Showing papers on "Triazene published in 2011"

Modification of activated carbons based on diazonium ionsin situ produced from aminobenzene organic acid without addition of other acid

Abstract: Activated carbon products modified with a benzene sulfonic acid group were prepared based on the spontaneous reduction of diazonium salts in situ generated in water without addition of an external acid. The diazotization reaction assisted by the organic acid substituent, produced at once amine, diazonium and triazene functionalities that maximize the grafting yield by a chemical cooperation effect.

Synthesis and characterization of triazenes derived from sulfonamides

Abstract: A series of novel triazene derivatives 1-3, 1a-3a were synthesized by the cou- pling of diazonium salts of amines (sulfaguanidine, sulfapyridine, sulfamethoxazole) with N-methylaniline / p-nitroaniline in acidic media. The structures of the synthesized com- pounds were confirmed by the spectral data (UV, IR, 1H-NMR, APCI-MS) and elemental anal- ysis. The effects of all the compounds on A 549 and L 929 cell lines growth were investigat- ed. The cytotoxic and antitumor activities of these compounds have not been in vitro aganist A 549 and L 929 cell lines.

Synthesis and reactivity with M(II) (M=Co and Cu) chloride of 1-[(2-carboxyethyl)benzene]-3-[benzothiazole]triazene

Abstract: Reaction of ethyl anthranilate, sodium nitrite, and 2-aminobenzothiazole produces a new triazenide compound, 1-[(2-carboxyethyl)benzene]-3-[benzothiazole]triazene (HL), which has been characterized by X-ray crystallography and NMR spectrum. In the presence of Et3N, reaction of HL and CuCl2 · 2H2O or CoCl2 · 6H2O in THF/methanol affords a tetranuclear copper(II) complex [Cu4L4(µ-OMe)4] · 4THF (1) and a cobalt(III) complex [CoL′3] (2) (L′ is 1-[benzothiazole] triazene ion), accompanied by C–N bond cleavage of HL. They are characterized by X-ray crystallography and magnetic susceptibility measurement. Magnetic studies indicate significant antiferromagnetic coupling between the copper(II) centers for 1. The value obtained for the coupling constant J is −585 cm−1.

Solvatochromism and potentiometic studies of some active nitroso- and nitroso-azo- compounds

Abstract: The stability studies of biologically active 2,4-dinitrosoresorcinol, o-carboxy phenylazo-dinitrosoresorcinol, N , N `-bis-[4,4`-(1,3-diphenyltriazine)]-diacetamide, 2-amino-6-phenylazo-pyridin-3-ol, 2-amino-3-hydroxy-pyridin-6-ylazo)-benzoic acid, 4-(2-amino-3-hydroxy-pyridin-6-ylazo)-benzoic acid ethyl ester and N -[4-(2-amino-3-hydroxy-pyridin-6-ylazo)-phenyl]-acetamide compounds were studied. The dissociation constants were determined potentiometrically. The thermodynamic parameters of dissociation were evaluated. Regression analysis is applied for correlating the different parameters. The results help to assign the solute-solvent interactions and the solvatochromic potential of the investigated compounds. The electronic character of the substituent and the chemical nature of the solvent are major factors for the observed solvatochromism.

Copper complexes of 1-[(2-carboxyethyl)benzene]-3-[2-pyridine]triazene

Abstract: The triazenide, 1-[(2-carboxyethyl)benzene]-3-[2-pyridine]triazene (HL), has been synthesized. In the presence of Et3N, the reaction of HL with Cu(OAc)2·H2O or CuCl2·2H2O gives the tetranuclear copper(II) complexes {Cu4(L)2(μ2-OH)2(OAc)4} 1 and {Cu4L4(μ4-O)Cl2} 2, respectively. The X-ray crystal structures of both complexes have been obtained. Magnetic studies indicate significant antiferromagnetic coupling between the copper(II) centers for both complexes, with coupling constants (J) of −493.4 cm−1 for 1 and −165 cm−1 for 2.

3-(2-Eth-oxy-phen-yl)-1-(3-nitro-phen-yl)triaz-1-ene.

Abstract: The title compound, C14H14N4O3, exhibits a trans geometry about the N=N double bond in the triazene unit. The mol­ecule is approximately planar (r.m.s. deviation = 0.044 A for all non-H atoms). An intra­molecular N—H⋯O hydrogen bond occurs. In the crystal, C—H⋯N hydrogen bonds lead to the formation of dimers which are, in turn, connected to each other by C—H⋯O hydrogen bonds, forming infinite chains of R 2 2(8) graph-set motif.

Synthesis of quinolines involving electrophilic amination of arenes with sodium azide in polyphosphoric acid

Abstract: Quinolines are well known compounds for which a considerable number of synthetic methods have been developed.1 Nevertheless, no methods including the for mation of the N(1)—C(8a) and С(4)—C(4a) bonds were known in the literature. In the present work, we proposed such a method, which is based on the recently found re agent combination NaN3/polyphosphoric acid (PPA*). 3 We showed that the reactions of phenol (1a) and anisole (1b) with NaN3 in PPA at 55—60 °C for 3 h followed by addition of 1,3 dicarbonyl compound 2a,b and heating for additional 3 h at 120—130 °C afford quinolines 3a—с in yields of 31—42% (Scheme 1). The proposed mechanism of this transformation in cludes the formation of triazene 4 according to the mech anism analogous to that given in Ref. 3, the electrophilic attack of 4 by 1,3 dicarbonyl compound, cyclization of intermediate 5 to compound 6, and decomposition of the latter to yield azomethine 7, whose intramolecular alkyla tion affords quinolines 3 (Scheme 2). Thus, the consecutive reaction of sodium azide and a 1,3 dicarbonyl compound with an aromatic compound in PPA results in quinolines through the one pot reaction. In future, we intend to study to what extent this reaction is general with respect to aromatic and heteroaromatic com pounds.

Azidomethyl Phenyl Sulfide

Abstract: [77422-70-9] C7H7N3S (MW 165.22) InChI = 1/C7H7N3S/c8-10-9-6-11-7-4-2-1-3-5-7/h1-5H,6H2 InChIKey = KIQGRMGPIMCXSC-UHFFFAOYAE (reagent for amination of organomagnesium compounds;1 allows amination and oxidation of α,α-disubstituted ester enolates via 1,2,3-triazol-5-ones;1b a synthetic equivalent of methyl azide for the synthesis of methylaziridines;2 substituted α-azido sulfides undergo Beckmann-type rearrangements to provide lactams and imino thioethers3, 4) Physical Data:bp 104–105 °C/5 mmHg; n20D 1.5904; d 1.168 g mL−1; fp 107 °C. Solubility: freely sol common organic solvents. Form Supplied in: colorless to light-gold liquid, ∼95% pure. Analysis of Reagent Purity: 1H NMR. Preparative Method: chlorination of Thioanisole with Sulfuryl Chloride followed by treatment of the resultant α-chloro sulfide with Sodium Azide in acetonitrile.1a Handling, Storage, and Precautions: as with all azides of low or moderate molecular weight, heat or shock can cause vigorous, possibly explosive, nitrogen evolution. Distillation should be performed behind a blast shield at reduced pressure and temperatures less than 110 °C. Similar compounds have been shown to decompose with nitrogen evolution at ∼120 °C.5 Striking neat azidomethyl phenyl sulfide with a hammer fails to cause detonation. Storage under nitrogen in an amber bottle in a refrigerator is recommended. It is incompatible with strong acids, bases, and oxidizing agents. When the reagent is used for the amination of organomagnesium reagents, an intermediate triazene is formed. Certain triazenes are known to be carcinogenic,6 thus caution in handling these intermediates should be exercised. Rinsing glassware with bleach will dispel the disagreeable odor associated with azidomethyl phenyl sulfide, phenylthiomethyltriazenes, and other sulfur-containing byproducts encountered in the use of this reagent. Handle in a fumehood.