β-Cyclodextrin-catalyzed three-component synthesis of 4,5-disubstituted 1,2,3-(NH)-triazoles from propynals, trimethylsilyl azide and malononitrile in water

Медведева, А. С.; Демина, М. М.; Vu, Tran D.; Andreev, M. V.; Шаглаева, Н. С.; Ларина, Л. И.

doi:10.1016/j.mencom.2016.07.020

Cited by 13 publications

(3 citation statements)

References 42 publications

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“…Functionalized triazoles are used as high-energy materials, ionic liquids, dyes, universal bases in peptide nucleic acids, synthons for fine organic synthesis, and precursors for nanomaterials [9,11,13]. Such a various use of 1,2,3-triazoles requires an understanding of the features of their electronic and stereochemical structure, spectral properties, and tautomeric transitions [113][114][115][116].…”

Section: Functional 123-triazole Derivativesmentioning

confidence: 99%

“…Likewise, 4-Substituted oximes of 1,2,3-triazole-5-carbaldehyde were synthesized by the interaction of corresponding propinals, azide, and hydroxylamine in an aqueous methanol solution with microwave irradiation (Scheme 16) [114,115]: The annular prototropy of azoles, and in particular 1,2,3-triazoles, is a relatively rapid process in the timescale of NMR. Consequently, the 15 N NMR method fails to detect the signals of all of the triazolyl nitrogen atoms in the molecule of the equilibrium tautomeric mixture of 1,2,3-triazole.…”

Section: Functional 123-triazole Derivativesmentioning

confidence: 99%

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The Structure of Biologically Active Functionalized Azoles: NMR Spectroscopy and Quantum Chemistry

Ларина

2022

Magnetochemistry

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This review summarizes the data on the stereochemical structure of functionalized azoles (pyrazoles, imidazoles, triazoles, thiazoles, and benzazoles) and related compounds obtained by multipulse and multinuclear 1H, 13C, 15N NMR spectroscopy and quantum chemistry. The stereochemistry of functionalized azoles is a challenging topic of theoretical research, as the correct interpretation of their chemical behavior and biological activity depends on understanding the factors that determine the stereochemical features and relative stability of their tautomers. NMR spectroscopy, in combination with quantum chemical calculations, is the most convenient and reliable approach to the evaluation of the stereochemical behavior of, in particular, nitrogen-containing heteroaromatic and heterocyclic compounds. Over the last decade, 15N NMR spectroscopy has become almost an express method for the determination of the structure of nitrogen-containing heterocycles.

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Section: Functional 123-triazole Derivativesmentioning

confidence: 99%

Section: Functional 123-triazole Derivativesmentioning

confidence: 99%

The Structure of Biologically Active Functionalized Azoles: NMR Spectroscopy and Quantum Chemistry

Ларина

2022

Magnetochemistry

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“…In 2016, Medvedeva and coworkers demonstrated a green protocol for the selective preparation of new 4,5‐disubstituted 1 H ‐1,2,3‐triazoloalkylidenes 50 via the β‐CD (1.0 mmol)‐catalyzed three‐component reaction between substituted propynals 47 , trimethylsilyl azide (TMSN 3 ) 48, and malononitrile 49 in water at r.t. (Scheme ) …”

Section: Application Of β‐Cd For the Synthesis Of Heterocyclesmentioning

confidence: 99%

β-Cyclodextrin as an Efficient and Recyclable Supramolecular Catalyst for the Synthesis of Heterocyclic Compounds

Abbasi

2017

Journal of the Chinese Chemical Society

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β-Cyclodextrin (β-CD), a naturally occurring supramolecular structure, is an effective catalyst for the synthesis of heterocyclic compounds. Its ubiquity, high performance, nontoxicity, ease of separation, and reusability have drawn the attention of green chemists. Here we present the synthetic procedures of heterocyclic compounds catalyzed by β-CD in water and compare them with those using organic solvents. In many cases, using water as the solvent shows better efficiency than conventional organic solvents with regard to catalytic activity and simplicity of recycling procedures. This review highlights the applications of β-CD in catalysis covering the years 2004-2016.Mohsen Abbasi was born in Jam, Bushehr, Iran,in 1989. He received the B.Sc. degree in pure chemistry from the University of Zabol in 2012, and the M.Sc. degree in organic chemistry from Ferdowsi University of Mashhad, Iran, in 2014 under the supervision of Dr. Seyed Mohammad Seyedi. His research interests include organic methodology catalysis and the application of multicomponent reactions in the synthesis of heterocyclic compounds. He has co-authored several reseach papers published in reputed journals and national conference proceedings.

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Synthesis of Diverse Nitrogen Heterocycles Explored in Denitrogenative Transformations

Akter,

Anbarasan

2024

Denitrogenative Transformation of Nitrogen Heterocycles

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β-Cyclodextrin-catalyzed three-component synthesis of 4,5-disubstituted 1,2,3-(NH)-triazoles from propynals, trimethylsilyl azide and malononitrile in water

Cited by 13 publications

References 42 publications

The Structure of Biologically Active Functionalized Azoles: NMR Spectroscopy and Quantum Chemistry

The Structure of Biologically Active Functionalized Azoles: NMR Spectroscopy and Quantum Chemistry

β-Cyclodextrin as an Efficient and Recyclable Supramolecular Catalyst for the Synthesis of Heterocyclic Compounds

Synthesis of Diverse Nitrogen Heterocycles Explored in Denitrogenative Transformations

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