To the solution of methanol (50 ml) and KOH (1.1eq), carbon disulphide (1.1eq) was added slowly at room temperature. To the reaction mass, 2-aminophenol (1.eq) was added with stirring. The reaction mass was refluxed for 6 hr on water bath. Completion of the reaction was monitored by TLC. The reaction mixture was poured to a beaker containing ice cold water and acidified with glacial acetic acid (pH 6). The obtained solid was filtered, dried and recrystallized using ethanol to get the compound 1,3-benzoxazole-2-thiol 1. The different derivatives of 1,3-benzoxazole-2-thiol were synthesized by similar method by using various 2-amino phenols. Colour: white; IR (KBr, cm-1): 3386 cm-1 (-SH); 1H NMR (DMSO-d6, δ ppm): 7.3(s, H Ar-H),6.9(dd, H Ar-H), …show more content…
The cold reaction mixture was stirred for 10 min and slowly POCl3 was added drop by drop to the cold solution. The reaction temperature was maintained to 00C and refluxed for 5 hr. The completion of reaction was checked by TLC. The reaction mass was poured onto crushed ice to get solid product. The obtained solid was filtered, dried and recrystallize using ethyl acetate to get compound 2-chloroquinoline-3-carbaldehyde …show more content…
(iii) Synthesis of 13H benz[4’,5’]oxazole[2’,3’,:2,3][1,3]thiazino[6,5-b]quinolin-13-one 4 The compound 124 (0.01mol) was treated with 2-chloroquinoline-3-carbaldehyde 2 (0.01mol) in presence of DMF used as a solvent and refluxed for 8 hr. Then the reaction mixture was poured onto crushed ice. The solid product thus obtained was filtered, dried and recrystallized from ethanol to get compound 4. The compounds 5-15 have been prepared by following same procedure. Colour: white; IR (KBr, cm-1): 1670 cm-1 (C=O); 1H NMR (DMSO-d6, δ ppm): 8.24(m, 2H Ar-H), 8.07(d, 2H Ar-H), 8.33(s, H Ar-H), 7.52(d, 2H Ar-H), 7.78(m, 2H Ar-H), 6.52(s, H -H); 13CNMR (DMSO-d6, δ ppm): 112-155(17C, Ar-C); 172(1C, C=O); M+,306. (iv) Synthesis of 10-chloro-6aH,13Hbenz[4’,5’]oxazole[2’,3’,:2,3][1,3]thiazino[6,5b]quinolin-13-one 5 Colour: cream; IR (KBr, cm-1): 1672 cm-1 (C=O); 1H NMR (DMSO-d6, δ ppm): 8.37(s, H Ar-H), 8.02(dd, H Ar-H), 8.25(dd, H Ar-H), 7.88(s, H Ar-H), 7.68(d, 2H Ar-H), 7.29(m, 2H Ar-H), 6.59(s, H -H); 13C NMR (DMSO-d6, δ ppm): 115-158(17C, Ar-C), 178(1C, C=O); M+,340,
Chloroacetic acid (0.5 g, 5. 28 mmol), 5-aminotetrazole monohydrate (0.45 g, 5. 28 mmol), and sodium hydroxide (0.59 g, 10.57 mmol) in 10 ml of water was refluxed 20 hr, cooled, and made strongly acidic with concentrated hydrochloric acid. The mixture was cooled overnight and precipitate was separated to give 0.28 g a white solid product at 45.41% yield. (5-Amino-tetrazol-1-yl)-acetic acid: Yield: 45.41%; white crystals; m.p 210-213°C; IR (KBr): 3388, 3315, 3270, 3205, 3010, 2976, 1697, 1638, 1586, 1496, 1257 cm-1; 13C NMR (75 MHz (DMSO-d6)): 168, 156,
purified through preparative LC as described above and finally characterized as phloretin and phloridzin (Fig. 1). Compound 1 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one or phlorizin was obtained as amorphous powder, mp 2620C. The UV/Visible spectrum of the compound showed λmax at 225 and 285 nm. ESI–MS m/z 297 [M+Na]+ in positive ion mode and 273 [M-H] in negative ion mode for molecular formula C15H14O5; 274.
As early as 1930 simple derivatives such as 33 were patented as agents for the protection of wool against moths.52 Later, interest focused on the antiviral activity of Biginelli compounds,53 eventually leading to the development of nitractin (34), which has excellent activity against the viruses of the trachoma group.14,54 The Biginelli compounds also exhibits modest antibacterial activity. 55 Dihydropyrimidinone 1 and some of its analogs were screened as antitumor agents and found to be active against Walker carcinosarcoma in rats and mice.55-57 Pyrimidine 5-carboxamides of type 35 are reported to possess anticarcinogenic58 activity. Antinflammatory,9,59 antioxidant,59b analgesic,9 and blood platelet aggregation inhibitory activity 8 was found in a number of derivatives.
The solution was stirred at room temperature for 8h. The solvent was blown out with nitrogen. The residue was added to 1 ml of water containing 0.1% TFA and purified on RP-HPLC. Massspec of the final product clearly indicates presence of RB modified on PEI by series of peaks matching different polymer compositions (see Fig. 6). RP-HPLC program: 0-5 min 5-30 min 30-35 min 20% MeCN 20-85% MeCN 85-99% MeCN 5-{3-(3-N-polyethyleniminemaleimide)propylamidophenyl}-10,15,20-tris(4-sulfonato-phenyl)porphyrin trisodium salt (TPPS-PEI) (8b) TPPS-Mal (20 mM) in 500 μL of dry DMF was titrated to 500 μL of 40 mM polyethylenimine in dry DMF.
2.1 Material N,N-Dimethyl formamide (DMF), 2,2-Azobisisobutyronitrile (AIBN), Silver nitrate (AgNO3) and Methanol were purchased from the lobachemie Pvt. Ltd. (India). Styrene monomer was procured from the sigma-Aldrich. Co. The solvents DMF and methanol were distilled for purification.
J.T. Desaiet al. [4] reported the ecofriendly synthesis of isoxazoline moiety containing bridge at 2 º amine and also
Kaur,1985) which give sigmoid shape with (n-hexane, n-heptane and n-decane), i.e. show both negative and positive values at low and high mole fraction range. This can be explained as consequence of two opposing effects, the disruption of H-bonded alcohol aggregates by alkane molecules contribute negative VE whereas change in free volume and interstitial accommodation of smaller alkane molecules into the alkanol structure give negative contribution. The latter effect gets stoically hindered in 4-methylpentan-2-ol due to positive contribution due and is dominated by the positive contribute due to disruption of H-bonds. Self association due to H-bonds also become weaker due to steric hindrance to H-bond formation in 4-methylpentan-2-ol as compared to Hexan-1-ol which cause more positive VE values for 4-methylpentan-2-ol. The shape of the molecule is another factor which contributes more positive value of VE to 4-methylpentan-2-ol.
1,3,4-Oxadiazole (1) is a heterocyclic compound containing an oxygen atom and two nitrogen atoms in a five-membered ring. It is derived from furan by substitution of two methylene groups (=CH) with two pyridine type nitrogens (-N=) [1,2]. There are three known isomers: 1,2,4-oxadiazole (2), 1,2,3-oxadiazole (3) and 1,2,5-oxadiazole (4). However, 1,3,4-oxadiazole and 1,2,4-oxadiazole are better known, and more widely studied by researchers because of their many important chemical and biological properties.
The reaction mixture was then cooled and poured into crushed ice with constant stirring and left overnight. A dark red coloured copolymer was obtained and washed with warm water, methanol and acetone followed by filtration to remove unreacted monomers and impurities. Finally, the copolymer was dried in an air oven at 75 °C for 24 h. The yield of the copolymer was found to be 85%. The copolymer was found to be soluble in solvents like dimethylsulphoxide, dimethylformamide and tetrahydrofuran and partially soluble in mineral acids.
2.3. Synthesis of 2-(2-(Morpholinomethyl)-1H-benzimidazol-1-yl)acetohydrazide (4) To a solution of compound 3 (0.01 M, 2.89 g) in methanol (60 mL), 99% hydrazine hydrate (1 mL) was added and the mixture was refluxed for 6 h. The reaction mixture was cooled and the solid thus obtained was filtered, washed with cold water and recrystallized with ethanol to obtain the compound 4. 2.4.
Synthesis of 2-[(4-methoxy-phenyl)iminomethyl]-4-nitrophenol (SB) The Schiff-base, 2-[(4-methoxy-phenyl)iminomethyl]-4-nitrophenol, (C14H12N2O4) was synthesized by using p-Anisidine in methanol
An easy synthesis of 5-trifluoromethylated oxazole compounds as a building block which would be able to transform into effectively useful pharmaceuticals or chemicals can be achieved to improve the practical use. In this study, we describe the new synthesis of methyl 5-trifluoromethyl-2-phenyloxazole-4-carboxylate which derived from 4-alkoxy oxazole in one-pot by utilizing Cornforth rearrangement. At this time, we took an interest in the experimental result that no precursors of rearrangement were detected in this reaction. The strategy of designing and synthesizing compounds that inhibited reclosure from nitrile ylide resulted in successful capture of unstable precursors.
Scope of the Oxa-Pictet-Spengler reaction for the synthesis of oxazinoindoles ENTRY R1 R2 R3 PRODUCT YIELD DIASTERIOMER RATIO 1 H H Ph 69l 85 >19:1 2 H H CH2OBn 69a 60 >19:1 3 H ----------(CH2)4-----------
S. DRUG SUBSTANCE S1. General Information S1.1 Nomenclature Table 84 Nomenclature of Drug Substance International Nonproprietary Name (INN) Levofloxacin Hemihydrate Chemical Name 7H-Pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-hydrate (2:1), (S)-.(-)-(S)-9-Fluoro-2,3-dihydro-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7Hpyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, hemihydrates Generic name Levofloxacin Hemihydrate CAS Number [138199-71-0] S1.2 Structure and attachment for structure of drug substance Table 85 Structure of Drug Substance Structural Formula : C18H20FN3O4 •½
The condensation product between the aromatic aldehydes and the aromatic ketones are 1,3-diphenylprop-2-en-1-ones, which are commonly known as chalcones. If any other types of aldehydes and ketones are used, the product is frequently known as α,β-unsaturated ketones. Chalcones and α,β-unsaturated ketones have been captivating, the medicinal,[1] synthetic,[2] and applied chemists[3] by virtue of their structural units (Figure 1) which have been gained many access to tailor the molecule suitably for wide range of applications in medicinal,[1] synthetic,[2] and applied chemistry.[3] The fluorine has the special topic of interest among the chemists as its introduction into the organic molecules leads to a dramatic changes in their physical and chemical properties.[4] The recent activities show a remarkable growth in fluorine chemistry as the chemists practiced to do polishing the organic molecules with fluorine to improve their properties, leading to widespread applications in medicinal,[4b,c,5] agrochemicals,[6]