Novel method for the synthesis of 4-(azol-5-yl)-1,2,3-triazoles

Бакулев, В. А.; Efimov, Ilya; Belyaev, N. A.; Rozin, Yu. A.; Волкова, Н. Н.; Eltsov, Oleg S.

doi:10.1007/s10593-012-0952-z

Cited by 22 publications

(10 citation statements)

References 3 publications

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“…Mp 114-115°C. The melting point and 1 H NMR spectrum agreed with data given in the literature [6]. 2-Fluorophenylhydroxamoyl chloride (3a) (0.173 g, 1 mmol) was added to compound 2a (0.227 g, 1 mmol), followed by absolute dioxane (5 ml), and the mixture was stirred for 12 h. The reaction mixture was concentrated in vacuo, hexane was added, and the precipitate was filtered off, dried, and recrystallized from EtOH.…”

Section: Ethyl 5-[(e)-2-(dimethylamino)ethenyl]-123-thiadiazole-4-csupporting

confidence: 86%

“…The signals for the dimethylamino group of compounds 2b,c (present in the 1 H NMR spectra) were not observed in the 13 C NMR spectra due to their low intensity. We have previously observed a similar effect in the spectra of azolylenamines [5,6].…”

supporting

confidence: 67%

“…The Suzuki cross-coupling reaction is complex in experimental settings and hence has a limited use for the synthesis of 4-(azol-5-yl)isoxazoles [4]. Through systematic studies of the reactions of 3-azolylenamines [5,6] we have developed a novel, experimentally simple, and regioselective method for preparing 4-(azol-5-yl)isoxazoles by the reaction of hydroxamoyl chlorides with 3-azolylenamines. In the case of the derivatives of 1,2,3-thiadiazole, 1,2,4-oxadiazole, and isothiazole 1a-c it was found that enamines 2a-c take part in a reaction with the hydroxamoyl chlorides 3a,b in the absence of bases, to give the bicyclic compounds 6a-c in 60-67% yields.…”

mentioning

confidence: 99%

“…1 H NMR and 13 C NMR spectra were recorded on a Bruker Avance II 400 spectrometer (400 and 100 MHz, respectively) using DMSO-d 6 with TMS as internal standard. UV spectra were recorded on a Perkin-Elmer Lambda 45 spectrometer using CH 2 Cl 2 .…”

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confidence: 99%

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Novel method for the synthesis of 4-(azol-5-yl)isoxazoles

Бакулев

Efimov

Belyaev

et al. 2013

Chem Heterocycl Comp

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Section: Ethyl 5-[(e)-2-(dimethylamino)ethenyl]-123-thiadiazole-4-csupporting

confidence: 86%

supporting

confidence: 67%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Novel method for the synthesis of 4-(azol-5-yl)isoxazoles

Бакулев

Efimov

Belyaev

et al. 2013

Chem Heterocycl Comp

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“…We have turned our attention to the self‐condensation of β‐azolylenamines and their cycloaddition reactions with azides (Scheme ). This methodology was unknown before our preliminary reports were published 6e,7. The reactions of β‐azolylenamines with aryl and alkyl azides were shown to be a convenient, regioselective, and general method for the preparation of 4‐azolyl‐1,2,3‐triazoles in which these enamines are the synthetic equivalents of azolylalkynes 6e.…”

Section: Introductionmentioning

confidence: 99%

Reactions of β‐Azolylenamines with Sulfonyl Azides as an Approach to N‐Unsubstituted 1,2,3‐Triazoles and Ethene‐1,2‐diamines

et al. 2014

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The reactions of β‐azolylenamines 1 with sulfonyl azides 2 in acetonitrile furnished 1H‐4‐(azol‐5‐yl)‐1,2,3‐triazoles 3 in yields of 52–93 %. β‐Benzoylenaminones and β‐nitroenamine of type 1 also reacted with tosyl azide to form the same type of products 3, proving the generality and efficiency of the method for the synthesis of N‐unsubstituted 1,2,3‐triazoles. On the other hand, the reactions of 3‐(1‐aryl‐1,2,3‐triazol‐5‐yl)enamines with tosyl azide in the absence of a solvent afforded a mixture of (E)‐1‐dimethylamino‐2‐tosylaminoethenes 5 and N,N‐dimethyl‐N′‐tosylformamidine 6 in yields of 40–50 and 20 %, respectively. The formation of a variety of compounds from the reactions of enamines 1 with sulfonyl azides 2 is rationalized by the various possible transformations of the intermediate 5‐dimethylamino‐1,2,3‐triazolines 7.

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Metal‐Free Route for the Synthesis of 4‐Acyl‐1,2,3‐Triazoles from Readily Available Building Blocks

Thomas

Goyvaerts

Liekens

et al. 2016

Chemistry A European J

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Functionalized 1,2,3-triazole heterocycles have been known for a long time and hold an extraordinary potential in diverse research areas ranging from medicinal chemistry to material science. However, the scope of therapeutically important 1-substituted 4-acyl-1H-1,2,3-triazoles is much less explored, probably due to the lack of synthetic methodologies of good scope and practicality. Here, we describe a practical and efficient one-pot multicomponent reaction for the synthesis of α-ketotriazoles from readily available building blocks such as methyl ketones, N,N-dimethylformamide dimethyl acetal, and organic azides with 100 % regioselectivity. This reaction is enabled by the in situ formation of an enaminone intermediate followed by its 1,3-dipolar cycloaddition reaction with an organic azide. We effectively utilized the developed strategy for the derivatization of various heterocycles and natural products, a protocol which is difficult or impossible to realize by other means.

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Novel method for the synthesis of 4-(azol-5-yl)-1,2,3-triazoles

Cited by 22 publications

References 3 publications

Novel method for the synthesis of 4-(azol-5-yl)isoxazoles

Novel method for the synthesis of 4-(azol-5-yl)isoxazoles

Reactions of β‐Azolylenamines with Sulfonyl Azides as an Approach to N‐Unsubstituted 1,2,3‐Triazoles and Ethene‐1,2‐diamines

Metal‐Free Route for the Synthesis of 4‐Acyl‐1,2,3‐Triazoles from Readily Available Building Blocks

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