Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate, a reagent that is used for the synthesis of the analogs of netropsin and distamycin, exists as a molecule that is disordered in the carboxyethyl substituent. The disorder is the consequence of packing (Wu et al., 2004). Hydrolysis of this ester yields the title carboxylicacid, which crystallizes as a dihydrate, (I) (Fig. 1). The acid molecule is planar; the molecules interact with the water molecules to form a three-dimensional hydrogen-bonded network (Fig. 2 and Table 2).
It is well known that many triazole-related molecules have received much attention due to their biological activities (Olesen et al., 2003; Tian et al., 2005). We report herein the crystal structure of the title compound, (I, Fig. 1). The bond lengths and angles have normal values. The dihedral angle between the triazole and phenyl planes is 84.80 (2)°. The packing of the molecules is stabilized by strong hydrogen bonds (Table 1) between the triazole molecules and lattice water molecules. Meanwhile, the 0D discrete molecules are arranged into a three-dimensional framework via hydrogen bond interactions and weak contacts (Fig. 2).
A solution of phenylphosphorodichloridate (7a)( 0.002 mole) in 25 ml of dry toluene was added drop wise over a period of 20 minutes to a stirred solution of 1-(benzo [d] oxazol-2-yl ) methyl) -1H- imidazole-4,5-diyl) dimethanol (6a) (0.002mole) and triethylamine (0.004mole) in 30 ml of dry toluene and 10ml of tetrahydrofuran at 5 0 C . After completion of the addition, the temperature of the reaction mixture was slowly raised to room temperature and stirred for 2 hours. Later the reaction mixture was heated to 50-60 O C and maintained for 4 hours with stirring. The completion of the reaction was monitored by TLC analysis. After completion of the reaction the Triethyl amine hydrochloric acid was filtered from mixture and solvent was removed under reduced pressure. The residue was washed with water and then recrystalized from aqueous 2-propanol to get pure compound  of 1(benzo [d] oxazol-2-yl - methyl) - 6- phenoxy-4,8-dihydro-1H-[1,3,2] dioxaphosphepino [5,6-d] imidazole-6-oxide (6a)
The title compound was synthesized by refluxing a mixture of 2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetohydrazide (0.1 mol) and 1-(4-methoxyphenyl)ethanone (0.1 mol) in glacial acetic acid for 1 h. On cooling the reaction mixture to room temperature and evaporation of the solvent under reduced pressure, the solid that separated out was filtered, washed with water and dried. Yellow plate-shaped crystals were grown from ethanol-dioxane mixture by slow evaporation method (m.p. 505 K).
group lies in the plane of the imidazole group. In the crystal structure (Fig. 2), intermolecular N—H O hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers. The packing is further stabilized by weak C—H O and C— H N interactions (Table 2).
The structure consists of two 1-(2-hydroxyethyl)2-methyl-5-nitroimidazole ligands coordinating to the silver through the N atoms in a distorted linear configuration, indicated by the N3—Ag1—N1 angle of 165.34 (4) °. The bond lengths of Ag1—N3 = 2.147 (11) Å and Ag1—N1 = 2.148 (11) Å, are comparable to the values reported for similar silver coordinated complexes (Tong & Chen, 2000; Ni et al., 2003; You & Zhu, 2004; Gao et al., 2004). The bond lengths of the heterocyclic five membered rings are comparable with the values found in 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole in its un-coordinated form (Blaton et al., 1979), iodometronidazole (Yang et al., 2005), and chlorometronidazole (Pi et al., 2005).
dihydrate, was obtained by Cu I -catalysed azide–alkyne cyclo- addition from 2-azido-1-methylimidazole and phenylethyne. The dihedral angles between the central triazole ring (r.m.s. deviation = 0.004 A ˚ ) and the pendant imidazole (r.m.s. deviation = 0.006 A ˚ ) and phenyl rings are 12.3 (2) and 2.54 (19) , respectively. In the crystal, the water molecules
A suspension of 1-H-pyrazole-4, 5-dimethanol (1Mmole) (1) was dissolved in acetone (5ml) and 2, 2-dimethoxy propane (DMP, 2Mmole) solvent mixture. To the reaction mixture phosphotungstic acid (PTA, 5mole %) was added. The reaction mixture was stirred at room temperature for 4 hours under argon atmosphere until the 1-H- pyrazole-4; 5-dimethanol (1) had dissolved. The progress of the reaction was monitored by TLC using cyclohexane and ethyl acetate (9:1) solvent mixture as an eluent. After completion of the reaction, it was observed that the catalyst forms a gummy mass to stick on the wall inside the reaction flask. The solvent was decanted, dried under reduced pressure and the dried mass was re dissolved in dichloromethane (DCM). The dichloromethane solution was washed with water, dried with Na 2 SO 4 and evaporated to get the crude product (2), which was recrystallized by
, (II), were obtained from solutions containing 2-methylimidazole and nitric acid in different concentrations. In the crystal structure of salt (I), one of the –NH H atoms of the imidazole ring shows half-occupancy, hence only every second molecule is in its cationic form. The nitrate anion in this structure lies on a twofold rotation axis. The neutral 2-methylimidazole molecule and the 2-methyl-1H-imidazol-3-ium cation interact through N—H N hydrogen bonds to form [(C 4 H 6 N 2 ) (C 4 H 7 N 2 )
The title compound contains two independent molecules in an asymmetric unit (Fig. 1) with identical conformations. The two imidazole rings (C2—C4/N2/N3 and C9—C11/N5/N7) are individually planar with r.m.s.d's 0.0038 and 0.0019 Å, respectively; the dihedral angle between the mean planes of the imidazole rings is 9.25 (19)°. The nitro groups N1/O1/O2 and N4/O6/O7 are oriented at 4.5 (2) and 6.44 (13)° with respect to the imidazole rings (C2—C4/N2/N3) and (C9—C11/N5/N7), respectively. The bond distances and angles in both molecules of the title compound agree very well with the corresponding bond distances and angles reported in closely related compounds (Yousuf et al., 2012; Zeb et al., 2012). The crystal packing (Fig. 2) is consolidated by weak intermolecular C—H···O and C—H···N type hydrogen bonds (Table 1).
Condensation of 4-(4-methoxybenzylidene)-2-methyl-1H-imidazol-5(4H)-one (IV) with 4-nitro- o-phenylene-1,2-diamine and p-toluene sulphonic acid in 1:1:1 molar proportion in ethanol at room temperature for 24 hours and second reaction is condensation of IV with 4-nitro-o- phenylene-1,2-diamine (II) and p-toluene sulphonic acid in 1:1:1 molar proportion in ethanol and reflux on hot water bath for one hour, orange coloured compound is separated for both procedures which are recrystallised from ethanol. The compounds were found to be same as evidenced from T.L.C and spectral studies.
methanol solvent molecule, which is, in turn, linked to the cation by an O— H O hydrogen bond; the components of the structure are linked by O—H O hydrogen bonds, forming chains along . One of the MET ligands and the BF 4 anion are disordered over two sets of sites with ratios of refined
melatonin. Other indolic compounds include the plant hormone Auxin. Naturally occurring hallucinogen dimethyl tryptamine. Indole possess a wide variety of pharmacological properties such as analgesic1-4, antiinflammatory5-8, antimicrobial9-13, anticancer14-15, anticonvulsant16 and anti-HBV17 activities. Substituted indoles like indomethacin (1) exhibits analgesic activity by inhibition of cyclooxygenase enzyme (COX) which catalyze the bioconversion of arachidonic acid to inflammatory mediators i.e prostaglandins (PGs) and thromboxanes (TXs).18 We synthesized T1-T5 indole derivatives as indomethacin analogues in which i) -CH2COOH group at position -3 is replaced with proline, ii) -OCH3 group at position -5 is replaced with -Br and iii) Chlorbenzoyl group at position -1 is replaced with various halides.
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
ecules in the asymmetric unit. Each molecule forms stacks with its own kind, the stacks being approximately orthogonal to each other. Both Br atoms in molecule 1 form Lewis acid± base interactions with N atoms in molecule 2, with Br N distances of 3.078 (4) and 3.264 (4) AÊ.
A mixture of 2-methyl-4-nitro-1-imidazo thiosemicarbazide (1 mmol) and conc. sulfuric acid (1 ml) was heated under reflux for 2–3 h. The resulting solution was cooled, poured into crushed ice and treated with sodium carbonate to pH 6. The precipitate was collected by filtration and washed with water. The solid formed was filtered and recrystallized from ethanol-DMF mixture to yield red blocks (Melting point 251 °C).
Periodic acid (2.8 mmol, 0.64 g), pyridinium chlorochromate (PCC, 4 mol%) were suspended in acetonitrile (20 ml) and stirred vigorously for five minutes. The mixture was allowed to cool on an ice-salt bath followed by the addition of secnidazole (2.7 mmol, 0.50 g) and allowed to stir for 36 h at ambient temperature. After the completion of the reaction [TLC analysis], the reaction mixture was washed with brine/water (1:1 v/v), saturated aqueous Na 2 SO 3 solution, dried
For the synthesis of Phenyl-1, 2-di (3H-benzo [d] imidazole-5-carboxylicacid the mixture of phthalodinitrile (0.50 g), o-phenyline-4-benzoicacid (11.40 g) and sulfur (0.06 g) was irradiated for 25 minutes by the general method as described above. Yield: 81%, mp. 210 0 C, PMR (DMSOd 6 ): 8.5 (d, 1H, ArH), 8.1(d, 1H, ArH), 7.9 (d, 1H, ArH), 7.5 (d, 3H, ArH), 7.2