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Search for "1,2,4-triazole" in Full Text gives 56 result(s) in Beilstein Journal of Organic Chemistry.

Recent advances on organic blue thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs)

  • Thanh-Tuân Bui,
  • Fabrice Goubard,
  • Malika Ibrahim-Ouali,
  • Didier Gigmes and
  • Frédéric Dumur

Beilstein J. Org. Chem. 2018, 14, 282–308, doi:10.3762/bjoc.14.18

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Published 30 Jan 2018

Vinylphosphonium and 2-aminovinylphosphonium salts – preparation and applications in organic synthesis

  • Anna Kuźnik,
  • Roman Mazurkiewicz and
  • Beata Fryczkowska

Beilstein J. Org. Chem. 2017, 13, 2710–2738, doi:10.3762/bjoc.13.269

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  • reaction of 4-amino-5-alkyl-2,4-dihydro-1,2,4-triazole-3-thione with DAAD and triphenylphosphine was reported by Mosslemin et al. [25]. The reaction of triphenylphosphine with DAAD and triazole as the NH-acid and a precursor of the ambident sulfur nucleophile gave the corresponding vinylphosphonium salt 83
  • . Generation of resonance-stabilized phosphorus ylides in the reaction of triphenylphosphine, dialkyl acetylenedicarboxylates, and 1,2,4-triazole-3-thione derivatives. Synthesis of resonance-stabilized phosphorus ylides via the reaction of triphenylphosphine with dialkyl acetylenedicarboxylates and 2
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Published 15 Dec 2017

15N-Labelling and structure determination of adamantylated azolo-azines in solution

  • Sergey L. Deev,
  • Alexander S. Paramonov,
  • Tatyana S. Shestakova,
  • Igor A. Khalymbadzha,
  • Oleg N. Chupakhin,
  • Julia O. Subbotina,
  • Oleg S. Eltsov,
  • Pavel A. Slepukhin,
  • Vladimir L. Rusinov,
  • Alexander S. Arseniev and
  • Zakhar O. Shenkarev

Beilstein J. Org. Chem. 2017, 13, 2535–2548, doi:10.3762/bjoc.13.250

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  • the most efficient way to measure JHN couplings [24]. Previously, the incorporation of a single 15N label in position 1 of the 1,2,4-triazole fragment of compounds 5 and 6 and analysis of the JCN couplings permitted the unambiguous identification of the structures of the N3-adamantylated derivatives
  • by the reisomerization of the initially formed N2-adamantylated product (15a-15N2). Indeed, 2 h of refluxing of isolated 15a-15N2 in TFA with 1.5 molar equivalents of 14 yielded a mixture of compounds 15a-15N2 and 15b-15N2 in the same (1:2) ratio (Scheme 1). The use of [1-15N]-3-amino-1,2,4-triazole
  • -amino-1,2,4-triazole 16-15N2 was synthesized by the interaction of 15N2-hydrazine sulphate (98%, 15N) with S-methyl isothiourea sulphate and consecutive cyclization with formic acid (see the Supporting Information File 1). The use of 16-15N2 in a reaction with ethyl 4,4,4-trifluoroacetoacetate (22
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Published 29 Nov 2017

Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-a]pyrimidine/2-azidopyrimidines

  • Elisandra Scapin,
  • Paulo R. S. Salbego,
  • Caroline R. Bender,
  • Alexandre R. Meyer,
  • Anderson B. Pagliari,
  • Tainára Orlando,
  • Geórgia C. Zimmer,
  • Clarissa P. Frizzo,
  • Helio G. Bonacorso,
  • Nilo Zanatta and
  • Marcos A. P. Martins

Beilstein J. Org. Chem. 2017, 13, 2396–2407, doi:10.3762/bjoc.13.237

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  • atom of the enone, both soft sites of the starting materials [29]. In recent research, we developed an efficient method to obtain 1,2,4-triazolo[1,5-a]pyrimidines from the cyclocondensation reaction of 1,1,1-trifluoro-4-metoxy-3-alken-2-one or β-enaminones with 5-amino-1,2,4-triazole. The methodology
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Published 10 Nov 2017

Synthesis of oligonucleotides on a soluble support

  • Harri Lönnberg

Beilstein J. Org. Chem. 2017, 13, 1368–1387, doi:10.3762/bjoc.13.134

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  • pyridine and 2,6-lutidine using 1-(mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT; 6 equiv) as an activator and N-methylimidazole (NMI; 10 equiv) as a nucleophilic catalyst. Each coupling was followed by precipitation/recrystallization from EtOH, capping with Ac2O in pyridine and precipitation from
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Published 12 Jul 2017

New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

  • Maryna V. Murlykina,
  • Maryna N. Kornet,
  • Sergey M. Desenko,
  • Svetlana V. Shishkina,
  • Oleg V. Shishkin,
  • Aleksander A. Brazhko,
  • Vladimir I. Musatov,
  • Erik V. Van der Eycken and
  • Valentin A. Chebanov

Beilstein J. Org. Chem. 2017, 13, 1050–1063, doi:10.3762/bjoc.13.104

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  • sometimes similar to 3-amino-1,2,4-triazole that was described as a component of GBB-3CR earlier [71][72][73][74][75]. Therefore, the first type of aminoazoles studied in our work was 5-amino-N-aryl-1H-pyrazole-4-carboxamide that showed 1,3-binucleophile properties in the condensation with aromatic
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Published 31 May 2017

Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides

  • Jan Szabo,
  • Julian Greiner and
  • Gerhard Maas

Beilstein J. Org. Chem. 2017, 13, 579–588, doi:10.3762/bjoc.13.57

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  • heating yield 3-hydrazinyl-4-amino-4H-1,2,4-triazole hydrochloride (I, R = H) (Scheme 1) [13]. With the higher homologs of formic acid, the authors of that study observed the formation of resinous materials only. In a recent paper, however, evidence for the formation of the corresponding derivatives of I
  • effectively with 3,4,5-trimethoxybenzoyl chloride (2b) to form the N,N’,N’’-tris(acylamino)guanidinium chloride 3 (Scheme 2). Hydrolysis of the acyl chloride is not a competitive reaction under these conditions, and formation of a 1,2,4-triazole, as observed for the reaction of 1 with formic acid at reflux
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Published 22 Mar 2017

Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles

  • Anastasia S. Kostyuchenko,
  • Tatyana Yu. Zheleznova,
  • Anton J. Stasyuk,
  • Aleksandra Kurowska,
  • Wojciech Domagala,
  • Adam Pron and
  • Alexander S. Fisyuk

Beilstein J. Org. Chem. 2017, 13, 313–322, doi:10.3762/bjoc.13.34

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  • enables the preparation of linear D–A–D compounds with one or two 1,3,4-oxadiazole [16][17][18][19], 1,3,4-thiadiazole [16][18][19][20][21][22] or 1,2,4-triazole [16][18] central rings symmetrically disubstituted with alkylbithiophene 1, 2 as well as star-shaped molecules with D–A arms 3 (Figure 1) [23
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Published 17 Feb 2017

3-Glucosylated 5-amino-1,2,4-oxadiazoles: synthesis and evaluation as glycogen phosphorylase inhibitors

  • Marion Donnier-Maréchal,
  • David Goyard,
  • Vincent Folliard,
  • Tibor Docsa,
  • Pal Gergely,
  • Jean-Pierre Praly and
  • Sébastien Vidal

Beilstein J. Org. Chem. 2015, 11, 499–503, doi:10.3762/bjoc.11.56

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  • around the triazole moiety was also reported [18][19]. The isomeric 1,2,4-triazole E was recently identified as a sub-micromolar GP inhibitor [20][21] and highlights the influence of the aromatic moiety used in these studies. The influence of the heterocyclic moiety was also clearly demonstrated in a
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Published 17 Apr 2015

The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles

  • Marina V. Goryaeva,
  • Yanina V. Burgart,
  • Marina A. Ezhikova,
  • Mikhail I. Kodess and
  • Viktor I. Saloutin

Beilstein J. Org. Chem. 2015, 11, 385–391, doi:10.3762/bjoc.11.44

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  • preparation of compound 11 in the reaction of ester 1f with 5-AT was unexpected, because it is known that ester 1f interacts with 3-amino-1,2,4-triazole in refluxing ethanol [8] and with substituted 5-amino-1,2,4-triazoles in acetic acid [34] to afford triazolo[1,5-a]pyrimidines. However, we did not observe
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Published 23 Mar 2015

The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde

  • Volodymyr V. Tkachenko,
  • Elena A. Muravyova,
  • Sergey M. Desenko,
  • Oleg V. Shishkin,
  • Svetlana V. Shishkina,
  • Dmytro O. Sysoiev,
  • Thomas J. J. Müller and
  • Valentin A. Chebanov

Beilstein J. Org. Chem. 2014, 10, 3019–3030, doi:10.3762/bjoc.10.320

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  • derivatives from salicylaldehyde, various dicarbonyl compounds, and urea (thiourea) using PdO as a catalyst (Scheme 2). Heterocyclizations involving both, salicylaldehyde and aminoazoles, are intriguing as well. Thus, for example in the course of the study on the application of 3-amino-1,2,4-triazole and
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Published 17 Dec 2014

Derivatives of the triaminoguanidinium ion, 3. Multiple N-functionalization of the triaminoguanidinium ion with isocyanates and isothiocyanates

  • Jan Szabo,
  • Kerstin Karger,
  • Nicolas Bucher and
  • Gerhard Maas

Beilstein J. Org. Chem. 2014, 10, 2255–2262, doi:10.3762/bjoc.10.234

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  • triaminoguanidinium salts underwent a threefold carbamoylation with aryl isocyanates to furnish 1,2,3-tris(ureido)guanidinium salts, while p-toluenesulfonyl isocyanate led only to a mono-ureido guanidinium salt. With aryl isothiocyanates, 3-hydrazino-1H-1,2,4-triazole-5(4H)-thione derivatives were obtained. Compounds
  • 7a and 8 show interesting solid-state structures with intra- and intermolecular hydrogen bonds. Keywords: aryl isocyanate; aryl isothiocyanate; carbamoylation; sulfonyl isocyanate; triaminoguanidinium salt; 1H-1,2,4-triazole-5(4H)-thione; Introduction The 1,2,3-triaminoguanidinium ion, [C(NHNH2)3
  • tris(thiourea) derivative, could result. With phenyl isothiocyanate and its 4-nitro derivative, however, 3-hydrazinyl-1H-1,2,4-triazole-5(4H)-thiones 10a,b were obtained as major products in 57 and 68% yield, respectively (Scheme 5). In the case of (4-nitrophenyl) isothiocyanate, the bis(arylthiourea
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Published 24 Sep 2014

Synthesis of new, highly luminescent bis(2,2’-bithiophen-5-yl) substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole

  • Anastasia S. Kostyuchenko,
  • Vyacheslav L.Yurpalov,
  • Aleksandra Kurowska,
  • Wojciech Domagala,
  • Adam Pron and
  • Alexander S. Fisyuk

Beilstein J. Org. Chem. 2014, 10, 1596–1602, doi:10.3762/bjoc.10.165

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  • synthesis, efficient ring closure reaction affording a 4H-1,2,4-triazole unit is presented. All target ambipolar compounds display strong photoluminescence with measured quantum yields up to 0.59. Modification of the demonstrated synthetic routes may be exploited for the preparation of longer, specifically
  • functionalised oligothiophenes, coupled to other heteroaromatic cores. Keywords: bithiophene; donor–acceptor; luminescence; 1,3,4-oxadiazole; 1,3,4-thiadiazole; 4H-1,2,4-triazole; Introduction In the past two decades oligo- and polythiophenes gained a significant research interest due to their wide application
  • -oxadiazole or 1,2,4-triazole central ring are reported herein. The synthesized derivatives are very interesting new semiconductors of possible use as electroluminophores since preliminary studies showed that they could be used as active components of host–guests organic light emitting diodes [21]. Results
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Published 14 Jul 2014

Synthesis of nucleotide–amino acid conjugates designed for photo-CIDNP experiments by a phosphotriester approach

  • Tatyana V. Abramova,
  • Olga B. Morozova,
  • Vladimir N. Silnikov and
  • Alexandra V. Yurkovskaya

Beilstein J. Org. Chem. 2013, 9, 2898–2909, doi:10.3762/bjoc.9.326

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  • ); MALDI–TOFMS (m/z): [M + H]+ calcd for C25H30ClN5O10P, 626.14; found, 626.05; [M + Na]+ calcd for C25H29ClN5NaO10P, 648.12; found, 648.04. General phosphorylation procedure Compound 10, 12, 15, 23, or 26 (0.2 mmol) and 1,2,4-triazole (0.08 g, 1.2 mmol) were coevaporated with Py (3 × 1 mL), dissolved in
  • ) and L-tryptophanol (13). i) N,N’-Dicyclohexylcarbodiimide (DCC), N-hydroxysuccinimide (NHS), 1,4-dioxane, then 2(2-aminoethoxy)ethanol); ii) 2(2-aminoethoxy)ethanol), triethylamine (TEA), 1,4-dioxane; iii) p-chlorophenyl dichlorophosphate, 1,2,4-triazole, pyridine (Py); iv) ethyl trifluoroacetate, TEA
  • , MeIm, Py; ii) AcOH/H2O; iii) p-chlorophenyl dichlorophosphate, 1,2,4-triazole, Py; iv) TBAF in Py/H2O, then HC(O)OH; v) TBAF in Py/H2O, then NH3/H2O. Synthesis of conjugates 6–8. i) TPSCl, MeIm, Py; ii) TBAF in Py/H2O, then NH3/H2O; iii) TBAF in Py/H2O, then NH3/H2O, then AcOH/H2O; iv) Ac2O, Py, then
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Published 18 Dec 2013

One-pot cross-enyne metathesis (CEYM)–Diels–Alder reaction of gem-difluoropropargylic alkynes

  • Santos Fustero,
  • Paula Bello,
  • Javier Miró,
  • María Sánchez-Roselló,
  • Günter Haufe and
  • Carlos del Pozo

Beilstein J. Org. Chem. 2013, 9, 2688–2695, doi:10.3762/bjoc.9.305

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  • generation Hoveyda–Grubbs catalyst I was heated under ethylene atmosphere (1 atm) for 2 h, the clean formation of diene 2a was observed. This newly formed diene was isolated in 70% yield and it reacted smoothly with 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione as dienophile at room temperature to afford, after
  • -difluoro moiety in an efficient manner. However, at this point it is important to mention that when the 1,7-octadiene protocol was applied using maleic anhydride or 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione as dienophiles (Table 1, method B, entries 1, 6 and 9), a complex mixture was obtained. This is
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Published 28 Nov 2013

IBD-mediated oxidative cyclization of pyrimidinylhydrazones and concurrent Dimroth rearrangement: Synthesis of [1,2,4]triazolo[1,5-c]pyrimidine derivatives

  • Caifei Tang,
  • Zhiming Li and
  • Quanrui Wang

Beilstein J. Org. Chem. 2013, 9, 2629–2634, doi:10.3762/bjoc.9.298

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  • isolated products that belong to the [1,5-c] series 6. This kind of rearrangement has been described previously [10][11][21]. The accepted mechanism of the Dimroth rearrangement might involve protonation of 5 to give I (5-H+), ring opening (II), tautomerization by H-shift (III) of the 1,2,4-triazole ring
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Published 25 Nov 2013

[3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions

  • Stephan Cludius-Brandt,
  • Lukas Kupracz and
  • Andreas Kirschning

Beilstein J. Org. Chem. 2013, 9, 1745–1750, doi:10.3762/bjoc.9.201

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  • substituent in vinyl azide 1e provided dihydropyrrole 5e in unsatisfactory yield. The relative stereochemistry of 5i was determined by comparison with literature data [24]. To our delight, this flow protocol also allowed us to prepare 2,3-dihydro-1H-1,2,4-triazole 5j in good yield using diisopropyl
  • dihydropyrroles. The electronic properties of the aromatic ring were of little importance for the principal outcome of the reaction. Notable, azodicarboxylates and electron deficient alkynes were employed for the first time which provided a 1,2,4-triazole and a pyrrole, respectively. Future work should cover a
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Published 26 Aug 2013

Coupling of C-nitro-NH-azoles with arylboronic acids. A route to N-aryl-C-nitroazoles

  • Marta K. Kurpet,
  • Aleksandra Dąbrowska,
  • Małgorzata M. Jarosz,
  • Katarzyna Kajewska-Kania,
  • Nikodem Kuźnik and
  • Jerzy W. Suwiński

Beilstein J. Org. Chem. 2013, 9, 1517–1525, doi:10.3762/bjoc.9.173

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  • been carried out in methanol in the presence of sodium hydroxide to afford the desired N-aryl-C-nitroazoles in good yields. This synthetic route has also been successfully applied to obtain N-phenyl derivatives of 4-nitropyrazole, 2-nitroimidazole, 4(5)-nitroimidazole and 3-nitro-1,2,4-triazole
  • was also investigated. For this purpose the cross coupling of phenylboronic acid with a series of C-nitro-NH-azoles such as: 3(5)-nitropyrazole (1a) (pKa = 9.81) [46], 4-nitropyrazole (1b) (pKa = 9.67) [46], 4(5)-nitroimidazole (1c) (pKa = 8.93) [47], 3-nitro-1,2,4-triazole (1d) (pKa = 6.05) [48] and
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Published 30 Jul 2013

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

  • Paweł Borowiecki,
  • Małgorzata Milner-Krawczyk and
  • Jan Plenkiewicz

Beilstein J. Org. Chem. 2013, 9, 516–525, doi:10.3762/bjoc.9.56

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  • -propylene oxide with imidazole or 1,2,4-triazole. Lipase-catalyzed transesterification of alcohols with vinyl acetate resulted in kinetic enantiomers resolution. Separated (S)-enantiomers of (+)-1-(1H-imidazol-1-yl)propan-2-ol and (+)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol were quaternized with alkyl bromides
  • . Imidazole rings are also frequently present in antibacterial [6][7][8], antifungal [9][10][11][12][13], antiparasitic [14][15], anticancer [16][17] and antiaggregatory [18] preparations. In turn, many 1,2,4-triazole derivatives exhibit antimicrobial [19][20], antifungal [21], antitumor [22], analgesic [23
  • ], anti-inflammatory [24], psychoactive [25][26][27], anticonvulsant [28], diuretic [29], and anti-HIV [30] activity. 1,2,4-Triazole derivatives also represent the most important group of herbicides and fungicides [31]. In recent years growing attention has been focused on imidazole- and 1,2,4-triazole
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Published 12 Mar 2013

Spin state switching in iron coordination compounds

  • Philipp Gütlich,
  • Ana B. Gaspar and
  • Yann Garcia

Beilstein J. Org. Chem. 2013, 9, 342–391, doi:10.3762/bjoc.9.39

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  • isomerism [104]. In addition, structures have been derived from EXAFS spectroscopy, e.g., for iron(II)-1,2,4-triazole polymeric chain compounds [105][106][107][108][109], which, however, is possible in some cases only by comparative studies of analogous Cu compounds. Positron annihilation spectroscopy (PAS
  • ) doped with 1% Mn(II) and later by Haasnoot et al. [120] with [Fe(btr)2(NCS)2]·H2O (btr = 4,4’-bis-1,2,4-triazole) doped with ca. 10% Cu(II). Employing this technique, McGarvey et al. also measured excellent quality EPR spectra of single crystals of [Fe(ptz)6](BF4)2 doped with 1% Mn(II) [121]. They
  • -1,2,4-triazole) [138][139]. Nuclear resonance scattering of synchrotron radiation (NRS) began with the pioneering work of Gerdau et al. in 1985 [71][72][73] who proposed an unconventional Mössbauer spectroscopy technique based on the possibility of using synchrotron radiation for nuclear resonance
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Published 15 Feb 2013

Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds

  • Eugene S. Gladkov,
  • Katerina A. Gura,
  • Svetlana M. Sirko,
  • Sergey M. Desenko,
  • Ulrich Groth and
  • Valentin A. Chebanov

Beilstein J. Org. Chem. 2012, 8, 2100–2105, doi:10.3762/bjoc.8.236

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  • mixture even in trace amounts by TLC, while aminotriazole 1 was isolated unchanged from the reaction mixture. Positional-isomeric compounds 3, whose formation had been expected according to the data published earlier for the similar reactions of 3-amino-1,2,4-triazole [29], was not isolated or even
  • boiling dry ethanol or under MW heating in methanol. The same procedure also allowed us to obtain compounds 5a,b. The best results in this case were observed when the microwave-assisted procedure (Method D) was applied. It should be noted that for similar treatments involving 3-amino-1,2,4-triazole [7][29
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Published 30 Nov 2012

Regioselective synthesis of 7,8-dihydroimidazo[5,1-c][1,2,4]triazine-3,6(2H,4H)-dione derivatives: A new drug-like heterocyclic scaffold

  • Nikolay T. Tzvetkov,
  • Harald Euler and
  • Christa E. Müller

Beilstein J. Org. Chem. 2012, 8, 1584–1593, doi:10.3762/bjoc.8.181

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  • to be introduced. Several synthetic strategies involving combinatorial and sequential approaches, in particular intramolecular cyclocondensation reactions of functionalized 1,2,4-triazole and imidazole precursors, have been developed [5][6][12]. We have been interested in expanding the medicinal
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Published 20 Sep 2012

Chemistry of polyhalogenated nitrobutadienes, 10: Synthesis of highly functionalized heterocycles with a rigid 6-amino-3-azabicyclo[3.1.0]hexane moiety

  • Viktor A. Zapol’skii,
  • Jan C. Namyslo,
  • Armin de Meijere and
  • Dieter E. Kaufmann

Beilstein J. Org. Chem. 2012, 8, 621–628, doi:10.3762/bjoc.8.69

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  • ]hexane 1 in methanol at −40 °C, a twofold vinylic substitution led to the 4,4-bis(aminoazabicyclo[3.1.0]hexyl)-1-chloro-1,3-dinitrobutadiene 13 in 80% yield (Scheme 3). In an analogous treatment of the pentachloronitrobutadiene 3 with a fourfold excess of 1,2,4-triazole in diethyl ether the 4,4
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Published 23 Apr 2012

Advances in synthetic approach to and antifungal activity of triazoles

  • Kumari Shalini,
  • Nitin Kumar,
  • Sushma Drabu and
  • Pramod Kumar Sharma

Beilstein J. Org. Chem. 2011, 7, 668–677, doi:10.3762/bjoc.7.79

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  • membered ring containing two carbon and three nitrogen atoms. Triazoles have two isomeric forms, i.e., 1,2,3-triazole (1) and 1,2,4-triazole (2) (Figure 1). Triazoles are basic aromatic heterocyclic compounds. 1,2,3-Triazoles are surprisingly stable compared to other organic compounds with three adjacent
  • -benzyl]-4-aryl-1,2,4-triazole-3-thiones were synthesized by Ezabadi et al., and evaluated for in vitro antifungal activity against Aspergillus flavus, Aspergillus versicolor, Aspergillus ochraceus, Aspergillus niger, Trichoderma viride and Penicillium funiculosum. Of the compounds obtained, 5-[2-(N,N
  • -diethylsulfamoyl)-4,5-dimethoxybenzyl]-4-(4-chlorophenyl)-1,2,4-triazole-3-thione (6, Figure 4) showed the highest activity [32]. Various 4-amino-2-[4-(4-substituted phenyl)-5-sulfanyl-4H-1,2,4-triazol-3-yl] and 4-amino-2-{4-amino-5-[(4-substituted phenyl)amino]-4H-1,2,4-triazol-3-yl}phenol derivatives were
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Published 25 May 2011

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

  • Marcus Baumann,
  • Ian R. Baxendale,
  • Steven V. Ley and
  • Nikzad Nikbin

Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57

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  • ][77]. 1,2,4-Triazole Although many common antifungal drugs contain at least one 1,2,4-triazole ring, barely any of these drugs are represented in the top 200 drugs based on the value of sales. This observation obviously reflects more the price differential of the drug class rather than the utility of
  • to circumvent the formation of the undesired regioisomer, a strategy that is often used is to react the corresponding benzyl bromide component first with 4-amino-1,2,4-triazole (266) to form a quaternary ammonium salt. The latter can be deaminated to give anastrozole with no isomeric impurities
  • transformation occurs by a two step process: Initially, a molecule of triazine undergoes condensation and ring cleavage with the hydrazine to generate formamidrazone 271 which then immediately reacts with a second molecule of triazine to yield the 1,2,4-triazole [81]. Hence, in this case the triazine can be
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Published 18 Apr 2011
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