Regioselective Synthesis of 1,4,5‐Trisubstituted 1,2,3‐Triazole Derivatives from α,β‐Unsaturated Carbonyls DOI
Naimish K. Verma, Smritilekha Bera,

Rajesh Gonnade

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(28)

Published: April 29, 2022

Abstract The copper‐catalyzed oxidative azide‐olefin cycloaddition (OAOC) reaction of differently substituted α , β ‐unsaturated carbonyls with azides provided an efficient method for preparing biologically active 1,4,5‐trisubstituted 1,2,3‐triazoles. In this study, the was found to be a simple and powerful constructing diverse mono‐ bis‐(1,4,5‐trisubstituted 1,2,3‐triazole) functionalized heterocyclic compounds in moderate high yields great regioselectivity. XRD‐analysis data one bis‐triazole derivatives supported regioselectivity as well conformity construction triazole nucleus. preliminary antifungal profile against C. albicans observed cinnamaldehyde‐based demonstrating promising results.

Language: Английский

Synthesis of novel immunomodulatory 1,4-disubstituted bis-1,2,3-triazoles by using click chemistry and their intracellular mechanism of action DOI
Yahya Nural,

Irem Zehra Acar,

Derya Yetkin

et al.

Bioorganic & Medicinal Chemistry Letters, Journal Year: 2022, Volume and Issue: 69, P. 128800 - 128800

Published: May 14, 2022

Language: Английский

Citations

12
Recent Strategies in Nickel-Catalyzed C–H Bond Functionalization for Nitrogen-Containing Heterocycles DOI Open Access
Ke Yang, Zhi Li,

Qingyue Hu

et al.

Catalysts, Journal Year: 2022, Volume and Issue: 12(10), P. 1163 - 1163

Published: Oct. 2, 2022

N-heterocycles are ubiquitous in natural products, pharmaceuticals, organic materials, and numerous functional molecules. Among the current synthetic approaches, transition metal-catalyzed C–H functionalization has gained considerable attention recent years due to its advantages of simplicity, high atomic economy, ready availability starting materials. In field N-heterocycle synthesis via functionalization, nickel been recognized as one most important catalysts. this review, we will introduce nickel-catalyzed intramolecular intermolecular pathways for from 2008 2021.

Language: Английский

Citations

12
PEG-mediated synthesis, antibacterial, antifungal and antioxidant studies of some new 1,3,5-trisubstituted 2-pyrazolines DOI
Sunil L. Dhonnar, Bapu S. Jagdale, Vishnu A. Adole

et al.

Molecular Diversity, Journal Year: 2022, Volume and Issue: 27(6), P. 2441 - 2452

Published: Nov. 11, 2022

Language: Английский

Citations

11
Design, Synthesis and Bioevaluation of Highly Functionalized 1,2,3-Triazole-Guanidine Conjugates as Anti-Inflammatory and Antioxidant Agents DOI

Madiha A. Siddiqui,

Amol A. Nagargoje, Mubarak H. Shaikh

et al.

Polycyclic aromatic compounds, Journal Year: 2022, Volume and Issue: 43(6), P. 5567 - 5581

Published: Aug. 8, 2022

In search of new biologically potent molecules a small focused library guanidine-1,2,3-triazole hybrid derivatives were synthesized via Organocatalytic enolate- mediated azide-carbonyl [3 + 2] cycloaddition yielding highly functionalized triazole core structure. The synthesis all the confirmed by spectral analysis 1H NMR, 13C NMR and MS. conjugates found to exhibit promising anti-inflammatory antioxidant activity. activity screened membrane stabilization method summarizes four potential 5c, 5f, 5h 5g be in comparison with standard drug Diclofenac sodium (DFS). also assessed for DPPH method. Among compounds, compounds 5d, exhibited Molecular docking study was performed gain insight into putative binding mode strength these target enzyme Cyclo-oxygenase (COX-2) enzyme. vitro silico studies together simpler designing strategy followed two-component reaction guanidine basic conditions rationalize as easily assessable novel therapeutic agents.

Language: Английский

Citations

10
1,3-Dipolar cycloaddition reactions of isatin-derived azomethine ylides for the synthesis of spirooxindole and indole-derived scaffolds: recent developments DOI

Fatemeh Rostami Miankooshki,

Mohammad Bayat, Shima Nasri

et al.

Molecular Diversity, Journal Year: 2022, Volume and Issue: 27(5), P. 2365 - 2397

Published: Aug. 4, 2022

Language: Английский

Citations

9
Azirine-triazole hybrids: selective synthesis of 5-(2H-azirin-2-yl)-, 5-(1H-pyrrol-2-yl)-1H-1,2,3-triazoles and 2-(5-(2H-azirin-2-yl)-1H-1,2,3-triazol-1-yl)pyridines DOI

Yulia V. Krivolapova,

Olesya A. Tomashenko,

Liya D. Funt

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(27), P. 5434 - 5443

Published: Jan. 1, 2022

Selective synthesis of azirine-triazole hybrids and their use in preparation pyrrole-triazole pyrrole-triazole-pyridine are reported.

Language: Английский

Citations

8
Pd-Nanoparticles-Catalyzed C(sp2)–H Arylation for the Synthesis of Functionalized Heterocycles: Recent Progress and Prospects DOI
Kapileswar Seth, Steeva Sunny, Mohit Maingle

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 56(04), P. 611 - 638

Published: March 22, 2023

Abstract Transition-metal-nanoparticles-catalyzed C–H activation/functionalization is a prominent topic in contemporary research, enabling the functionalization of privileged heterocyclic scaffolds that hold significant space scientific community due to their immense applications materials science and medicinal, natural product, agricultural chemistry. Among transition-metal-based nanoparticles, Pd nanoparticle catalysis has emerged as most attractive tool for promoting wide array practical synthetic transformations heterocycles. In last few years, catalytic application nanoparticles gained popularity generating relatively inaccessible bonds with high degree selectivity efficiency via activation surface metal atoms at nanoscale level. The quantum size effect offers large area, typically many easily accessible active sites/unit areas. These unique characteristics are considered primary factors enhanced activity compared bulk materials. catalysts anchored on solid-supports plus unsupported types (e.g., magnetic nanoparticles) allow easy separation from reaction mixture, recycling multiple times, which contributes notably sustainable management cost production process. current review, we discuss Pd-nanoparticles-catalyzed C(sp2)–H arylation synthesis functionalized heterocycles, covering literature reports 2010 2021. preparation mechanistic realizations corresponding reactions also explained briefly. 1 Introduction 2 Arylation Heterocyclic Scaffolds 2.1 Synthesis Functionalized Indole Derivatives 2.2 (Benzo)thiazole/Benzoxazole 2.3 Triazoles 2.4 Pyridines Related 2.5 Furan, Thiophene N-Methylpyrrole 2.6 Multiple Heterocycles Single-Step Strategies 3 Conclusions

Language: Английский

Citations

4
Selective Synthesis of 5‐Alkynyl Trisubstituted 1,2,3‐triazoles from Azides and Alkynes via Photoexcited Copper(I)acetylides DOI

Kesavan Prasanth,

Mandapati Bhargava Reddy, Ramasamy Anandhan

et al.

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(11)

Published: Sept. 22, 2022

Abstract Visible‐light‐initiated copper(I) catalyzed selective synthesis of 5‐alkynyl trisubstituted 1,2,3‐triazoles from azides and alkynes is reported. The reaction proceeded via photoexcited copper(I)acetylides with to in‐situ formation cuprate‐triazole followed by oxidative C−C(sp) coupling another alkynes. UV‐Visible spectrum shows that (λabs=425–485 nm) most probably the key light absorbing species responsible for CuAAC reactions.

Language: Английский

Citations

7
A Copper‐Catalyzed Interrupted Domino Reaction for the Synthesis of Fused Triazolyl Benzothiadiazine‐1‐oxides DOI Creative Commons
Renè Hommelsheim, Sandra Bausch, Arjuna Selvakumar

et al.

Chemistry - A European Journal, Journal Year: 2022, Volume and Issue: 29(13)

Published: Dec. 1, 2022

Copper(I)-catalyzed domino reactions of 2-azido sulfoximines with 1-iodoalkynes yield fused triazolyl-containing benzothiadiazine-1-oxides. The protocol features the synthesis two heterocyclic rings in one step good to excellent yields and a broad functional group tolerance. Detailed mechanistic investigations indicate that copper π-complex initiates cycloaddition oxidative C-N coupling reaction sequence. results suggest an interrupted process involving iodinated triazole as key intermediate.

Language: Английский

Citations

6
Synthesis of [1,2,3]Triazolo[1,5‐a]quinoline‐3‐carboxamides Promoted by Organocatalyst and Base DOI
Gabriel P. Costa, Gustavo B. Blödorn, Thiago Barcellos

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(30)

Published: June 25, 2023

Abstract We described here a simple and metal‐free protocol to synthesize [1,2,3]triazolo[1,5‐ ]quinoline 3‐carboxamides through two‐step synthetic strategy, in which the first step uses organocatalysis (10 mol % of diethylamine or 1,8‐diazabicyclo[5.4.0]undec‐7‐ene, while second involves use inorganic base (1.2 0.1 equiv. potassium hydroxide). These reactions were performed between β ‐keto amides o ‐carbonyl phenylazides dimethylsulfoxide as solvent at 70 °C for 2 h. The is ample, thirteen examples secondary synthesized ranging from good excellent yields (63‐96 %), six different tertiary ]quinolines obtained moderate (48–76 %).

Language: Английский

Citations

3