Effects of Electron-Withdrawing Strengths of the Substituents on the Properties of 4-(Carbazolyl--benzoyl)-5-CF-1-1,2,3-triazole Derivatives as Blue Emitters for Doping-Free Electroluminescence Devices.

The synthesis of four 4-(carbazolyl--benzoyl)-5-CF-1-1,2,3-triazoles with extra groups ((3-methyl)-phenyl-, 4-fluorophenyl-, quinolinyl-, or (3-trifluoromethyl)-phenyl-) in the acceptor fragment has been reported. The effects of substituents with different electron-withdrawing strengths on the thermal, electrochemical, photophysical, and electroluminescence properties of the synthesized compounds are discussed. The results of X-ray analyses and density functional theory (DFT) calculations support unusual molecular packing and electronic properties.

Bioisosteric replacement of 1H-1,2,3-triazole with 1H-tetrazole ring enhances anti-leukemic activity of (5-benzylthiazol-2-yl)benzamides.

Previously, we discovered that N-(5-benzyl-1,3-thiazol-2-yl)-4-(5-methyl-1H-1,2,3-triazol-1-yl)benzamide possessed a remarkable cytotoxic effect on 28 cancer cell lines with IC < 50 μM, including 9 cancer cell lines, where IC was in the range of 2.02-4.70 μM.

Novel N-(4-thiocyanatophenyl)-1H-1,2,3-triazole-4-carboxamides exhibit selective cytotoxic activity at nanomolar doses towards human leukemic T-cells.

The N-(4-thiocyanatophenyl)-1H-1,2,3-triazole-4-carboxamides were synthesized via the condensation of variety of 1H-1,2,3-triazole-4-carboxylic acids and 4-thiocyanatoaniline using CDI as amide coupling reagents. According to computer-aided calculations, all synthesized compounds are expected to have acceptable ADME profile for drug design. The antiproliferative potency of derivatives was evaluated towards different cell lines.

Exciplex-Forming Systems of Physically Mixed and Covalently Bonded Benzoyl-1-1,2,3-Triazole and Carbazole Moieties for Solution-Processed White OLEDs.

Using the newly designed exciplex-forming 1,2,3-triazole-based acceptors with fast and efficient singlet → triplet intersystem crossing (ISC) processes, carbazole and benzoyl-1-1,2,3-triazole derivatives were synthesized by Dimroth-type 1,2,3-triazole ring formation and Ullmann-Goldberg C-N coupling reactions. Due to the exciplex formation between covalently bonded electron-donating (carbazole) and 1,2,3-triazole-based electron-accepting moieties with small singlet-triplet splitting (0.07-0.

Syntheses and crystal structures of two copper(I)-halide π,σ-coordination compounds based on 2-[(prop-2-en-1-yl)sulfan-yl]pyridine.

The title compounds, di-μ-chlorido-bis-({2-[(η-2,3)-(prop-2-en-1-yl)sulfan-yl]pyridine-κ}copper(I)), [CuCl(CHNS)], and di-μ-bromido-bis-({2-[(η-2,3)-(prop-2-en-1-yl)sulfan-yl]pyridine-κ}copper(I)), [CuBr(CHNS)], were obtained by alternating-current electrochemical synthesis starting from an ethano-lic solution of 2-[(prop-2-en-1-yl)sulfan-yl]pyridine () and the copper(II) halide. The isostructural crystals are built up from centrosymmetric [Cu ()] dimers, which are formed due to the π,σ-chelating behavior of the organic ligand. In the crystals, the dimers are linked by C-H⋯ hydrogen bonds as well as by aromatic π-π stacking inter-actions into a three-dimensional network.

Synthesis, crystal structure and Hirshfeld surface analysis of (4-methyl-phen-yl)[1-(penta-fluoro-phen-yl)-5-(tri-fluoro-meth-yl)-1-1,2,3-triazol-4-yl]methanone.

The title compound, CHFNO, was obtained the reaction of 1-azido-2,3,4,5,6-penta-fluoro-benzene with 4,4,4-tri-fluoro-1-(-tol-yl)butane-1,3-dione using tri-ethyl-amine as a base catalyst and solvent. The dihedral angles between the penta-fluoro-phenyl (), triazole () and -tolyl () rings are / = 62.3 (2), / = 43.

Synthesis, crystal structure and Hirshfeld surface analysis of 5-cyclo-propyl--(2-hy-droxy-eth-yl)-1-(4-methyl-phen-yl)-1-1,2,3-triazole-4-carboxamide.

The title compound, CHNO, was obtained a two-step synthesis (Dimroth reaction and amidation) for anti-cancer activity screening and was selected from a 1-1,2,3-triazole-4-carboxamide library. The cyclo-propyl ring is oriented almost perpendicular to the benzene ring [dihedral angle = 87.9 (1)°], while the dihedral angle between the mean plane of the cyclo-propyl ring and that of the triazole ring is 55.

Synthesis, crystal structure and Hirshfeld surface analysis of -(4-chloro-phen-yl)-5-cyclo-propyl-1-(4-meth-oxy-phen-yl)-1-1,2,3-triazole-4-carboxamide.

The title compound, CHClNO, was obtained a two-step synthesis involving the enol-mediated click Dimroth reaction of 4-azido-anisole with methyl 3-cyclo-propyl-3-oxo-propano-ate leading to the 5-cyclo-propyl-1-(4-meth-oxy-phen-yl)-11,2,3-triazole-4-carb-oxy-lic acid and subsequent acid amidation with 4-chloro-aniline by 1,1'-carbonyl-diimidazole (CDI). It crystallizes in space group 2/, with one mol-ecule in the asymmetric unit. In the extended structure, two mol-ecules arranged in a near coplanar fashion relative to the triazole ring planes are inter-connected by N-H⋯N and C-H⋯N hydrogen bonds into a homodimer.

Nitrileimines as an alternative to azides in base-mediated click [3 + 2] cycloaddition with methylene active nitriles.

Nitrileimines were implemented in practical click protocols with oxopropanenitriles for the straightforward 5-amino-1-pyrazole synthesis 1,3-dipolar cycloaddition. The reaction proceeds at room temperature in a short time with base catalysis and no chromatographic purification. High purity products were isolated by simple filtration.

Anticancer Activity Evaluation of New Thieno[2,3-]pyrimidin-4(3)-ones and Thieno[3,2-]pyrimidin-4(3)-one Derivatives.

Anticancer screening of several novel thienopyrimidines has been performed. The thienopyrimidine derivatives were synthesized from available starting materials according to the convenient synthetic procedures using a one-pot solvent-free reaction which gave a wide access to thienopyrimidine-derivative production. The synthesized compounds were preselected via molecular docking to be tested for their anticancer activity in NCI 60 cell lines.

Two Related Copper(I) π-Complexes Based on 2-Allyl-5-(2-pyridyl)-2H-tetrazole Ligand: Synthesis and Structure of [Cu(2-apyt)NO3] and [Cu(2-apyt)(H2O)](BF4) Compounds.

By means of the alternating current electrochemical technique two new π-compounds [Cu(2-apyt)NO3] (1) and [Cu(2-apyt)(H2O)](BF4) (2) have been obtained starting from the mixture of 1-allyl-5-(2-pyridyl)-2H-tetrazole (1-apyt), 2-allyl-5-(2-pyridyl)-2H-tetrazole (2-apyt) and corresponding copper(II) salts, and have been structurally studied. Selective complexation towards 2-allyl- isomer results in a formation of 2-apyt complexes. Copper(I) ion in both 1 and 2 complexes coordinates the allylic C=C bond, one pyridyl and one tetrazole N atoms.

New Convenient Strategy for Annulation of Pyrimidines to Thiophenes or Furans via the One-pot Multistep Cascade Reaction of 1H-Tetrazoles with Aliphatic Amines.

A versatile, convenient, efficient and high-yield synthetic method for 2-R(3),R(4)-amino-5-R(1)-6-R(2)-thieno[2,3-d]pyrimidin-4(3H)-ones, 2-R(3),R(4)-amino-5-R(1)-6-R(2)-thieno[3,2-d]pyrimidin-4(3H)-ones, and benzofuro[3,2-d]pyrimidin-4(3H)-ones preparation has been developed. The reaction proceeded without using solvents and included several steps. A variety of thieno[2,3-d]pyrimidine and thieno[3,2-d]pyrimidine derivatives with substituents of different nature were obtained in high yields from substituted alkyl 2-(1H-tetrazol-1-yl)thiophene-3-carboxylates, 3-(1H-tetrazol-1-yl)thiophene-2-carboxylates, and 3-(1H-tetrazol-1-yl)benzofuran-2-carboxylate after their treatment with aliphatic amines.

Synthesis of 1,2,3-Triazole Derivatives and Evaluation of their Anticancer Activity.

Anticancer screening of several 1,2,3-triazoles with heterocyclic fragments has been performed. The 1,2,3-triazole derivatives were synthesized from available starting materials according to convenient synthetic procedures. The antitumor activity of the synthesized compounds was tested in vitro by the National Cancer Institute in NCI60 cell lines.

First Silver(I) - Complexes with Tetrazole Allyl Derivatives. Synthesis and Crystal Structure of [Ag2(C10H10N4S)2(H2O)2](BF4)2 and [Ag(C10H9ClN4S)(NO3)] π-Compounds (C10H10N4S and C10H9ClN4S - 5-(Allylthio)-1-phenyl- and 5-(Allylthio)-1-(4-chlorophenyl)-1H-tetrazole).

Crystalline silver(I) π complexes [Ag2(atpt)2(H2O)2](BF4)2 (1) (atpt - 5-(allylthio)-1-phenyl-1H-tetrazole (C10H10N4S)) and [Ag(atcpt)(NO3)] (2) (atcpt - 5-(allylthio)-1-(4-chlorophenyl)-1H-tetrazole (C10H9ClN4S)) complexes have been obtained using silver salt and the organic ligands. Compounds were characterized by X-ray single crystal diffraction: for 1 space group P21/n, a = 10.4560(5), b = 11.

One-pot multicomponent synthesis of 1-aryl-5-methyl-N-R2-1H-1,2,3-triazole-4-carboxamides: an easy procedure for combinatorial chemistry.

A convenient synthetic protocol was elaborated for creation of combinatorial libraries of 1-(R(1)-phenyl)-5-methyl-N-R(2)-1H-1,2,3-triazole-4-carboxamides. As starting materials, commercially available or readily prepared azides, amines, and diketene were selected for the reaction which has proceeded in a one-pot system with high yields and in short time.