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A facile microwave-assisted synthesis of oxazoles and diastereoselective oxazolines using aryl-aldehydes, p-toluenesulfonylmethyl isocyanide under controlled basic conditions
N. Mukku, P. Madivalappa Davanagere, , B. Maiti
Published in American Chemical Society
Volume: 5
Issue: 43
Pages: 28239 - 28248
In this study, a highly efficient two-component [3 + 2] cycloaddition reaction of substituted aryl aldehydes with 4-toluenesulfonylmethyl isocyanide (TosMIC) in the presence of 2 equiv of potassium phosphate as a base to 5-substituted oxazoles were established in a isopropanol medium under microwave irradiation. However, using 1 equiv of K3PO4 as a base resulted in the diastereoselective synthesis of 4,5-disubstituted oxazolines under identical reaction conditions. The foremost benefits of these protocols are the moderate-to-excellent yields with good functional group compatibility, simple experimental procedure, inexpensive readily available starting materials, nonchromatographic purification, and high bond-forming efficiency. The synthetic manipulation reported herein represents a cleaner route to the sustainable preparation of 5-substituted oxazoles and diastereoselective 4,5-disubstituted oxazolines derivatives. ©
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JournalData powered by TypesetACS Omega
PublisherData powered by TypesetAmerican Chemical Society