A Mild and Convenient Synthesis of 4-Tosyl-4,5-dihydrooxazoles

Xavier      Companyo; Albert      Moyano; Ramon      Rios

doi:10.2174/157017809788489855

Abstract

A facile and mild synthesis of 4-tosyl-4,5-dihydrooxazoles is described. The reaction between tosyl methyl isocyanide (TosMIC) and cinnamic or aromatic aldehydes is catalyzed by triethylamine, affording trans-5-styryl- or 5-aryl-4- tosyl-4,5-dihydrooxazoles in quantitative yields without further purification. The mild reaction conditions allowed for the first time the use of cinnamaldehyde derivatives with excellent results.

Keywords: TosMIC, Catalytic reaction, α,β-Unsaturated aldehydes, Oxazolines, 4,5-Dihydrooxazoles

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Letters in Organic Chemistry

Title: A Mild and Convenient Synthesis of 4-Tosyl-4,5-dihydrooxazoles

Volume: 6 Issue: 4

Author(s): Xavier Companyo, Albert Moyano and Ramon Rios

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Keywords: TosMIC, Catalytic reaction, α,β-Unsaturated aldehydes, Oxazolines, 4,5-Dihydrooxazoles

Abstract: A facile and mild synthesis of 4-tosyl-4,5-dihydrooxazoles is described. The reaction between tosyl methyl isocyanide (TosMIC) and cinnamic or aromatic aldehydes is catalyzed by triethylamine, affording trans-5-styryl- or 5-aryl-4- tosyl-4,5-dihydrooxazoles in quantitative yields without further purification. The mild reaction conditions allowed for the first time the use of cinnamaldehyde derivatives with excellent results.

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Companyo Xavier, Moyano Albert and Rios Ramon, A Mild and Convenient Synthesis of 4-Tosyl-4,5-dihydrooxazoles, Letters in Organic Chemistry 2009; 6 (4) . https://dx.doi.org/10.2174/157017809788489855