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Search for "triazenes" in Full Text gives 6 result(s) in Beilstein Journal of Organic Chemistry.
Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes
- Michio Yamada
Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13
- ][42][43][44][45][46], azulenes and their homologous compounds [32][47][48][49][50][51][52][53][54][55][56][57][58], boron dipyrromethenes (BODIPYs) [41][59][60][61], porphyrins [62][63][64], chlorophylls [65][66], triazenes [67][68], ynamides [69][70][71], arylynamines [72], indoles [73], and γ
Graphical Abstract
Scheme 1: Pathway of the [2 + 2] CA–RE reaction of an electron-rich alkyne with TCNE or TCNQ. EDG = electron-...
Scheme 2: Reaction pathway for DMA-appended acetylene and TCNEO.
Scheme 3: Pathway of the [2 + 2] CA–RE reaction between 1 and DCFs.
Scheme 4: Sequential double [2 + 2] CA–RE reactions between 1 and TCNE.
Scheme 5: Divergent chemical transformation pathways of TCBD 6.
Scheme 6: Synthesis of 12.
Scheme 7: [2 + 2] CA–RE reaction of 1 with 14. TCE = 1,1,2,2-tetrachloroethane.
Scheme 8: Autocatalytic model proposed by Nielsen et al.
Scheme 9: Synthesis of anthracene-embedded TCBD compound 19.
Scheme 10: Sequence of the [2 + 2] CA–RE reaction between dibenzo-fused cyclooctyne or cyclooctadiyne and TCNE...
Scheme 11: [2 + 2] CA–RE reaction between the CPP derivatives and TCNE. THF = tetrahydrofuran.
Scheme 12: [2 + 2] CA–RE reaction between ethynylfullerenes 31 and TCNE and subsequent thermal rearrangement.
Scheme 13: Pathway of the [2 + 2] CA–RE reaction between TCNE and 34, followed by additional skeletal transfor...
Scheme 14: Synthesis scheme for heterocycle 38 from the reaction between TCNE and 1 in water and a surfactant.
Scheme 15: Synthesis scheme of the CDA product 41.
Scheme 16: Synthesis of rotaxanes 44 and 46 via the [2 + 2] CA–RE reaction.
Scheme 17: Synthesis of a CuI bisphenanthroline-based rotaxane 50.
Figure 1: Structures of the chiral push–pull chromophores 51–56.
Figure 2: Structures of the axially chiral TCBD 57 and DCNQ 58 bearing a C60 core.
Figure 3: Structures of the axially chiral SubPc–TCBD–aniline conjugates 59 and 60 and the subporphyrin–TCBD–...
Figure 4: Structures of 63 and the TCBD 64.
Figure 5: Structures of the fluorophore-containing TCBDs 65–67.
Figure 6: Structures of the fluorophore-containing TCBDs 68–72.
Figure 7: Structures of the urea-containing TCBDs 73–75.
Figure 8: Structures of the fullerene–TCBD and DCNQ conjugates 76–79 and their reference compounds 80–83.
Figure 9: Structures of the ZnPc–TCBD–aniline conjugates 84 and 85.
Figure 10: Structures of the ZnP–PCBD and TCBD conjugates 86–88.
Figure 11: Structures of the porphyrin-based donor–acceptor conjugates (89–104).
Figure 12: Structures of the porphyrin–PTZ or DMA conjugates 105–112.
Figure 13: Structures of the BODIPY–Acceptor–TPA or PTZ conjugates 113–116.
Figure 14: Structures of the corrole–TCBD conjugates 117 and 118.
Figure 15: Structure of the dendritic TCBD 119.
Figure 16: Structures of the TCBDs 120–126.
Figure 17: Structures of the precursor 127 and TCBDs 128–130.
Figure 18: Structures of 131–134 utilized for BHJ OSCs.
Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes
- Nicolai Wippert,
- Martin Nieger,
- Claudine Herlan,
- Nicole Jung and
- Stefan Bräse
Beilstein J. Org. Chem. 2021, 17, 2773–2780, doi:10.3762/bjoc.17.187
- ; triazenes; triazines; Introduction The structural motif of pyrazolotriazines, particularly the pyrazolotriazinones, has drawn attention regarding a possible application as therapeutic agents due to manifold biological activities. Amongst other known constitutional isomers such as pyrazolo[4,3-e][1,2,4
- -methylamide-substituted aryltriazenes 7 could be efficiently converted into 3,4-dihydrobenzo[d][1,2,3]triazine derivatives 8 [37] (Scheme 2). In this context, triazenes have shown beneficial properties as they can be used as protected diazonium species which can be handled and converted in various
Graphical Abstract
Scheme 1: Synthesis of 3,6-dihydro-4H-pyrazolo[3,4-d][1,2,3]triazin-4-ones 2a,b by diazotization of 3-amino-1H...
Figure 1: Structural differences of several known (2–4) and so far unknown (5 and 6) pyrazolo[3,4-d][1,2,3]-3H...
Scheme 2: Synthesis of 3,4-dihydrobenzo[d][1,2,3]triazine derivatives 8 from triazene-containing precursors 7 ...
Scheme 3: Planned retrosynthesis to obtain 4,6-dihydropyrazolo[3,4-d][1,2,3]-3H-triazines 5 and 4,7-dihydropy...
Figure 2: Molecular structures of compounds 12h (A) and 13c (B) representing both possible regioisomers of th...
Scheme 4: Cleavage of the triazene protective group and cyclization of the resulting diazonium intermediate y...
Figure 3: Graphical overview about selected pyrazolo[1,2,3]triazines 5 and intermediates 9, 12, and 13 and th...
A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles
- Pezhman Shiri,
- Ali Mohammad Amani and
- Thomas Mayer-Gall
Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114
- . 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
Graphical Abstract
Figure 1: Some significant triazole derivatives [8,23-27].
Scheme 1: A general comparison between synthetic routes for disubstituted 1,2,3-triazole derivatives and full...
Scheme 2: Synthesis of formyltriazoles 3 from the treatment of α-bromoacroleins 1 with azides 2.
Scheme 3: A probable mechanism for the synthesis of formyltriazoles 5 from the treatment of α-bromoacroleins 1...
Scheme 4: Synthesis of 1,4,5-trisubstituted 1,2,3-triazoles 8 from the reaction of aryl azides 7 with enamino...
Scheme 5: Proposed mechanism for the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles from the reaction of a...
Scheme 6: Synthesis of 1,4,5-trisubstituted 1,2,3-triazoles 11 from the reaction of primary amines 10 with 1,...
Scheme 7: The proposed mechanism for the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles 11 from the reacti...
Scheme 8: Synthesis of fully decorated 1,2,3-triazoles 19 containing a sulfur-based side chain.
Scheme 9: Mechanism for the formation of fully decorated 1,2,3-triazoles 19 containing a sulfur-based side ch...
Scheme 10: Synthesis of fully decorated 1,2,3-triazole compounds 25 through the regioselective addition and cy...
Scheme 11: A reasonable mechanism for the synthesis of fully decorated 1,2,3-triazole compounds 25 through the...
Scheme 12: Synthesis of 1,4,5-trisubstituted glycosyl-containing 1,2,3-triazole derivatives 30 from the reacti...
Scheme 13: Synthesis of 1,4,5-trisubstituted 1,2,3-triazoles 34 via intramolecular cyclization reaction of ket...
Scheme 14: Synthesis of fully decorated 1,2,3-triazoles 38 from the reaction of aldehydes 35, amines 36, and α...
Scheme 15: A reasonable mechanism for the synthesis of fully decorated 1,2,3-triazoles 38 from the reaction of...
Scheme 16: Synthesis of functionally rich double C- and N-vinylated 1,2,3-triazoles 45 and 47.
Scheme 17: Synthesis of disubstituted 4-chloro-, 4-bromo-, and 4-iodo-1,2,3-triazoles 50.
Scheme 18: a) A general route for SPAAC in polymer chemistry and b) synthesis of a novel pH-sensitive polymeri...
Scheme 19: Synthesis of 5-allenyl-1,2,3-triazoles 60 by the treatment of alkynes 57, azides 58, and propargyli...
Scheme 20: A reasonable mechanism for the synthesis of 5-allenyl-1,2,3-triazoles 60 by the treatment of alkyne...
Scheme 21: Synthesis of 5‐alkynyl-1,2,3-triazoles 69.
Scheme 22: A reasonable mechanism for the synthesis of 5‐alkynyl-1,2,3-triazoles 69.
Scheme 23: Synthesis of sulfur-cycle-fused 1,2,3-triazoles 75 and 77.
Scheme 24: A reasonable mechanism for the synthesis of sulfur-cycle-fused 1,2,3‐triazoles 75 and 77.
Scheme 25: Synthesis of 5-selanyltriazoles 85 from the reaction of ethynylstibanes 82, organic azides 83, and ...
Scheme 26: A mechanism for the synthesis of 5-selanyltriazoles 85 from the reaction of ethynylstibanes 82, org...
Scheme 27: Synthesis of trisubstituted triazoles containing an Sb substituent at position C5 in 93 and 5-unsub...
Scheme 28: Synthesis of asymmetric triazole disulfides 98 from disulfide-containing tert-butyltosyl disulfide 97...
Scheme 29: A mechanism for the synthesis of asymmetric triazole disulfides 98 from disulfide-containing tert-bu...
Scheme 30: Synthesis of triazole-fused sultams 104.
Scheme 31: Synthesis of 1,2,3-triazole-fused tricyclic heterocycles 106.
Scheme 32: A reasonable mechanism for the synthesis of 1,2,3-triazole-fused tricyclic heterocycles 106.
Scheme 33: Synthesis of 5-aryl-substituted 1,2,3-triazole derivatives 112.
Scheme 34: A reasonable mechanism for the synthesis of 5-aryl-substituted 1,2,3-triazole derivatives 112.
Scheme 35: Synthesis of 1,4,5-trisubstituted 1,2,3-triazole-5-carboxamides 119.
Scheme 36: A probable mechanism for the synthesis of 1,4,5-trisubstituted 1,2,3-triazole-5-carboxamides 119.
Scheme 37: Synthesis of fully decorated triazoles 125 via the Pd/C-catalyzed arylation of disubstituted triazo...
Scheme 38: Synthesis of triazolo[1,5-a]indolones 131.
Scheme 39: Synthesis of unsymmetrically substituted triazole-fused enediyne systems 135 and 5-aryl-4-ethynyltr...
Scheme 40: Synthesis of Pd/Cu-BNP 139 and application of 139 in the synthesis of polycyclic triazoles 142.
Scheme 41: A probable mechanism for the synthesis of polycyclic triazoles 142.
Scheme 42: Synthesis of highly functionalized 1,2,3-triazole-fused 5-, 6-, and 7-membered rings 152–154.
Scheme 43: A probable mechanism for the synthesis of highly functionalized 1,2,3-triazole-fused 5-, 6-, and 7-...
Scheme 44: Synthesis of fully functionalized 1,2,3-triazolo-fused chromenes 162, 164, and 166 via the intramol...
Scheme 45: Ru-catalyzed synthesis of fully decorated triazoles 172.
Scheme 46: Synthesis of 4-cyano-1,2,3-triazoles 175.
Scheme 47: Synthesis of functionalized triazoles from the reaction of 1-alkyltriazenes 176 and azides 177 and ...
Scheme 48: Mechanism for the synthesis of functionalized triazoles from the reaction of 1-alkyltriazenes 176 a...
An overview of recent advances in duplex DNA recognition by small molecules
- Sayantan Bhaduri,
- Nihar Ranjan and
- Dev P. Arya
Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93
Graphical Abstract
Figure 1: A figure showing the hydrogen bonding patterns observed in (a) duplex (b) triplex and (c) quadruple...
Figure 2: (a) Portions of MATα1–MATα2 are shown contacting the minor groove of the DNA substrate. Key arginin...
Figure 3: Chemical structures of naturally occurring and synthetic hybrid minor groove binders.
Figure 4: Synthetic structural analogs of distamycin A by replacing one or more pyrrole rings with other hete...
Figure 5: Pictorial representation of the binding model of pyrrole–imidazole (Py/Im) polyamides based on the ...
Figure 6: Chemical structures of synthetic “hairpin” pyrrole–imidazole (Py/Im) conjugates.
Figure 7: (a) Minor groove complex formation between DNA duplex and 8-ring cyclic Py/Im polyamide (conjugate ...
Figure 8: Telomere-targeting tandem hairpin Py/Im polyamides 23 and 24 capable of recognizing >10 base pairs; ...
Figure 9: Representative examples of recently developed DNA minor groove binders.
Figure 10: Chemical structures of bisbenzamidazoles Hoechst 33258 and 33342 and their synthetic structural ana...
Figure 11: Chemical structures of bisamidines such as diminazene, DAPI, pentamidine and their synthetic struct...
Figure 12: Representative examples of recently developed bisamidine derivatives.
Figure 13: Chemical structures of chromomycin, mithramycin and their synthetic structural analogs 91 and 92.
Figure 14: Chemical structures of well-known naturally occurring DNA binding intercalators.
Figure 15: Naturally occurring indolocarbazole rebeccamycin and its synthetic analogs.
Figure 16: Representative examples of naturally occurring and synthetic derivatives of DNA intercalating agent...
Figure 17: Several recent synthetic varieties of DNA intercalators.
Figure 18: Aminoglycoside (neomycin)–Hoechst 33258/intercalator conjugates.
Figure 19: Chemical structures of triazole linked neomycin dimers and neomycin–bisbenzimidazole conjugates.
Figure 20: Representative examples of naturally occurring and synthetic analogs of DNA binding alkylating agen...
Figure 21: Chemical structures of naturally occurring and synthetic analogs of pyrrolobenzodiazepines.
Synthesis and chemosensing properties of cinnoline-containing poly(arylene ethynylene)s
- Natalia A. Danilkina,
- Petr S. Vlasov,
- Semen M. Vodianik,
- Andrey A. Kruchinin,
- Yuri G. Vlasov and
- Irina A. Balova
Beilstein J. Org. Chem. 2015, 11, 373–384, doi:10.3762/bjoc.11.43
- -dibromocinnolines 4a,b (Table 1). Triazenes 3a,b were synthesized from 4-bromo-2-iodophenyltriazene 1 by the Sonogashira coupling [44][45] with hexyne (2a) and TMS-protected diacetylene 2b using conditions for the one-pot TMS group removal and the Sonogashira coupling developed recently [46]. The last reaction
- synthetic steps. 4,6-Dibromo-3-butylcinnoline (4a) and 4,6-dibromo-3-(hept-1-yn-1-yl)cinnoline (4b) were obtained from corresponding triazenes 3a,b by Richter cyclization under known conditions [43] in satisfactory and good yields. Although the Sonogashira coupling of 4-bromocinnolines has been recently
Graphical Abstract
Figure 1: Recent examples of PAEs and their application for the detection of Hg2+ (a) [11], Ni2+ (b) [12], explosives...
Figure 2: Target structures of PAEs.
Scheme 1: Synthesis of cinnoline-containing PAEs 10a,b.
Figure 3: 1H NMR spectra of PAEs 10a,b solutions in CDCl3.
Figure 4: 13C NMR spectra of PAEs 10a,b solutions in CDCl3.
Figure 5: Irregular chain structure (nonequivalent structural units are marked in different colors).
Figure 6: Optical absorption spectra of PAEs 10a,b in THF solutions.
Figure 7: Emission spectra of PAEs 10a,b in THF solutions.
Figure 8: Optical absorption spectra of PAE 10a in THF before and after the addition of metal analytes.
Figure 9: Optical absorption spectra of PAE 10b in THF before and after the addition of metal analytes.
Figure 10: Emission spectra of PAE 10a in THF before and after the addition of metal ions.
Figure 11: Emission spectra of PAE 10b in THF before and after the addition of metal ions.
Figure 12: Optical absorption spectra of PAE 10a in THF before and after the addition of HCl (10 equiv).
Figure 13: Emission spectra of PAE 10a in THF before and after the addition of HCl (10 equiv).
Figure 14: Optical absorption spectra of PAE 10b in THF before after the addition of methanol solution of PdCl2...
Figure 15: Emission spectra of PAE 10b in THF before and after the addition of methanol solution of PdCl2.
Figure 16: Optical absorption spectra of cinnoline 4a in THF before and after the addition of aqueous solution...
Figure 17: Emission spectra of cinnoline 4a in THF before and after the addition of aqueous solution of PdCl2.
Suzuki–Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene–palladium complex catalyst
- Guangming Nan,
- Fang Ren and
- Meiming Luo
Beilstein J. Org. Chem. 2010, 6, No. 70, doi:10.3762/bjoc.6.70
- 5, entries 5, 6). Notably, good reactivity and chemoselectivity were achieved with 1-(4-bromophenyl)- and 1-(4-iodophenyl)-2-(pyrrolidin-1-yl)diazene (Table 5, entries 5, 6), showing that triazenes were more active than the corresponding aryl bromides and iodides under these reaction conditions
Graphical Abstract
Scheme 1: Synthesis of the polymer-supported NHC–Pd catalyst 1.
Scheme 2: Reaction of 1-(3-nitrophenyl)-2-(pyrrolidin-1-yl)diazene and phenylboronic acid.
