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Search for "4H-1,2,4-triazole" in Full Text gives 5 result(s) in Beilstein Journal of Organic Chemistry.
Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins
- Chandra Sekhar Tekuri,
- Pargat Singh and
- Mahendra Nath
Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89
- -tetraarylporphyrins 1 were synthesized from the corresponding 2-nitro-meso-tetraarylporphyrins in two steps by following the literature procedure [42]. The first step involved an amination of copper(II) 2-nitro-meso-tetraarylporphyrins by using 4-amino-4H-1,2,4-triazole in the presence of NaOH in refluxing ethanol
Graphical Abstract
Scheme 1: Synthesis of benzo[f]chromeno[2,3-h]quinoxalinoporphyrins 3–16.
Figure 1: Plausible mechanism for the formation of copper(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrins.
Scheme 2: Sequential synthesis of copper(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrin 3.
Figure 2: Electronic absorption spectra of copper(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrins 3–8 in CHCl...
Figure 3: Electronic absorption spectra of free-base benzo[f]chromeno[2,3-h]quinoxalinoporphyrins 9–13 in CHCl...
Figure 4: Electronic absorption spectra of zinc(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrins 14–16 in CHCl...
Figure 5: (a) Emission spectra of free-base benzo[f]chromeno[2,3-h]quinoxalinoporphyrins 9–13 and (b) emissio...
Double-headed nucleosides: Synthesis and applications
- Vineet Verma,
- Jyotirmoy Maity,
- Vipin K. Maikhuri,
- Ritika Sharma,
- Himal K. Ganguly and
- Ashok K. Prasad
Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98
- ], 6,7-dihydro-6-oxo-5H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine [17], 1,2,4-triazino[5,6-b]indole [18], 1,3,4-thiadiazoline [19], 1,3,4-oxadiazoline [19], 1,2,4-triazoline [19], 3-mercapto-1H-1,2,4-triazole [20], 1,3,4-oxadiazole-2(3H)-thione [20], 4-amino-5-mercapto-4H-1,2,4-triazole [20], and 1,2,4
Graphical Abstract
Figure 1: Double-headed nucleosides. B1 and B2 = nucleobases or heterocyclic/carbocyclic moieties; L = linker....
Scheme 1: Synthesis of 2′-(pyrimidin-1-yl)methyl- or 2′-(purin-9-yl)methyl-substituted double-headed nucleosi...
Scheme 2: Synthesis of double-headed nucleoside 7 having two cytosine moieties.
Scheme 3: Synthesis of double-headed nucleoside 2′-deoxy-2′-C-(2-(thymine-1-yl)ethyl)-uridine (11).
Scheme 4: Double-headed nucleosides 14 and 15 obtained by click reaction.
Scheme 5: Synthesis of the double-headed nucleoside 19.
Scheme 6: Synthesis of the double-headed nucleosides 24 and 25.
Scheme 7: Synthesis of double-headed nucleosides 28 and 29.
Scheme 8: Synthesis of double-headed nucleoside 33.
Scheme 9: Synthesis of double-headed nucleoside 37.
Scheme 10: Synthesis of the double-headed nucleoside 1-(5′-O-(4,4′-dimethoxytrityl)-2′-C-((4-(pyren-1-yl)-1,2,...
Scheme 11: Synthesis of triazole-containing double-headed ribonucleosides 46a–c and 50a–e.
Scheme 12: Synthesis of double-headed nucleosides 54a–g.
Scheme 13: Synthesis of double-headed nucleosides 59 and 60.
Scheme 14: Synthesis of the double-headed nucleosides 63 and 64.
Scheme 15: Synthesis of double-headed nucleosides 66a–c.
Scheme 16: Synthesis of benzoxazole-containing double-headed nucleosides 69 and 71 from 5′-amino-5′-deoxynucle...
Scheme 17: Synthesis of 4′-C-((N6-benzoyladenin-9-yl)methyl)thymidine (75) and 4′-C-((thymin-1-yl)methyl)thymi...
Scheme 18: Synthesis of double-headed nucleosides 5′-(adenine-9-yl)-5′-deoxythymidine (79) and 5′-(adenine-9-y...
Scheme 19: Synthesis of double-headed nucleosides 85–87 via reversed nucleosides methodology.
Scheme 20: Double-headed nucleosides 91 and 92 derived from ω-terminal-acetylenic sugar derivatives 90a,b.
Scheme 21: Synthesis of double-headed nucleosides 96a–g.
Scheme 22: Synthesis of double-headed nucleosides 100 and 103.
Scheme 23: Double-headed nucleosides 104 and 105 with a triazole motif.
Scheme 24: Synthesis of the double-headed nucleosides 107 and 108.
Scheme 25: Synthesis of double-headed nucleoside 110 with additional nucleobase in 5′-(S)-C-position joined th...
Scheme 26: Synthesis of double-headed nucleosides 111–113 with additional nucleobases in the 5′-(S)-C-position...
Scheme 27: Synthesis of double-headed nucleoside 114 by click reaction.
Scheme 28: Synthesis of double-headed nucleosides 118 with an additional nucleobase at the 5′-(S)-C-position.
Scheme 29: Synthesis of bicyclic double-headed nucleoside 122.
Scheme 30: Synthesis of double-headed nucleosides 125a–c derived from 2′-amino-LNA.
Scheme 31: Double-headed nucleoside 127 obtained by click reaction.
Scheme 32: Synthesis of double-headed nucleoside 130.
Scheme 33: Double-headed nucleosides 132a–d and 134a–d synthesized by Sonogashira cross coupling reaction.
Scheme 34: Synthesis of double-headed nucleosides 137 and 138 via Suzuki coupling.
Scheme 35: Synthesis of double-headed nucleosides 140 and 141 via Sonogashira cross coupling reaction.
Scheme 36: Synthesis of double-headed nucleoside 143.
Scheme 37: Synthesis of the double-headed nucleoside 146.
Scheme 38: Synthesis of 5-C-alkynyl-functionalized double-headed nucleosides 151a–d.
Scheme 39: Synthesis of 5-C-triazolyl-functionalized double-headed nucleosides 154a, b.
Scheme 40: Synthesis of double-headed nucleosides 157a–c.
Scheme 41: Synthesis of double-headed nucleoside 159, phosphoramidite 160 and the corresponding nucleotide mon...
Scheme 42: Synthesis of double-headed nucleoside 163, phosphoramidite 164 and the corresponding nucleotide mon...
Scheme 43: Synthesis of double-headed nucleoside 167, phosphoramidite 168, and the corresponding nucleotide mo...
Scheme 44: Synthesis of double-headed nucleoside 171, phosphoramidite 172, and the corresponding nucleotide mo...
Scheme 45: Synthesis of double-headed nucleoside 175, phosphoramidite 176, and the corresponding nucleotide mo...
Scheme 46: Synthesis of double-headed nucleoside 178.
Scheme 47: Synthesis of the double-headed nucleosides 181 and 183.
Scheme 48: Alternative synthesis of the double-headed nucleoside 183.
Scheme 49: Synthesis of double-headed nucleoside 188 through thermal [2 + 3] sydnone–alkyne cycloaddition reac...
Scheme 50: Synthesis of the double-headed nucleosides 190 and 191.
Scheme 51: Synthesis of 1-((5S)-2,3,4-tri-O-acetyl-5-(2,6-dichloropurin-9-yl)-β-ᴅ-xylopyranosyl)uracil (195).
Scheme 52: Synthesis of hexopyranosyl double-headed pyrimidine homonucleosides 200a–c.
Figure 2: 3′-C-Ethynyl-β-ᴅ-allopyranonucleoside derivatives 201a–f.
Scheme 53: Synthesis of 3′-C-(1,4-disubstituted-1,2,3-triazolyl)-double-headed pyranonucleosides 203–207.
Scheme 54: Synthesis of 3′-C-(1,4-disubstituted-1,2,3-triazolyl)-double-headed pyranonucleosides 208 and 209.
Scheme 55: Synthesis of 3′-C-(1,4-disubstituted-1,2,3-triazolyl)-double-headed pyranonucleoside 210.
Scheme 56: Synthesis of double-headed acyclic nucleosides (2S,3R)-1,4-bis(thymine-1-yl)butane-2,3-diol (213a) ...
Scheme 57: Synthesis of double-headed acyclic nucleosides (2R,3S)-1,4-bis(thymine-1-yl)butane-2,3-diol (213c) ...
Scheme 58: Synthesis of double-headed acetylated 1,3,4-oxadiazino[6,5-b]indolium-substituted C-nucleosides 218b...
Scheme 59: Synthesis of double-headed acyclic nucleoside 222.
Scheme 60: Synthesis of functionalized 1,2-bis(1,2,4-triazol-3-yl)ethane-1,2-diols 223a–f.
Scheme 61: Synthesis of acyclic double-headed 1,2,4-triazino[5,6-b]indole C-nucleosides 226–231.
Scheme 62: Synthesis of double-headed 1,3,4-thiadiazoline, 1,3,4-oxadiazoline, and 1,2,4-triazoline acyclo C-n...
Scheme 63: Synthesis of double-headed acyclo C-nucleosides 240–242.
Scheme 64: Synthesis of double-headed acyclo C-nucleoside 246.
Scheme 65: Synthesis of acyclo double-headed nucleoside 250.
Scheme 66: Synthesis of acyclo double-headed nucleoside 253.
Scheme 67: Synthesis of acyclo double-headed nucleosides 259a–d.
Scheme 68: Synthesis of acyclo double-headed nucleoside 261.
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
Graphical Abstract
Figure 1: Radiative deactivation pathways existing in fluorescent, phosphorescent and TADF materials.
Figure 2: Boron-containing TADF emitters B1–B10.
Figure 3: Diphenylsulfone-based TADF emitters D1–D7.
Figure 4: Triazine-based TADF emitters T1–T3, T5–T7 and azasiline derivatives T3 and T4.
Figure 5: Triazine-based TADF emitters T8, T9, T11–T14 and carbazole derivative T10.
Figure 6: Triazine-based TADF emitters T15–T19.
Figure 7: Triazine- and pyrimidine-based TADF emitters T20–T26.
Figure 8: Pyrimidine-based TADF emitters T27–T30.
Figure 9: Triazine-based TADF polymers T31–T32.
Figure 10: Phenoxaphosphine oxide and phenoxathiin dioxide-based TADF emitters P1 and P2.
Figure 11: CN-Substituted pyridine and pyrimidine derivatives CN-P1–CN-P8.
Figure 12: CN-Substituted pyridine derivatives CN-P9 and CN-P10.
Figure 13: Phosphine oxide-based TADF blue emitters PO-1–PO-3.
Figure 14: Phosphine oxide-based TADF blue emitters PO-4–PO-9.
Figure 15: Benzonitrile-based emitters BN-1–BN-5.
Figure 16: Benzonitrile-based emitters BN-6–BN-11.
Figure 17: Benzoylpyridine-carbazole hybrid emitters BP-1–BP-6.
Figure 18: Benzoylpyridine-carbazole hybrid emitters BP-7–BP-10.
Figure 19: Triazole-based emitters Trz-1 and Trz-2.
Figure 20: Triarylamine-based emitters TPA-1–TPA-3.
Figure 21: Distribution of the CIE coordinates of ca. 90 blue TADF emitters listed in this review.
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
- 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
Graphical Abstract
Scheme 1: Reactions of aminoguanidines with carboxylic acids and acid chlorides. The structural formulae show...
Scheme 2: Threefold N-acylation of triaminoguanidinium chloride (1) with acyl chloride 2b.
Scheme 3: Reaction of 1,2,3-tris(benzylamino)guanidinium salts 4 and 5 with acyl chlorides to give 1,2,3-tris...
Figure 1: Molecular structure of 6b·2C2H5OH in the solid state, with numbering of atoms (ORTEP plot). Selecte...
Scheme 4: Protonation and methylation of 1,2,4-triazolium-3-aminides 7b,c.
Scheme 5: Catalytic hydrogenation/debenzylation of betaines 7.
Figure 2: Left: molecular structure of 8b in the solid state (OLEX2 plot). Right: crystal structure viewed al...
Figure 3: Left: solid-state structure of 9b·H2O (ORTEP plot). Right: centrosymmetric hydrogen-bonded dimer of...
Figure 4: Solid-state structure of mesoionic compound 7a (ORTEP plot); thermal displacement ellipsoids are dr...
Figure 5: UV–vis spectra of 7a–d in chloroform (c = 0.04 mmol L−1); λmax [nm] (ε [L mol−1 cm−1]): 7a: 350 (47...
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
- 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
- with phosphorus oxychloride, in 78 and 83% yields, respectively. The reaction of 11 with a Lawesson’s reagent led to the formation of 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-tiadiazole (15, 70% yield) (Scheme 4). To the contrary, 3,5-bis(3-decyl-2,2'-bithiophen-5-yl)-4-phenyl-4H-1,2,4-triazole (18
Graphical Abstract
Scheme 1: Synthesis of ethyl 3-decyl-2,2'-bithiophene-5-carboxylate (3).
Scheme 2: Synthesis of ethyl 4-(hexyloxy)-2,2'-bithiophene-5-carboxylate (7).
Scheme 3: Hydrolysis and hydrazinolysis of esters 8–10.
Scheme 4: Synthesis of 2,5-bis(2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles 13 and 14 and 1,3,4-thiadiazole 15.
Scheme 5: Synthesis of 3,5-bis(3-decyl-2,2'-bithiophen-5-yl)-4-phenyl-4H-1,2,4-triazole (18).
Figure 1: UV–vis absorption and fluorescence spectra of diluted solutions of a) 13, b) 14, c) 15, and d) 18 i...
Figure 2: Photoluminescence quantum yields measured for 13, 15 and 18 together with their formulae.
