Organic Letters, Год журнала: 2024, Номер 26(6), С. 1255 - 1260

Опубликована: Фев. 7, 2024

The two novel cyclization modes of β-CF

Язык: Английский

Процитировано

14

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

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(9), С. 2529 - 2533

Опубликована: Янв. 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.

Язык: Английский

Процитировано

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

и другие.

New Journal of Chemistry, Год журнала: 2023, Номер 47(19), С. 9401 - 9413

Опубликована: Янв. 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.

Язык: Английский

Процитировано

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

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(17), С. 2911 - 2915

Опубликована: Июль 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

Язык: Английский

Процитировано

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

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(11), С. 7199 - 7207

Опубликована: Май 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.

Язык: Английский

Процитировано

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

и другие.

Green Chemistry, Год журнала: 2024, Номер 26(6), С. 3522 - 3526

Опубликована: Янв. 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.

Язык: Английский

Процитировано

4

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

Yangling Deng,

Ming Hou

и другие.

Chemical Communications, Год журнала: 2022, Номер 58(98), С. 13644 - 13647

Опубликована: Янв. 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.

Язык: Английский

Процитировано

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

и другие.

Molecules, Год журнала: 2024, Номер 29(4), С. 894 - 894

Опубликована: Фев. 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.

Язык: Английский

Процитировано

3

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

Shuting Li,

Xiaoying Wu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(45), С. 9648 - 9653

Опубликована: Ноя. 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.

Язык: Английский

Процитировано

3