Debenzylation of Functionalized 4- and 5-Substituted 1,2,3-Triazoles

Farooq, Tahir; Sydnes, Leiv K.; Törnroos, Karl W.; Haug, Bengt Erik

doi:10.1055/s-0031-1291160

Cited by 14 publications

(2 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Alternative methods to prepare compounds 5b, 70 5i, [70][71][72] 5o, 37 and 5y 30 were reported in the literature. Since we already described the synthesis of 5a 30 and 5k 28 , these procedures are not repeated here.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of N-unsubstituted 1,2,3-triazoles via a cascade including propargyl azides, allenyl azides, and triazafulvenes

Banert¹,

Hagedorn²,

Hemeltjen³

et al. 2016

Arkivoc

View full text Add to dashboard Cite

About thirty NH-1,2,3-triazoles with at least one additional functional group in a side chain at C-4 were prepared from propargyl substrates. These reactions included propargyl azides and their [3,3]-sigmatropic rearrangement to generate short-lived allenyl azides, which cyclized to form triazafulvenes that could be trapped by addition of N-or O-nucleophiles. In most cases, simple substrates and cheap sodium azide were utilized as starting compounds, and the syntheses were performed by using a one-pot procedure without isolation of any dangerous azides. This method to prepare NH-1,2,3-triazoles turned out to be compatible with quite different substitution patterns of the propargyl substrate.

show abstract

Section: Methodsmentioning

confidence: 99%

Synthesis of N-unsubstituted 1,2,3-triazoles via a cascade including propargyl azides, allenyl azides, and triazafulvenes

Banert¹,

Hagedorn²,

Hemeltjen³

et al. 2016

Arkivoc

View full text Add to dashboard Cite

show abstract

“…Furthermore, imine derivatives have been synthesized as interesting ligands in coordination chemistry [19][20][21]. 1-Substituted 4-formyl-1,2,3-triazoles are commonly prepared via a two-step synthesis involving the copper-catalyzed azide-alkyne cycloaddition reaction with azides and propargyl alcohol [2,[9][10][11][12][13][15][16][17][18]22] or acetal-protected propargyl aldehydes [3,5,6,8,23,24], followed by oxidation or hydrolysis, respectively. These methods are clever alternatives for the cycloaddition between azides and the low boiling propynal, which is inconvenient to handle.…”

Section: Introductionmentioning

confidence: 99%

1-(4-Nitrophenyl)-1H-1,2,3-Triazole-4-carbaldehyde: Scalable Synthesis and Its Use in the Preparation of 1-Alkyl-4-Formyl-1,2,3-triazoles

et al. 2021

View full text Add to dashboard Cite

1,2,3-Triazole-4-carbaldehydes are useful synthetic intermediates which may play an important role in the discovery of novel applications of the 1,2,3-triazole moiety. In this work, a one-step multigram scale synthesis of 4-formyl-1-(4-nitrophenyl)-1H-1,2,3-triazole (FNPT) as a preferred reagent for the synthesis of 1-alkyl-4-formyltriazoles is described, making use of the commercially available 3-dimethylaminoacrolein and 4-nitrophenyl azide. Next, the earlier reported reaction of FNPT with alkylamines is further explored, and for hexylamine, the one-pot sequential cycloaddition and Cornforth rearrangement is demonstrated. In addition, a useful protocol for the in situ diazotization of 4-nitroaniline is provided. This facilitated the complete hydrolysis of rearranged 4-iminomethyl-1,2,3-triazoles and allowed for the recycling of 4-nitrophenyl azide.

show abstract

Hierarchical Silica Inverse Opals as a Catalyst Support for Asymmetric Molecular Heterogeneous Catalysis with Chiral Rh‐diene Complexes

et al. 2021

View full text Add to dashboard Cite

The efficacy of heterogeneous catalysis relies heavily on diffusion and distribution of reactants within catalyst supports. However, the presence of confinement, essential for reaction selectivity, drastically slows down molecular transport. Here, macro-mesoporous silica inverse opal (SiO 2 À IO) films were used as a model system to study the rather unexplored molecular infiltration behavior using a probe molecule resembling a catalyst via confocal laser scanning microscopy (CLSM). CLSM analysis revealed homogeneous tracer distribution in SiO 2 À IO and attachment to both transport and mesopores. Bulk macro-mesoporous SiO 2 À IO support was used for the attachment of mono-and bis-functionalized chiral Rh-diene complexes, and the catalytic activity and selectivity with respect to the support was studied. Lower enantioselectivity was observed with the bis-functionalized ligand due to ligand entanglement and reduced accessibility of the active site, while the monofunctionalized ligand gave an excellent enantioselectivity of 94 %ee in the asymmetric 1,2-addition of triphenylboroxine to N-tosylimines and could be recycled up to three times.

show abstract

Debenzylation of Functionalized 4- and 5-Substituted 1,2,3-Triazoles

Cited by 14 publications

References 20 publications

Synthesis of N-unsubstituted 1,2,3-triazoles via a cascade including propargyl azides, allenyl azides, and triazafulvenes

Synthesis of N-unsubstituted 1,2,3-triazoles via a cascade including propargyl azides, allenyl azides, and triazafulvenes

1-(4-Nitrophenyl)-1H-1,2,3-Triazole-4-carbaldehyde: Scalable Synthesis and Its Use in the Preparation of 1-Alkyl-4-Formyl-1,2,3-triazoles

Hierarchical Silica Inverse Opals as a Catalyst Support for Asymmetric Molecular Heterogeneous Catalysis with Chiral Rh‐diene Complexes

Contact Info

Product

Resources

About