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

Xavier Companyó; Albert Moyano; Ramon Rios

doi:10.2174/157017809788489855

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

Xavier Companyó, Albert Moyano, Ramon Rios

Chemistry

Universitat de Barcelona

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

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.

Original language	British English
Pages (from-to)	293-296
Number of pages	4
Journal	Letters in Organic Chemistry
Volume	6
Issue number	4
DOIs	https://doi.org/10.2174/157017809788489855
State	Published - Jun 2009

Keywords

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

Access to Document

10.2174/157017809788489855

Cite this

@article{996e789037204591bb98a1f78a496ccf,

title = "A Mild and convenient synthesis of 4-tosyl-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.",

keywords = "α,β-Unsaturated aldehydes, 4,5-Dihydrooxazoles, Catalytic reaction, Oxazolines, TosMIC",

author = "Xavier Company{\'o} and Albert Moyano and Ramon Rios",

year = "2009",

month = jun,

doi = "10.2174/157017809788489855",

language = "British English",

volume = "6",

pages = "293--296",

journal = "Letters in Organic Chemistry",

issn = "1570-1786",

publisher = "Bentham Science Publishers B.V.",

number = "4",

}

TY - JOUR

T1 - A Mild and convenient synthesis of 4-tosyl-4,5-dihydrooxazoles

AU - Companyó, Xavier

AU - Moyano, Albert

AU - Rios, Ramon

PY - 2009/6

Y1 - 2009/6

N2 - 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.

AB - 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.

KW - α,β-Unsaturated aldehydes

KW - 4,5-Dihydrooxazoles

KW - Catalytic reaction

KW - Oxazolines

KW - TosMIC

UR - http://www.scopus.com/inward/record.url?scp=69549126393&partnerID=8YFLogxK

U2 - 10.2174/157017809788489855

DO - 10.2174/157017809788489855

M3 - Article

AN - SCOPUS:69549126393

SN - 1570-1786

VL - 6

SP - 293

EP - 296

JO - Letters in Organic Chemistry

JF - Letters in Organic Chemistry

IS - 4

ER -

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this