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A Facile Microwave-Assisted Synthesis of Oxazoles and Diastereoselective Oxazolines Using Aryl-Aldehydes, p-Toluenesulfonylmethyl Isocyanide under Controlled Basic Conditions.


ABSTRACT: 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.

SUBMITTER: Mukku N 

PROVIDER: S-EPMC7643254 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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A Facile Microwave-Assisted Synthesis of Oxazoles and Diastereoselective Oxazolines Using Aryl-Aldehydes, <i>p</i>-Toluenesulfonylmethyl Isocyanide under Controlled Basic Conditions.

Mukku Narasimharao N   Madivalappa Davanagere Prabhakara P   Chanda Kaushik K   Maiti Barnali B  

ACS omega 20201020 43


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 K<sub>3</sub>PO<sub>4</sub> as a base resulted in the diastereoselective synthesis of 4,5-disubstituted oxazolines under identical reaction conditions. The fore  ...[more]

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