A CO2-Catalyzed Transamidation Reaction DOI
Yang Yang, Jian Liu, Fadhil S. Kamounah

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(23), P. 16867 - 16881

Published: Nov. 1, 2021

Transamidation reactions are often mediated by reactive substrates in the presence of overstoichiometric activating reagents and/or transition metal catalysts. Here we report use CO2 as a traceless catalyst: catalytic amounts CO2, transamidation were accelerated with primary, secondary, and tertiary amide donors. Various amine nucleophiles including amino acid derivatives tolerated, showcasing utility peptide modification polymer degradation (e.g., Nylon-6,6). In particular, N,O-dimethylhydroxyl amides (Weinreb amides) displayed distinct reactivity CO2-catalyzed versus N2 atmosphere. Comparative Hammett studies kinetic analysis conducted to elucidate activation mechanism molecular which was supported DFT calculations. We attributed positive effect reaction stabilization tetrahedral intermediates covalent binding electrophilic CO2.

Language: Английский

TBAI‐Promoted Electrochemical Cyclization: Synthesis of Quinazolines Using Cascade C—N Bond Generation DOI Open Access
Kamal Kant, Priyadarshini Naik,

Yaqoob A. Teli

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(1)

Published: Jan. 1, 2025

Abstract An electrochemical cyclization strategy is employed herewith for the eco‐friendly and cost‐effective synthesis of 2‐substituted quinazolines by using 2‐aminobenzylamines aldehydes or alcohols as starting substrates. The reactions were conducted under two distinct reaction temperatures: 25 °C 60 alcohols. Tetra‐ n ‐butylammonium iodide (TBAI) participates in dual roles such as, an electrolyte a mild reagent to facilitate formation at constant current 30 mA graphite electrode anode platinum cathode dimethyl sulfoxide (DMSO) solvent. Under devised process, accomplished with broad substrate scope excellent yields (up 90%), which reduces toxic side products. plausible mechanistic pathways have been formulated, are supported control experiments cyclic voltammetry studies. findings demonstrate that conditions, iodonium ions generated, play crucial role enhancing efficacy described method.

Language: Английский

Citations

2
Pyrrolo[2,1-a]isoquinoline scaffolds for developing anti-cancer agents DOI Creative Commons
Leidy J. García Maza, Arturo René Mendoza Salgado, Vladímir V. Kouznetsov

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(3), P. 1710 - 1728

Published: Jan. 1, 2024

Fused pyrrolo[2,1- a ]isoquinolines have emerged as compelling molecules with remarkably potent cytotoxic activity and topoisomerase inhibitors.

Language: Английский

Citations

9
Electrochemical Cyclization–Desulfurization Approach for the Synthesis of 1,3-Benzoxazines Using Cascade C–O and C–N Bond Formation DOI
Kamal Kant, Priyadarshini Naik, Chandresh K. Patel

et al.

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

Published: Jan. 29, 2025

A cost-effective, eco-friendly, and highly efficient one-pot electrochemical process has been described for the synthesis of 4H-1,3-benzoxazine 4,5-dihydro-1,3-benzoxazepine derivatives by employing 2-aminobenzyl alcohols, 2-(2-aminophenyl)ethan-1-ol, isothiocyanate derivatives, TBAPF6 as an electrolyte. The developed method is accomplished at 25 °C with a constant current 20 mA. Utilizing graphite anode platinum cathode in dimethyl sulfoxide solvent, devised metal-free approach minimizes production waste eliminates need external oxidizing agents. Furthermore, these valuable molecules significantly enhances ongoing trends synthetic organic chemistry.

Language: Английский

Citations

1
Ruthenaelectro‐Catalyzed Domino Three‐Component Alkyne Annulation for Expedient Isoquinoline Assembly DOI Creative Commons
Xuefeng Tan, Xiaoyan Hou, Torben Rogge

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 60(9), P. 4619 - 4624

Published: Dec. 3, 2020

Abstract The electrochemical three‐component assembly of isoquinolines has been accomplished by ruthenaelectro‐catalyzed C−H/N−H functionalization. robustness the electrocatalysis was reflected an ample substrate scope, efficient electrooxidation, and operationally friendly procedure. isolation key intermediates detailed mechanistic studies, including unprecedented cyclovoltammetric analysis a seven‐membered ruthenacycle, provided support for unusual ruthenium(II/III/I) regime.

Language: Английский

Citations

61
Isocyanide-Based Multicomponent Reactions in Water: Advanced Green Tools for the Synthesis of Heterocyclic Compounds DOI

Tahereh Nasiriani,

Siamak Javanbakht, Mohammad Taghi Nazeri

et al.

Topics in Current Chemistry, Journal Year: 2022, Volume and Issue: 380(6)

Published: Sept. 22, 2022

Language: Английский

Citations

32
NRF2 Activation by Nitrogen Heterocycles: A Review DOI Creative Commons
Melford C. Egbujor, Paolo Tucci,

Ugomma C. Onyeije

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(6), P. 2751 - 2751

Published: March 18, 2023

Several nitrogen heterocyclic analogues have been applied to clinical practice, and about 75% of drugs approved by the FDA contain at least a moiety. Thus, heterocycles are beneficial scaffolds that occupy central position in development new drugs. The fact certain compounds significantly activate NRF2/ARE signaling pathway upregulate expression NRF2-dependent genes, especially HO-1 NQO1, underscores need study roles pharmacological effects N-based moieties NRF2 activation. Furthermore, exhibit significant antioxidant anti-inflammatory activities. NRF2-activating molecules tremendous research interest recent times due their therapeutic neuroinflammation oxidative stress-mediated diseases. A comprehensive review NRF2-inducing activities derivatives will broaden prospects wide range present review, as first its kind, provides an overview activation underpinning actions several diseases, properties structural–activity relationship also discussed with aim making discoveries stimulate innovative this area.

Language: Английский

Citations

21
Recent Advancements in Strategies for the Synthesis of Imidazoles, Thiazoles, Oxazoles, and Benzimidazoles DOI
Kamal Kant, Chandresh K. Patel, Sourav Banerjee

et al.

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(47)

Published: Dec. 13, 2023

Abstract Nitrogen‐containing heterocycles such as imidazoles, thiazoles, and oxazoles play a significant role in the fields of biological pharmaceutical chemistry. These compounds were widely used for agrochemical, pesticide, medicinal, industrial applications. Due to wide spectrum structural diversity well activity N ‐heterocycles, plethora reports on their synthesis have appeared last few decades. However, developments various bond‐forming strategies C−C, C−N, C−O, C−S, N−N, C−H activation, been powerful synthetic tool derive copious ‐heterocycles. The most prominent fascinating imidazole, thiazole, oxazoles, benzimidazole moieties by C−C C−N coupling reactions, multi‐component cycloaddition etc. are discussed this study. studies demonstrated enormous potential methods accelerating modern chemical establishing molecular beauty through bonding. aspects methodologies, like optimized conditions, substrate scope, mechanistic investigations, detail.

Language: Английский

Citations

19
Copper‐Catalyzed C(sp3)− Functionalization and Annulation of 2‐Bromoaryl Oximes with Active Methylene Compounds towards Synthesis of Isoquinoline N‐Oxides DOI
Chandresh K. Patel, Raghuram Gujjarappa, Kamal Kant

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(13), P. 2203 - 2210

Published: June 9, 2023

Abstract The established process proceeds through copper (II)‐catalyzed C( sp 3 )− functionalization of β ‐diketones/ ‐ketoesters with 2‐bromobenzaldehyde oximes followed by the intramolecular cyclization in situ generated acylated intermediates to deliver isoquinoline N ‐oxides. copper(II) acetate catalyzed C−H showed maximum efficacy at 60 °C methanol/toluene as solvent. described reaction conditions were applicable over a wide range substrates variety functional groups yield ‐oxides yields up 85%. developed approach was further elucidated means control experiments and DFT calculations.

Language: Английский

Citations

17
Super-Electron-Donor 2-Azaallyl Anions Enable Construction of Isoquinolines DOI

Quan‐Xing Zi,

Minyan Li,

Jielun Cong

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(9), P. 1786 - 1790

Published: Feb. 25, 2022

Herein is introduced the application of "super-electron-donor"(SED) 2-azaallyl anions in a tandem reduction/radical cyclization/radical coupling/aromatization protocol that enables rapid construction isoquinolines. The value this transition-metal-free method highlighted by wide range isoquinoline ethyl amines prepared with good functional group tolerance and yields. An operationally simple gram scale synthesis also conducted, confirming scalability.

Language: Английский

Citations

22
Rh(III)-Catalyzed Defluorinative [4 + 2] Annulation of N-Sulfonylarylamides with Ethyl 2-Diazo-3,3,3-trifluoropropanoate: Synthesis of 1,3,4-Functionalized Isoquinolines DOI
Haosheng Li,

Mingjing Mei,

Lei Zhou

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(49), P. 8969 - 8974

Published: Dec. 1, 2022

Using 2-diazo-3,3,3-trifluoropropanoate as a nontraditional two-carbon reaction partner, Rh(III)-catalyzed defluorinative [4 + 2] annulation for the synthesis of 1,3,4-functionalized isoquinolines was developed. The proceeds by sequential C-H carbenoid insertion, dual C-F bond cleavage/annulation, and N- to O-sulfonyl migration. resultant products were converted diverse 1,3,4-trisubstituted based on functionalization newly installed 1-sulfonate, 2-fluoro functional handles, and/or remaining ester motif.

Language: Английский

Citations

19