A Review on Chemistry and Methods of Synthesis of 1,2,4-Triazole Derivatives

被引:9
作者
Rodrigues, Searitha Couto [1 ]
de Moraes, Raphael Silva Moratorio [1 ]
Pinto, Gabriel Tavares de Almeida [1 ]
Martins, Maria Tereza Miranda [1 ]
do Nascimento, Patrick Antunes [1 ]
Soares, Deivid Lucas Alves [1 ]
Botelho, Ana Beatriz Mestre [1 ]
Cruz, Camille Cardoso [1 ]
Cunha, Anna Claudia [1 ]
机构
[1] Univ Fed Fluminense, Dept Quim Organ, Inst Quim, Programa Posgrad Quim, BR-24020141 Niteroi, RJ, Brazil
关键词
1,2,4-triazole; pharmaceutical and material science applications; synthetic methods; N-HETEROCYCLIC CARBENE; CROSS-COUPLING REACTIONS; ONE-POT SYNTHESIS; MOLECULAR DOCKING; OXIDATIVE CYCLIZATION; EFFICIENT SYNTHESIS; 3+2 CYCLOADDITION; METAL; INHIBITION; ARYL;
D O I
10.1002/tcr.202400190
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This review provides a comprehensive overview of research on 1,2,4-triazoles conducted over the last fifteen years. 1,2,4-Triazoles are highly significant in the pharmaceutical industry, with numerous compounds from this class used clinically as antifungal, antiviral, antibacterial, anti-inflammatory, and antitubercular agents. Beyond their pharmaceutical relevance, this review also explores their role in material science and agriculture. In material science, 1,2,4-triazoles are gaining prominence, particularly in the development of energetic materials (EMs), due to their exceptional properties such as thermal stability, coordination ability, and performance comparable to well-known explosives. Their applications extend to polymers, corrosion inhibitors, and metal-organic frameworks (MOFs), and they play a significant role in the development of functional materials for sensors, catalysis, and energy storage. Additionally, the review addresses general aspects and synthetic methodologies for the functionalization and construction of the 1,2,4-triazole ring. Synthetic methods discussed include metalation synthesis, cyclization of hydrazine derivatives, multicomponent reactions, cyclization of amides and amidines, and microwave-assisted synthesis. Given the significance of the triazole scaffold, its synthesis has garnered considerable attention due to its wide-ranging applications across various industrial sectors.
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页数:56
相关论文
共 153 条
[1]   Synthesis and Anti-Tubercular (Tb) Evaluation of Bis[4-Ethylidineamino[1,2,4]Triazole-3-Thiol] Tethered by 1,4-Dihydropyridine [J].
Abu-Melha, S. ;
Edrees, M. M. ;
Kheder, N. A. ;
Saad, A. M. ;
Riyadh, S. M. ;
Abdel-Aziz, M. M. ;
Abdelmoaz, M. A. ;
Gomha, S. M. .
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2022, 48 (02) :345-352
[2]   An insight on medicinal attributes of 1,2,4-triazoles [J].
Aggarwal, Ranjana ;
Sumran, Garima .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2020, 205
[3]   ISOMERIC AND NUCLEAR-SUBSTITUTED BETA-AMINOETHYL-1,2,4-TRIAZOLES [J].
AINSWORTH, C ;
JONES, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (03) :621-624
[4]   Design, synthesis and mechanistic study of new 1,2,4-triazole derivatives as antimicrobial agents [J].
Amin, Noha H. ;
El-Saadi, Mohamed T. ;
Ibrahim, Ahmed A. ;
Abdel-Rahman, Hamdy M. .
BIOORGANIC CHEMISTRY, 2021, 111
[5]   Inhibition of Brass (80/20) by 5-Mercaptopentyl-3-Amino-1,2,4-Triazole in Neutral Solutions [J].
Arkhipushkin, Ivan A. ;
Shikhaliev, Khidmet S. ;
Potapov, Andrei Y. ;
Sapronova, Lyudmila V. ;
Kazansky, Leonid P. .
METALS, 2017, 7 (11)
[6]   Palladium N-heterocyclic carbene complexes for the Mizoroki-Heck reaction: An appraisal [J].
Balinge, Kamlesh Rudreshwar ;
Bhagat, Pundlik Rambhau .
COMPTES RENDUS CHIMIE, 2017, 20 (07) :773-804
[7]   Cu-Catalyzed Aerobic Oxidative Cyclization of Guanidylpyridines and Derivatives [J].
Bartels, Bjoern ;
Bolas, Conor Gordon ;
Cueni, Philipp ;
Fantasia, Serena ;
Gaeng, Nicolas ;
Trita, Andrada Stefania .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02) :1249-1257
[8]   One-Pot Synthesis of 3,4,5-Trisubstituted 1,2,4-Triazoles via the Addition of Hydrazides to Activated Secondary Amides [J].
Bechara, William S. ;
Khazhieva, Inna S. ;
Rodriguez, Elsa ;
Charette, Andre B. .
ORGANIC LETTERS, 2015, 17 (05) :1184-1187
[9]  
Bladin J.A., 1885, Ber. Dtsch. Chem. Ges, V18, P1544, DOI [10.1002/cber.188501801335, DOI 10.1002/CBER.188501801335]
[10]   Preparation and thermal stability of optically active 1,2,4-triazolium-based ionic liquids [J].
Borowiecki, Pawel ;
Poterala, Marcin ;
Maurin, Jan ;
Wielechowska, Monika ;
Plenkiewicz, Jan .
ARKIVOC, 2012, :262-281