Progress in the Synthesis of Fused 1,2,3‐Triazoles

Abstract

Fused heterocycles display prodigious prominence in diverse field ranging from medicinal chemistry to material science and chemical biology to catalysis. Owing to biological importance, fused 1,2,3‐triazoles have gained much attention and hence, enormous efforts on its synthesis is given by the chemists. Diverse functionalized fused polycyclic 1,2,3‐triazole heterocycles have been designed using Huisgen's thermal intramolecular cycloaddition, copper catalyzed cycloaddition, bimetallic catalytic, greener and other miscellaneous approaches. Novel methodologies that use modified substrates such as ketones, enals, β‐keto esters, olefins, enones, C−H acids etc. in place of alkynes have been developed. Herein, synthetic methodologies to construct fused 1,2,3‐triazoles are briefly discussed.

Fused Imidazo[2,1‐b][1,2,3]triazolo[4,5‐d][1,3]thiazines: One‐Pot Synthesis, Antibiofilim, Bactericidal Effects, and in silico Studies

“…[30,33a] There are several reports on the synthesis of fused 1,2,3triazoles and their various biological activities. [34] Later, we expanded the synthetic application of the previously reported simple and effective CuI-catalyzed one pot, three-component approach [35] for the synthesis of our desired fused imidazo[2,1b] [1,2,3]triazolo [4,5-d][1,3]thiazines using 2-((3-iodoprop-2-yn-1-yl)sulfonyl)-1H-imidazole (4), which reacts with various aryl azides using the intramolecular CÀ N bond coupling reaction (Scheme 3). [36,37] As a first step, we intended to select acceptable reaction conditions using a Cu(I)-catalyzed one-pot reaction of 2-((3iodoprop-2-yn-1-yl)sulfonyl)-1H-imidazole (4) and phenyl azide ChemistrySelect at 100 °C and 120 °C temperatures in different solvents and bases.…”

“…There are several reports on the synthesis of fused 1,2,3‐triazoles and their various biological activities [34] . Later, we expanded the synthetic application of the previously reported simple and effective CuI‐catalyzed one pot, three‐component approach [35] for the synthesis of our desired fused imidazo[2,1‐ b ] [1,2,3]triazolo[4,5‐ d ][1,3]thiazines using 2‐((3‐iodoprop‐2‐yn‐1‐yl)sulfonyl)‐1H‐imidazole (4), which reacts with various aryl azides using the intramolecular C−N bond coupling reaction (Scheme 3).…”

Biomass derived Cu2O nanoparticles for N-atom insertion reactions: a base-free synthesis of quinazolinones with a green approach

“…19 Nevertheless, these reactions are only effective with volatile organic solvents or harsh solvent systems with a modest yield and lengthy reaction time. 20 In the current context, quinazolinones, a group of heterocyclic scaffolds that possess significant potential as pharmacologically active frameworks, are targeted to be produced through MCRs. These structures possess multiple functions, including but not limited to antimalarial, anticancer, anti-inflammatory, anticonvulsant, antimicrobial, antidiabetic, diuretic and antihypertensive properties (Scheme 1).…”

Syntheses and Applications of 1,2,3-Triazole-Fused Pyrazines and Pyridazines

“…Among fused heterocycles containing the more well-known fused 1,2,4-triazoles, both 1,2,4-triazolo[1,5- a ]pyrimidines [ 8 ] and 1,2,4-triazolo[4,3- a ]pyrazines [ 9 ] have been recently reviewed. Kumar and coworkers [ 10 ] surveyed 1,2,3-triazoles fused to various rings, both aromatic and non-aromatic. In the present review, we address approaches to the synthesis of 1,2,3-triazole-fused pyrazines and pyridazines and their related congeners, while setting two limitations: This review covers synthetic methods of preparing structures containing fused heterocycles 2 , 4 , 6 , 8 , 10 ( Figure 1 ).…”