I<sub>2</sub>-Mediated Oxidative C–N and N–S Bond Formation in Water: A Metal-Free Synthesis of 4,5-Disubstituted/N-Fused 3-Amino-1,2,4-triazoles and 3-Substituted 5-Amino-1,2,4-thiadiazoles

Jatangi, Nagesh; Nagaraju, Tumula; Palakodety, Radha Krishna; Nakka, Mangarao

doi:10.1021/acs.joc.8b00753

Cited by 48 publications

(16 citation statements)

References 43 publications

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“…Surprisingly, when 2-hydrazinylpyridine was employed in the reaction, the desired product 6o was obtained only in a 10% yield. In this case, 2-hydrazinylpyridine reacted directly with phenyl isothiocyanate to form N -phenyl-[1,2,4]triazolo[4,3- a ]pyridin-3-amine 6o′ . Unfortunately, the alkyl hydrazines failed in this reaction, and only a trace amount of 6p was observed.…”

Section: Resultsmentioning

confidence: 99%

Metal- and Oxidant-Free Green Three-Component Desulfurization and Deamination Condensation Approach to Fully Substituted 1H-1,2,4-Triazol-3-amines and Their Photophysical Properties

et al. 2021

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A metal-and oxidant-free three-component desulfurization and deamination condensation of amidines, isothiocyanates, and hydrazines for the synthesis of structurally diverse fully substituted 1H-1,2,4-triazol-3-amines is described. The reaction proceeds without the requirement of any external catalysts, metals, ligands, or oxidants. This [2 + 1 + 2] cyclization strategy involves C−N and C−S bond cleavage and the formation of new C−N bonds in one pot. This transformation provides a series of full substituted 1H-1,2,4-triazol-3-amines with advantages of a broad substrates scope, mild reaction conditions, environmental friendliness, and easy gram-scale applications. The fluorescence and aggregation-induced emission (AIE) properties of selected products were further tested. These synthesized 1H-1,2,4-triazol-3-amines may be worth investigating for further applications in the fields of organic chemistry, medicinal chemistry, and optical materials.

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Section: Resultsmentioning

confidence: 99%

Metal- and Oxidant-Free Green Three-Component Desulfurization and Deamination Condensation Approach to Fully Substituted 1H-1,2,4-Triazol-3-amines and Their Photophysical Properties

et al. 2021

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“…I 2 -mediated oxidative N-S and C-N bond formations are an ecologically friendly and effective approach for synthesizing novel 1,2,4-triazoles from isothiocyanates ( Scheme 4 ) [ 35 ].…”

Section: Synthesis Of 124-triazolesmentioning

confidence: 99%

Novel 1, 2, 4-Triazoles as Antifungal Agents

Kazeminejad

Marzi

Shiroudi

et al. 2022

BioMed Research International

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The development of innovative antifungal agents is essential. Some fungicidal agents are no longer effective due to resistance development, various side effects, and high toxicity. Therefore, the synthesis and development of some new antifungal agents are necessary. 1,2,4-Triazole is one of the most essential pharmacophore systems between five-membered heterocycles. The structure-activity relationship (SAR) of this nitrogen-containing heterocyclic compound showed potential antifungal activity. The 1,2,4-triazole core is present as the nucleus in a variety of antifungal drug categories. The most potent and broad activity of triazoles have confirmed them as pharmacologically significant moieties. The goal of this review is to highlight recent developments in the synthesis and SAR study of 1,2,4-triazole as a potential fungicidal compound. In this study, we provide the results of a biological activity evaluation using various structures and figures. Literature investigation showed that 1, 2, 4-triazole derivatives reveal the extensive span of antifungal activity. This review will assist researchers in the development of new potential antifungal drug candidates with high effectiveness and selectivity.

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“…Nakka et al developed molecular iodine mediated convenient approach for the synthesis substituted 1,2,4-triazoles (20.3, 20.5) and 1,2,4-thiadiazoles 20.7 from isothiocyanates 20.1 in good to excellent yields in an aqueous medium (Scheme 20). [93] At first, isothiocyanate derivatives 20.1 reacted with compounds 20.…”

Section: Cà N Bond Forming Reactionsmentioning

confidence: 99%

Iodine‐Catalyzed or ‐Mediated Reactions in Aqueous Medium

Samanta¹

2021

Asian J Org Chem

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Transition metal‐catalyzed reactions are the heart of modern organic synthetic chemistry. In most cases, the synthesis of target molecules involved at least one or more transition metals such as palladium, ruthenium, rhodium, platinum, iridium, rhenium, cobalt, copper, iron, etc. But these transition metals are costly, toxic, and sometimes very difficult to separate from the target product. Instead of transition metals, molecular iodine or iodide salts have drawn the attention of modern organic synthetic chemists over a few decades due to their inexpensiveness, tolerance, and environmentally benign nature. So molecular iodine or iodide catalyzed reactions are highly efficient, atom‐economical, easy to control, eco‐ friendly protocol rather than transition metal‐catalyzed reactions. But many iodine‐catalyzed or mediated reactions, toxic solvents like tetrahydrofuran (THF), 1,4 dioxane, dimethylacetamide (DMA), dimethylformamide (DMF), benzene, toluene, chlorobenzene, nitrobenzene, n‐hexane, etc. are used which is a major concern in terms of environmental issues. Therefore, our present endeavour focuses on the recent developments (mainly in the period 2005–2020) of the iodine‐catalyzed or iodine‐mediated various reactions like oxidative additions, condensation reactions, C−C, C−N, C−O, C−S cross‐couplings etc. consciously performed in an aqueous medium to avoid environmental hazardous, which is a thrust area to the young researchers.

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I₂-Mediated Oxidative C–N and N–S Bond Formation in Water: A Metal-Free Synthesis of 4,5-Disubstituted/N-Fused 3-Amino-1,2,4-triazoles and 3-Substituted 5-Amino-1,2,4-thiadiazoles

Cited by 48 publications

References 43 publications

Metal- and Oxidant-Free Green Three-Component Desulfurization and Deamination Condensation Approach to Fully Substituted 1H-1,2,4-Triazol-3-amines and Their Photophysical Properties

Metal- and Oxidant-Free Green Three-Component Desulfurization and Deamination Condensation Approach to Fully Substituted 1H-1,2,4-Triazol-3-amines and Their Photophysical Properties

Novel 1, 2, 4-Triazoles as Antifungal Agents

Iodine‐Catalyzed or ‐Mediated Reactions in Aqueous Medium

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I2-Mediated Oxidative C–N and N–S Bond Formation in Water: A Metal-Free Synthesis of 4,5-Disubstituted/N-Fused 3-Amino-1,2,4-triazoles and 3-Substituted 5-Amino-1,2,4-thiadiazoles

Cited by 48 publications

References 43 publications

Metal- and Oxidant-Free Green Three-Component Desulfurization and Deamination Condensation Approach to Fully Substituted 1H-1,2,4-Triazol-3-amines and Their Photophysical Properties

Metal- and Oxidant-Free Green Three-Component Desulfurization and Deamination Condensation Approach to Fully Substituted 1H-1,2,4-Triazol-3-amines and Their Photophysical Properties

Novel 1, 2, 4-Triazoles as Antifungal Agents

Iodine‐Catalyzed or ‐Mediated Reactions in Aqueous Medium

Contact Info

Product

Resources

About

I₂-Mediated Oxidative C–N and N–S Bond Formation in Water: A Metal-Free Synthesis of 4,5-Disubstituted/N-Fused 3-Amino-1,2,4-triazoles and 3-Substituted 5-Amino-1,2,4-thiadiazoles