Synthesis of oxazolidin-2-ones derivatives was carried out starting from urea and ethanolamine reagents using microwave irradiation in a chemical paste medium.The synthesis of oxazolidin-2-ones has been performed by procedures that involve organic solvents 1-4 and expensive metallic catalysts. 5-8 These experimental conditions require long reaction times, 9-13 but the yields are less than satisfactory and many waste products are produced. [1][2][3][4][5] Despite these synthetic disadvantages, oxazolidinone derivatives are important heterocyclic compounds that are useful as inhibitors of animal cell motility and growth, 14 possible sphingomyelinase inhibitors, 15 inhibitors of the cytochrome P-450 enzyme aromatase, 2,16 drugs with antibacterial activity against methicillin-resistant Staphylococcus aureus and Bacillus anthracis, 17,18 and fungicidal pest control agents. 19 We have previously utilized microwave-chemical activation for the synthesis of new organic compounds. 20-23 Therefore, we realized a procedure for the synthesis of oxazolidin-2-ones 3 from the condensation of ethanolamine derivatives 1 and urea (2) (Scheme 1).
Scheme 1The synthesis takes place in a paste-like chemical medium. This medium resulted from the addition of a small amount of polar solvent, nitromethane, which does not react with the reagents. 22,23 Nitromethane molecules absorb the microwaves and generate hot spots in the reaction medium, the hot spots then act like catalytic centers. 20,21 As a result the oxazolidin-2-ones 3 were easily obtained with short reaction times and high yields. Moreover, simple experimental apparatus, easy product separation, and high purity of the compounds are important advantages of this method.Ethanolamines and urea are commercially available substances. The synthesized products were identified by TLC (silica gel, EtOH), elemental analysis, and their IR spectra. Melting points were measured on a Böetius melting point apparatus. The IR spectra were recorded as KBr pellets with using a Perkin-Elmer 1600 spectrophotometer. Elemental analyses were carried out with a Carlo Erba model 1106 apparatus. An Optiquick Y71 microwave oven operating at 650 W was employed.
Oxazolidin-2-ones 3; General ProcedureThe ethanolamine derivative 1 (2 mmol) and urea (2, 2 mmol) were mixed in a 25 mL Pyrex beaker. A few drops of MeNO 2 were added and the resulting paste was irradiated in a microwave oven (l = 12.2 cm) for the required time. The resulting residue was purified by recrystallization (CHCl 3 -EtOH) to give the oxazolidin-2-ones 3 as colorless crystals (Tables 1 and 2).
References(1) Madesclaire, M.; Coudert, P.; Zaitsev, V. P.; Zaitseva, J. V. Chem. Heterocycl. Compd. (Engl. Transl.) 2006, 42, 506. (2) Ahmed, S.; Adat, S.; Murrells, A.; Owen, C. P.; Amanuel, Y.