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Synthesis of 1,3,4-oxadiazoles - Organic Chemistry Portal

Categories: Synthesis of N-Heterocycles, Synthesis of O-Heterocycles > Synthesis of 1,3,4-oxadiazoles

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PDF Downloads : Oriental Journal of Chemistry

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Sigma-Aldrich Online Catalog Product List: C4 to C7

All melting points were determined on a Melt-Temp R apparatus equipped with a digital thermometer and are uncorrected. The IR spectra were measured as potassium bromide pellets on a Digilab Scimitar Series FT-IR Spectrophotometer; the wave numbers are given in cm-1. The 1H-NMR spectra were recorded in DMSO-d6 or CD3COCD3 solutions on Bruker ARX-300 spectrometer at ambient temperature. Chemical shifts were recorded as δ values in parts per millions (ppm) and were indirectly referenced to tetramethylsilane via residual solvent signal (2.49 for 1H). MS spectra were obtained using an instrument produced by Agilent Technologies, Wilmington, DE, USA. The instrument, Accurate Mass Q-TOF LC/MS 6520 was operated via the manufacture’s software, Mass Hunter. Samples were dissolved in acetonitrile/water mixture (95/5 v/v) to obtain a concentration of 10 μg/mL and 0.05 mL were directly injected into the electrospray source using the auto sampler at a rate of 0.05 ml/min. The instrument was operated in High resolution mode with an acquisition rate of 4 GHz. The source voltage was set at 4,000 V, the spray gas flow at 5 L/min, heating gas temperature at 325 °C and the fragmentor potential at 215 V. All chemical reagents were obtained from the Aldrich Chemical Company.

The chemistry of isatins: a review from 1975 to 1999 - …

N’’-phenylthiocarbonohydrazide: phenylhydrazine (0.1 mol) was dissolve in ethanol (95%, 50ml) and ammonia solution 20 ml then CS2 (20 ml) was added slowly within 15 min with shaking and solution allow to stand for 1 hr. to it sodium chloroacetate (0.10 mol) and 50% hydrazine hydrate (20 ml)was added. The reaction mixture was warmed gently, filtered and evaporated to half of its volume and kept overnight. The solid thus obtained was filtered and purified by recrystallization from ethanol.

2-(substituted phenyl)-5-(2-phenylhydrazinyl)-1,3,4-thiadiazole: a mixture of N’’-phenylthiocarbonohydrazide (0.10 mol), an aromatic acid and phosphorous oxychloride (25 ml) was refluxed for 18-22 hr. after cooling to RT the reaction mixture was poured into the crushed ice and kept overnight. The solid thus separated was filtered, washed with water, dried and purified by recrystallization from methanol.

The Chemistry of Isatins: a Review from 1975 to 1999

All rights reserved.A new series of thiosemicarbazones (TSCs) and their 1,3,4-thiadiazolines(TDZs) containing acetamide group have been synthesized fromthiosemicarbazide compounds by the reaction of TSCs with cyclic ketonesas well as aromatic aldehydes.

Products of Compounds containing a 1-1,2,4- triazole derivatives and many mono-, di- and tri-substituted 1,2,4-triazole-5-thiones Polyamide containing -methylimidazole (Im) can be combined in antiparallel side-by-side dimericcomplexes with the minor groove of DNA[11], also compound 2-Amino-3-(4-carboxy-1-imidazol-1-yl) propionic acid has been examined as an inhibitor of diaminopimelic acid dehydrogenase from [12]

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  • Synthesis of Related Compounds of Thiosemicarbazide. …


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Synthesis of Related Compounds of Thiosemicarbazide

Novel derivatives of 1,2,4,-triazole, 1,3,4-thiadiazole and 1,3,4-oxadiazole were synthesized from cyclization of new 1-[4-(phenylsulfonyl)benzoyl]-4-(4-fluorophenyl)-thiosemicarbazide 2 which was obtained by reaction of the 4-(phenylsulfonyl)-benzoic acid hydrazide 1 with 4-fluorophenyl isothiocyanate. The compound 2, in basic medium, gave 1,2,4-triazole-3(4H)-thione 3, whereas in acidic medium 1,3,4-thiadiazol-2-amine 5 was obtained. The synthesis of 1,3,4-oxadiazol-2-amine 6 was carried out by reaction of the same acylthiosemicarbazide 2 with yellow mercuric oxide. Treatment of 1,2,4-triazole 3 with ethyl bromoacetate led to the S-alkylated 1,2,4-triazole derivative 4. The newly synthesized compounds were characterized by elemental analysis and spectral studies (IR, UV-VIS, 1H-NMR, 13C-NMR, MS). All the synthesized compounds have been evaluated in vitro for their antibacterial activity against several strains of pneumococci and different type/reference strains of oral streptococci.

Preparation of halomethyl-1,3,4-thiadiazoles

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