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A mild and convenient synthesis of 4-tosyl-4,5-dihydrooxazoles

A mild and convenient synthesis of 4-tosyl-4,5-dihydrooxazoles
A mild and convenient synthesis of 4-tosyl-4,5-dihydrooxazoles
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.
TosMIC, catalytic reaction, ?, ?-unsaturated aldehydes, oxazolines, 4, 5-dihydrooxazoles
1570-1786
293-296
Companyo, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Companyo, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Companyo, Xavier, Moyano, Albert and Rios, Ramon (2009) A mild and convenient synthesis of 4-tosyl-4,5-dihydrooxazoles. Letters in Organic Chemistry, 6 (4), 293-296.

Record type: Article

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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More information

Published date: 1 June 2009
Keywords: TosMIC, catalytic reaction, ?, ?-unsaturated aldehydes, oxazolines, 4, 5-dihydrooxazoles
Organisations: Chemistry

Identifiers

Local EPrints ID: 347723
URI: http://eprints.soton.ac.uk/id/eprint/347723
ISSN: 1570-1786
PURE UUID: 5d0656c8-b66d-480b-8374-5e72d1326ce3
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 29 Jan 2013 13:01
Last modified: 07 Oct 2020 02:01

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