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Search for "triazene" in Full Text gives 7 result(s) in Beilstein Journal of Organic Chemistry.
Synthesis of substituted triazole–pyrazole hybrids using triazenylpyrazole precursors
Beilstein J. Org. Chem. 2024, 20, 1396–1404, doi:10.3762/bjoc.20.121
- addition, the compatibility of the method with solid-phase synthesis is shown exemplarily. Keywords: azide; click reaction; CuAAC; pyrazole; triazene; triazole; Introduction Nitrogen-containing heterocycles are central scaffolds in medicinal chemistry and are incorporated in most small-molecule drugs [1
- sources and thus as building blocks for synthesizing pyrazolyltriazoles by CuAAC reactions. To find a feasible approach to pyrazolyltriazoles of type 1 with a highly substituted scaffold, we decided to explore the benefits of a modification of the triazene-protected pyrazole core. In the next step, a
- benzylic residues differed depending on the benzylic residue's functional groups and the pyrazole substitution pattern. For starting materials 15a and 15d, an excess of product 17 was usually observed. With the ester-functionalized triazene 15c and m-substituted benzylic reagents, regioisomer 18 was the
Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes
Beilstein J. Org. Chem. 2021, 17, 2773–2780, doi:10.3762/bjoc.17.187
- 4,6-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines, were not successful under similar conditions due to the higher stability of the triazene functionality in the regioisomeric precursors and thus, the failure of the removal of the protective group. Keywords: cyclization; diazonium chemistry; pyrazoles
- have a major influence on the outcome of the reaction: (1) the addition of side chains R1 to the core pyrazole ring system, which can occur in position N-6 or N-7, and (2) the cyclative cleavage of the triazene group of compounds 9 and 10 which should lead to the target compounds 5 and 6. To carry out
- shown with compound 12g (R1 = -CH2CO2Et), being reduced to compound 17g (R1' = -(CH2)2OH) and acylated to 9i with R1'' = -(CH2)2OCOMe. The last step in the synthesis of the target compounds 5a–i included the cleavage of the triazene unit of the amides 9 with subsequent cyclization to the final pyrazolo
A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles
Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114
- of the imine intermediate produces the intermediate enamine 13. The 1,3-dipolar cycloaddition of enamine 13 with azide produces intermediate 1,2,3-triazoline 14. In continuation, a ring-opening process is promoted by acetic acid to afford the intermediate 16. Afterward, triazene intermediate 17 was
- were formed through a Ru-catalyzed azide–alkyne cycloaddition process. The current protocol tolerates a range of aromatic and aliphatic azides, affording a diverse range of 4-cyano-1,2,3-triazoles 175 (Scheme 46) [67]. Ir-catalyzed synthesis of fully decorated triazoles A series of triazene
- . Moreover, TMS-substituted alkyne was suitable for this Huisgen reaction to achieve the desired triazole product. Next, some triazene scaffolds, such as dimethylamino-, pyrrolidine-, piperidine-, morpholine-, and piperazine-derived triazenes were screened. Aryl azides containing Br, I, Me, and MeO as well
Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes
Beilstein J. Org. Chem. 2015, 11, 1494–1502, doi:10.3762/bjoc.11.162
- established that the hydrogen atom in the product comes exclusively from THF and not from pyridine or MeCN (Table 4). The observed deuterium enrichment using THF-d8 was around 80%. Thermal decomposition of aryldiazonium salts prepared from immobilized triazene precursors and the formation of deuterated
Macrocyclic bis(ureas) as ligands for anion complexation
Beilstein J. Org. Chem. 2014, 10, 1834–1839, doi:10.3762/bjoc.10.193
- bis(triazene), in which two diphenyltriazene units were linked by two ethynylene groups. On deprotonation, a dianionic planar bis(triazenide) ligand is formed, which takes up several different transition metal ions, preferredly in the divalent state [10]. Linking two diphenylurea groups by one
- of log K = 2.55 for the complexation of Cl− was determined [11]. Introducing a second bridging unit would give a ring containing two diphenylurea units connected via two stiff linking units. Since the urea unit N−C(O)−N and the triazenide unit N−N=N are isosteric, we complemented our bis(triazene
Photochemistry with laser radiation in condensed phase using miniaturized photoreactors
Beilstein J. Org. Chem. 2012, 8, 1213–1218, doi:10.3762/bjoc.8.135
- , and several side-products, such as the corresponding azo-derivatives, are usually formed [36][40][41][42][43][44]. During the past few years, we successfully employed triazene resins, such as 4, which are readily available from aniline in the synthesis of a library of aromatic derivatives [45][46][47
- ][48]. Moreover, triazene-resins are perfectly suitable for the synthesis of arylazides 5 (Scheme 2) [49]. The photochemical decomposition of arylazides into carbazoles is appropriate for application in miniaturized photoreactors, since significant results can be observed by an online analysis through
Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents
Beilstein J. Org. Chem. 2011, 7, 1261–1277, doi:10.3762/bjoc.7.147
- iPrMgCl·LiCl also proves to be very practical for the generation of polyfunctional alkenylmagnesium reagents, which react only slowly with iPrMgCl [40][41], as well as for the preparation of arylmagnesium reagents bearing sensitive functionalities, such as triazene. Thus, aryl iodide 79 is treated with
- iPrMgCl·LiCl (64) at −40 °C for 1 h leading to an intermediate magnesium reagent, which after transmetalation to the corresponding zinc reagent using ZnBr2 provides, after Negishi cross-coupling reaction with the bromoquinoline 80, the polyfunctinal triazene 81 in 75% yield. The conversion of the triazene
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