An expedient approach to substituted triazolo[1,5-a][1,4]benzodiazepines via Cu-catalyzed tandem Ullmann C–N coupling/azide-alkyne cycloaddition

Majumdar, K. C.; Ganai, Sintu

doi:10.1016/j.tetlet.2013.08.125

Cited by 39 publications

(18 citation statements)

References 47 publications

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“…20 Copper catalyzed tandem Ullmann C-N coupling followed by azide-alkyne cycloaddition approach has been described by Majumdar and co-worker. 21 Eycken group have reported Cu-catalyzed azidation-cyclization reaction for the synthesis of fused triazoles. 22 Although the above mentioned method is efficient, it is limited to the aliphatic substituents at C3-position and it requires metal-catalyst.…”

Section: Introductionmentioning

confidence: 99%

An expedient route to highly diversified [1,2,3]triazolo[1,5-a][1,4]benzodiazepines and their evaluation for antimicrobial, antiproliferative and in silico studies

et al. 2015

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An efficient diversity oriented synthesis of [1,2,3]triazolo[1,5-a][1,4]benzodiazepines has been developed by sequential diazotization, azidation and cycloaddition reactions in a onepot fashion. This strategy allows an easy accessibility of triazole fused [1,4]benzodiazepines in good yields. The main objective of this methodology is to introduce various substituents at all possible positions under mild reaction conditions. All the synthesized compounds were evaluated for their antimicrobial, anticancer and in silico activity. Among the tested compounds (2a-n), the derivatives 2a, 2b, 2d, 2k, 2g, 2j, 2m and 2l have displayed broad spectrum of antibacterial activity. Anticancer activity results revealed that compounds 2a, 2g and 2m exhibited potent in vitro anticancer activity against A549 lung adenocarcinoma cancer cell line. Further, molecular docking studies of all the synthesized compounds were performed to gain a comprehensive understanding of the plausible binding modes and also to compare the theoretical and experimental results of these compounds.

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Section: Introductionmentioning

confidence: 99%

An expedient route to highly diversified [1,2,3]triazolo[1,5-a][1,4]benzodiazepines and their evaluation for antimicrobial, antiproliferative and in silico studies

et al. 2015

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“…Not only does this allow CuAAC reactions to be employed in a diverse range of chemical environments, but it also facilitates the development of tandem reactions around this bond forming process. 5 Examples include substitution, 6–8 desilylation, 9,10 decarboxylation, 11 cross-coupling, 12 oxidation, 13 and condensation, 14 along with combinations thereof. Establishing reliable tandem CuAAC methods enables the efficient preparation of 1,2,3-triazole-containing molecules, which have shown value in diverse fields including coordination compounds, 15–17 chemosensors, 18 bioimaging agents, 17,19 and polymeric materials.…”

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confidence: 99%

Tandem synthesis of 1-formyl-1,2,3-triazoles

Fletcher

Christensen

Villa

2017

Tetrahedron Letters

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A tandem method for preparing 4-formyl-1,2,3-triazoles via a two-step one-pot acetal cleavage/CuAAC reaction was developed. Using this method, 4-formyl-1,2,3-triazole analogs with both electron-withdrawing and electron-donating substituents were prepared in good yield and purity. Expansion of this method to a three-step tandem reaction that incorporates an additional step of azide substitution was also successful, circumventing the need for organic azide isolation. This one-pot method, noteworthy in its simplicity and mild conditions, utilizes practical, readily available reactants and relies on protic solvent to promote acid-catalyzed acetal cleavage.

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“…For example, multi‐step reductive annulation of 2‐nitrobenzoic acids (using SnCl 2 or Fe as the reducing reagents) [4] or 2‐aminobenzoate esters [5] with isonitriles amines and 1,2‐dicarbonyl compounds or acids could afford 3 H ‐benzo[e][1,4](4 H )‐ones (Scheme 1A). Cu‐catalyzed tandem Ullmann C−N coupling of 2 ‐ azidobenzylic halides with propargylic amines [6] or reductive coupling [using NaBH(OAc) 3 as the reducing reagent] of 2 ‐ azidobenzaldehydes/2 ‐ azidoacetophenones with propargylic amines [7] followed by intramolecular click reactions of the corresponding intermediates could afford triazolo[1,5‐a][1,4](Scheme 1B). Base‐mediated coupling of 2‐aminobenzamides with o ‐dihalobenzenes could afford 5 H ‐dibenzo[b,e][1,4]diazepin‐11(10 H )‐ones (Scheme 1C) [8] .…”

Section: Methodsmentioning

confidence: 99%

Efficient Construction of 5H‐1,4‐Benzodiazepine Derivatives by a Catalyst‐Free Direct Aerobic Oxidative Annulation Strategy

et al. 2021

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A catalyst‐free direct aerobic oxidative annulation reaction of 2‐aminobenzylic amines and α‐hydroxy ketones efficiently afforded versatile 5H‐1,4‐benzodiazepine derivatives by employing air as economic and green oxidant under mild conditions. Interestingly, solvent was found to be crucial to the reaction, so that by using acetic acid as the best solvent an efficient and practical method could be achieved, requiring no catalysts or additives at all. This method tolerates a wide range of 2‐aminobenzylic amines and α‐hydroxy ketones and could be scaled up to multigram synthesis and directly applied in one‐step synthesis of the pharmaceutically active N‐desmethylmedazepam derivatives, revealing the potential of this new method in the synthesis of 5H‐1,4‐benzodiazepine skeleton‐based pharmaceuticals and chemicals.

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An expedient approach to substituted triazolo[1,5-a][1,4]benzodiazepines via Cu-catalyzed tandem Ullmann C–N coupling/azide-alkyne cycloaddition

Cited by 39 publications

References 47 publications

An expedient route to highly diversified [1,2,3]triazolo[1,5-a][1,4]benzodiazepines and their evaluation for antimicrobial, antiproliferative and in silico studies

An expedient route to highly diversified [1,2,3]triazolo[1,5-a][1,4]benzodiazepines and their evaluation for antimicrobial, antiproliferative and in silico studies

Tandem synthesis of 1-formyl-1,2,3-triazoles

Efficient Construction of 5H‐1,4‐Benzodiazepine Derivatives by a Catalyst‐Free Direct Aerobic Oxidative Annulation Strategy

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