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

Recent Progress on Synthesis of Functionalized 1,5-Disubstituted Triazoles DOI
Manoj K. Jaiswal, Abhishek Gupta,

Faisal J. Ansari

et al.

Current Organic Synthesis, Journal Year: 2023, Volume and Issue: 21(4), P. 513 - 558

Published: April 19, 2023

Immediately after the invention of 'Click Chemistry' in 2002, regioselective 1,2,3- triazole scaffolds resulted from respective organic azides and terminal alkynes under Cu(I) catalysis have been well recognized as functional heterocyclic core at centre modern chemistry, medicinal material sciences. This CuAAC reaction has several notable features including excellent regioselectivity, high-to-excellent yields, easy to execute, short time, modular nature, mild condition, readily available starting materials, etc. Moreover, resulting triazoles can serve amide bond isosteres, a privileged group drug discovery development. More than hundreds reviews had devoted special reference 1,4-disubstituted triazoles, while only little efforts were made for an opposite regioisomer i.e., 1,5-disubstituted triazole. Herein, we presented various classical approaches expeditious synthesis wide range biologically relevant 1,5- disubstituted 1,2,3-triazole analogues. The syntheses such class diversly functionalized emerged crucial investigation domain chemistry biology. tutorial review covers literature assessment on development synthetic protocols reported during last 12 years.

Language: Английский

Citations

15

Synthesis, Cytotoxicity and Molecular Docking Studies of Chalcone Incorporated 1,2,3-Triazol-1,3,5-Triazin-Quinazoline as Anti-Cancer Agents DOI
Sujana Oggu,

Bala Divya Mallavarapu,

Pradeep Natarajan

et al.

Journal of Molecular Structure, Journal Year: 2022, Volume and Issue: 1266, P. 133412 - 133412

Published: June 3, 2022

Language: Английский

Citations

20

Design, synthesis and antimicrobial activity of novel quinoline-2-one hybrids as promising DNA gyrase and topoisomerase IV inhibitors DOI
Mohammed A. I. Elbastawesy, Fatma A. Mohamed, Islam Zaki

et al.

Journal of Molecular Structure, Journal Year: 2023, Volume and Issue: 1278, P. 134902 - 134902

Published: Jan. 3, 2023

Language: Английский

Citations

11

Three‐Component Coupling of α‐Trifluoromethyl Carbonyls, Azides and Amines for the Regioselective Synthesis of 1,4,5‐Trisubstituted 1,2,3‐Triazoles DOI
Ge Gao,

Kuantao,

Mao Mao

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(8), P. 1402 - 1408

Published: March 11, 2022

Abstract A metal‐free three‐component coupling of α‐CF 3 carbonyls, azides and amines for the regioselective synthesis 1,4,5‐trisubstituted 1,2,3‐triazoles in air is established. Various substituted 4‐amide were obtained when enolizable ketones applied aqueous reaction medium. Control 18 O‐labelling experiments revealed that situ generated β‐oxo amide was responsible formal oxygen‐shift subsequent [3+2] cycloaddition reaction, with amine as both catalyst reactant. In case non‐enolizable esters, densely functionalized 5‐amino achieved exclusively, which could enable late‐stage functionalization complex biological molecules. magnified image

Language: Английский

Citations

17

Synthesis, structural characterization and antibacterial activity evaluation of novel quinolone-1,2,3-triazole-benzimidazole hybrids DOI

Khadija El Gadali,

Meriem Rafya, Az‐Eddine El Mansouri

et al.

Journal of Molecular Structure, Journal Year: 2023, Volume and Issue: 1282, P. 135179 - 135179

Published: Feb. 16, 2023

Language: Английский

Citations

10

Stereochemical insights into functionalized triazoles: applications of NMR and quantum chemistry DOI
Л. И. Ларина, Valentin A. Semenov

Russian Chemical Reviews, Journal Year: 2025, Volume and Issue: 94(4), P. RCR5160 - RCR5160

Published: April 1, 2025

The stereochemistry of tautomeric functionalized azoles is a challenge for theoretical research, since the correct interpretation chemical behaviour and biological activity these compounds depends on understanding factors that determine structural features relative stability their tautomers. Due to physicochemical properties, 1,2,3- 1,2,4-triazoles are most promising research objects in various fields ranging from medicine, bioorganic chemistry agrochemistry materials science. This review first in-depth analysis data structure stereochemical 1,2,3-triazoles (their carbaldehydes, carbaldehydoximes, barbiturates malononitriles), model analogues, as well related compounds, obtained by combined methods based multipulse multinuclear 1H, 13C, 15N 29Si NMR spectroscopy quantum calculations. <br> bibliography includes 320 references.

Language: Английский

Citations

0

Triazole‐tethered boswellic acid derivatives against breast cancer: Synthesis, in vitro, and in‐silico studies DOI
Satya Kumar Avula, Najeeb Ur Rehman,

Faizullah Khan

et al.

Journal of Molecular Structure, Journal Year: 2023, Volume and Issue: 1282, P. 135181 - 135181

Published: Feb. 20, 2023

Language: Английский

Citations

9

Novel benzotriazole-benzimidazole metal complexes: structure-activity relationship, synthesis, characterization, and antidiabetic activity DOI
Xia Wang,

Jun-Ya Du,

Tanpeng Zhou

et al.

Journal of Molecular Structure, Journal Year: 2023, Volume and Issue: 1292, P. 136141 - 136141

Published: July 4, 2023

Language: Английский

Citations

9

Imidazole and Derivatives Drugs Synthesis: A Review DOI
Nidhi Rani, Randhir Singh, Praveen Kumar

et al.

Current Organic Synthesis, Journal Year: 2022, Volume and Issue: 20(6), P. 630 - 662

Published: Nov. 22, 2022

Imidazoles have long held a special place in heterocyclic chemistry, and their derivatives piqued interest recent years due to diverse chemistry pharmacology features. Imidazole is biologically pharmaceutically important nitrogen-containing ring. As result, researchers been interested imidazole molecules. For century half, purine, histamine, other natural compounds all contained the A number of drugs prepared marketed for treatment various diseases. In view this, we herein report detailed account synthetic procedures drugs.

Language: Английский

Citations

14

Platinum macrocatalyst for heterogeneous Si–O dehydrocoupling DOI
Konstantin V. Deriabin, Ekaterina A. Golovenko, Nikita S. Antonov

et al.

Dalton Transactions, Journal Year: 2023, Volume and Issue: 52(18), P. 5854 - 5858

Published: Jan. 1, 2023

A platinum polymer catalyst (Pt-PDMS) was synthesized by immobilization of a catalytic complex in polysiloxane chain using an azide-alkyne CuAAC cycloaddition. Insoluble Pt-PDMS can be used as effective heterogeneous macrocatalyst for Si-O dehydrocoupling. is easy to recover, purify, and reuse again catalysis.

Language: Английский

Citations

7