Synthesis some of heterocyclic compounds derived from thymol

A series of some hydrazones derivatives (3-7) have been synthesized from the reaction of hydrazide (2) with substituted benzaldehyde. While oxazridine derivatives (8-12) were synthesized by oxidation with hydrazones derivatives (3-7) with m-chloro per benzoic acid, the of these compounds (8-12) with ammonium thiocyanate afforded compounds (1317). While the reaction of compound (2) with indole-2,3-dione afforded compound (18) while in reaction with mercaptoacetic acid gave Spiro indoline-2,3-thizolidine derivatives (19) when the compound allowed to react with conc., sulfuric acid and phosphoric pent oxide afford (20) and (21) respectively. Introduction Hydrazones derivatives have aroused considerable interest due to the used as intermediate to synthesis several heterocyclic compounds [1] . Oxaziridine compounds synthesized from oxidation ofimines derivatives using m-chloroperbenzoic acid [2] or through oxidation of hydrazones by per benzoic acid [3] .literature survey reveals that indole and thiazolidinone Derivatives are important for anti-inflammatory [4,5] , analgcsic [6] , Synthesis some of heterocyclic compounds derived from thymol 47 antibacterial [7] activities. Also several oxadiazol and thidazol derivatives have been found to be of interest with potential activities including antiinflammatory [8] insecticidal activities [9] . Experimental Melting points were measured on Electro thermal Melting Point Apparatus and are uncorrected. The IR spectra were recorded by using infrared spectrophotometer model Tensor 27 Brucker Co. Germany. Ethyl thymoxy acetate [1] This compound was prepared from the reaction of (0.06 mole, 9.0g) thymol, (0.06 mol, 8.28g) anhydrous potassium carbonate and (0.06 mole, 10.14g) bromoethylacetate following the method describe in the literature [10] , gave 96%, colorless oily product. Themoxy acetic acid hydrazide [2] This compound was prepared from the reaction of (0.05 mole, 12.89g) ester (1) and (0.25mole, 12.5g) hydrazine hydrate 99% as mentionedinthe literature [10] , yield 87%, m.p.(93-95 °C), lit.(93-95 °C). Hydrazones [11] (3-7) A mixture of hydrazide (2) (0.01 mole, 2.22g) and substituted aromatic aldehyde (0.01 mole) in 25ml ethanol, was heated under refluxed for 2 hours. After completion of reaction, it was cooled to room temperature. The precipitate was filtered and recrystalized from ethanol, to give the hydrazones (3-7). Some physical and spectral data indicated in Table (1, 4). Thymoxy methyl acetamido-2-aryl oxaziridine [12] (8-12) Hydrazones derivatives (3-7) (0.001mole) was dissolve in dry pyridine (4-6ml), followed by adding m-chloro per benzoic acid (0.002 mole, 0.34 g) (dissolved in 5 ml pyridine). The mixture was stirred for (12hours) at room temperature, ice-water was added and lefted over night, the precipitate was filtered and washed with hot water, dried. Recrysatllization from ethanol afforded the required compounds (8-12) .Some physical and spectral data indicated in Table (2, 5). 2-Thymoxy methyl acetamido-2-aryl thiazirdine [13] (13-17) Stirred a mixture of the appropriate oxazirdine derivative (8-12) (0.001 mol) in (15ml) dimethylforamide, ammonium thiocyant (0.002mole, 0.15g) (dissolved in 5ml DMF) was then added drops wise. The reaction mixture was stirred at room temperature for further 24 hrs, ice crushed ice was added to the reaction mixture and left for 4hrs, the