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Alkylation of oxazolones and related heterocycles through an S(N)1 reaction

Alkylation of oxazolones and related heterocycles through an S(N)1 reaction
Alkylation of oxazolones and related heterocycles through an S(N)1 reaction
The alkylation of oxazolones through an S(N)1 reaction by using stabilized carbocations is reported. The reaction (catalyzed by Bronsted acids, such as TFA or thioureas) affords the final compounds in excellent yields. Reaction with other heterocycles has also been studied, rendering pyrazolone or oxindole derivatives in good yields.
alcohols, lewis acids, brønsted acids, nucleophilic substitution, green chemistry
1434-193X
2053-2056
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Calbet, Teresa
f09dc31e-22d8-4f56-9a48-6b71cdcccd27
Font-Bardía, Mercé
41a15fd1-a12e-4bfc-9d86-3e209684ed2b
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Calbet, Teresa
f09dc31e-22d8-4f56-9a48-6b71cdcccd27
Font-Bardía, Mercé
41a15fd1-a12e-4bfc-9d86-3e209684ed2b
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Alba, Andrea-Nekane R., Calbet, Teresa, Font-Bardía, Mercé, Moyano, Albert and Rios, Ramon (2011) Alkylation of oxazolones and related heterocycles through an S(N)1 reaction. European Journal of Organic Chemistry, 2011 (11), 2053-2056. (doi:10.1002/ejoc.201100046).

Record type: Article

Abstract

The alkylation of oxazolones through an S(N)1 reaction by using stabilized carbocations is reported. The reaction (catalyzed by Bronsted acids, such as TFA or thioureas) affords the final compounds in excellent yields. Reaction with other heterocycles has also been studied, rendering pyrazolone or oxindole derivatives in good yields.

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More information

e-pub ahead of print date: 23 February 2011
Published date: April 2011
Keywords: alcohols, lewis acids, brønsted acids, nucleophilic substitution, green chemistry
Organisations: Chemistry

Identifiers

Local EPrints ID: 344064
URI: https://eprints.soton.ac.uk/id/eprint/344064
ISSN: 1434-193X
PURE UUID: 6036f760-b814-4224-9dde-f5a43a61147c
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 07 Jul 2016 13:45
Last modified: 20 Jul 2019 00:42

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Contributors

Author: Andrea-Nekane R. Alba
Author: Teresa Calbet
Author: Mercé Font-Bardía
Author: Albert Moyano
Author: Ramon Rios ORCID iD

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