Reactivity of 1,2,3-triazoles towards sulfonyl chlorides. A novel approach to 1- and 2-sulfonyl-4-azolyl-1,2,3-triazoles

Beryozkina, Tetyana; Efimov, Ilya; Fabian, Walter M. F.; Беляев, Николай А.; Слепухин, П. А.; Исенов, Максим Л.; Dehaen, Wim; Lübec, Gert; Eltsov, Oleg S.; Fan, Zhijin; Thomas, Joice; Бакулев, В. А.

doi:10.1016/j.tet.2015.06.088

Cited by 20 publications

(9 citation statements)

References 44 publications

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“…In order to obtain 1-sulfonyl-1,2,3-triazoles used in the reaction, cycloalkeno-, dihydropyrano-, and dihydronaphtho- NH -1,2,3-triazoles were treated with sulfonyl chlorides according to the synthesis of monocyclic 1-sulfonyl-1,2,3-triazoles developed earlier in our laboratory . Isomeric N -2-substituted sulfonyl triazoles were also formed in trace amounts along with N -1-sulfonyl-1,2,3-triazoles under these conditions.…”

Section: Resultsmentioning

confidence: 99%

Rhodium-Catalyzed Transannulation of 4,5-Fused 1-Sulfonyl-1,2,3-triazoles with Nitriles. The Selective Formation of 1-Sulfonyl-4,5-fused Imidazoles versus Secondary C–H Bond Migration

et al. 2022

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The reactivity of readily available 4,5-fused-1-sulfonyl-1,2,3-triazoles was examined in the Rh(II)-catalyzed transannulation reaction with nitriles. We have come across the interesting observation that 1-sulfonyl cycloalkeno[d][1,2,3]triazoles that possess β-hydrogens resist intramolecular β-hydride migration and could serve as a new source of Rh-iminocarbenoids for intermolecular Rh(II)-catalyzed transannulation reactions. As a result, 1-sulfonyl cyclohexeno-, cyclohepteno-, dihydropyrano-, 5-phenyltetrahydrobenzo-, and 4,5-dihydronaphtho[d]imidazoles were synthesized from various nitriles in good yields. A one-pot methodology has also been executed for the synthesis of NH-imidazoles.

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Section: Resultsmentioning

confidence: 99%

Rhodium-Catalyzed Transannulation of 4,5-Fused 1-Sulfonyl-1,2,3-triazoles with Nitriles. The Selective Formation of 1-Sulfonyl-4,5-fused Imidazoles versus Secondary C–H Bond Migration

et al. 2022

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“…Generally, N -sulfonyl-1,2,3-triazoles 6.2 could be synthesized via the sulfonylation of corresponding N -H-1,2,3-triazoles 6.1 with sulfonyl chlorides (Scheme ). However, the formation of mixtures of products 6.2 and 6.3 is major drawback that significantly reduces the efficiency and applicability . Alternatively, CuAAC has emerged as the most effective and reliable click reaction, giving facile access to a wide range of 1,4-disubstituted triazoles 6.6 from terminal alkynes 6.4 and azides 6.5 (Scheme ).…”

Section: Synthesis Of 123-triazolesmentioning

confidence: 99%

“…However, the formation of mixtures of products 6.2 and 6.3 is major drawback that significantly reduces the efficiency and applicability. 40 Alternatively, CuAAC has emerged as the most effective and reliable click reaction, giving facile access to a wide range of 1,4disubstituted triazoles 6.6 from terminal alkynes 6.4 and azides 6.5 (Scheme 6). 41,42 The efficiency of this reaction relies on its significantly high regioselectivity and its high yields compared with the traditional Huisgen cycloaddition.…”

Section: Synthesis Of 123-triazolesmentioning

confidence: 99%

1,2,3-Triazole and Its Analogues: New Surrogates for Diazo Compounds

2022

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Readily accessible and shelf-stable 1,2,3-triazole and its analogues such as pyridotriazole, triazoloindole, benzotriazole, and thiadiazole exist in equilibrium with their ring-opened isomers, viz., diazo compounds. These ring-opened isomers could be trapped by various metal catalysts (e.g., Rh, Pd, Cu, Co, Ag, etc.) to generate the corresponding metal carbenoids with extrusion of nitrogen. As a consequence, these unique N-heterocycles facilitate access to a realm of N-containing complex structural motifs of biological importance through denitrogenative transformations such as transannulations, insertions, ylide formation, and rearrangements by trapping of the metal carbenoids with a diverse range of coupling partners (e.g., alkenes, alkynes, nitriles, carbo/heterocycles, X–H/C–X bonds, etc.). Hence, suitably substituted triazole derivatives have emerged as efficient surrogates of diazo compounds for the generation of reactive metal carbenoids during the past decades. In this comprehensive review, we aim to discuss in detail the remarkable advancement in their synthesis and synthetic applications.

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“…Since the beginning of this millennium, 1,2,3‐triazoles have become very fashionable and rather available compounds due to the landmark discovery of copper catalyzed alkyne azide cycloaddition (CuAAC) giving access to various types of 1,2,3‐triazoles and facilitating their use in medicinal chemistry, in organic synthesis as building blocks, in chemical biology, and in material chemistry Apart from the CuAAC reaction, the transformation of functionalized hydrazones, the reactions of azides with enamines, and carbonyl active methylene compounds,, reactions of NH‐1,2,3‐triazoles with electrophiles,, intra‐ and intermolecular reactions of diazo compounds with aldimines, and transformations of other heterocyclic compounds are the main synthetic methods towards 1,2,3‐triazoles of various structures. However, these methods are not applicable to the synthesis of 1,2,3‐triazoles bearing both sulfonylamido and amidino groups which are of interest for medicinal chemistry .…”

Section: Introductionmentioning

confidence: 99%

A Base‐Controlled Reaction of 2‐Cyanoacetamidines (3,3‐Diaminoacrylonitriles) with Sulfonyl Azides as a Route to Nonaromatic 4‐Methylene‐1,2,3‐triazole‐5‐imines

et al. 2020

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Reactions of 2‐cyanoacetamidines with sulfonyl azides were shown to take place via two different pathways to form a mixture of 1‐substituted 5‐amino‐1,2,3‐triazoles 3 and novel 4‐methylene‐1H‐1,2,3‐triazole‐5(4H)‐imine derivatives 4–14. In the absence of a base, 5‐amino‐1,2,3‐triazoles 3 are formed as the only products. The presence of 1.2 equiv. of sodium ethoxide or DBU switches the reaction outcome while involving the cyano group, resulting (after a 1,5‐protic shift) in triazoles 4–14 as the only products. The methods were elaborated for the selective and efficient synthesis of triazoles 3 and 4‐methylene‐1,2,3‐triazole‐5‐imines 4–14 including one‐pot synthesis from sodium azide and sulfonyl chlorides. The unusual structure of 4–14 compounds was confirmed by X‐ray data and 2D 1H–15N and 1H–13C NMR spectra. The formation of the products was explained by the presence of two strong hydrogen bonds N···H and O···H in these molecules.

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Reactivity of 1,2,3-triazoles towards sulfonyl chlorides. A novel approach to 1- and 2-sulfonyl-4-azolyl-1,2,3-triazoles

Cited by 20 publications

References 44 publications

Rhodium-Catalyzed Transannulation of 4,5-Fused 1-Sulfonyl-1,2,3-triazoles with Nitriles. The Selective Formation of 1-Sulfonyl-4,5-fused Imidazoles versus Secondary C–H Bond Migration

Rhodium-Catalyzed Transannulation of 4,5-Fused 1-Sulfonyl-1,2,3-triazoles with Nitriles. The Selective Formation of 1-Sulfonyl-4,5-fused Imidazoles versus Secondary C–H Bond Migration

1,2,3-Triazole and Its Analogues: New Surrogates for Diazo Compounds

A Base‐Controlled Reaction of 2‐Cyanoacetamidines (3,3‐Diaminoacrylonitriles) with Sulfonyl Azides as a Route to Nonaromatic 4‐Methylene‐1,2,3‐triazole‐5‐imines

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