Alkylation of Oxazolones and Related Heterocycles through an SN1 Reaction

The alkylation of oxazolones through an SN1 reaction by using stabilized carbocations is reported. The reaction (catalyzed by Brønsted acids, such as TFA or thioureas) affords the final compounds in excellent yields. Reaction with other heterocycles has also been studied, rendering pyrazolone or oxi...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2011-04, Vol.2011 (11), p.2053-2056
Main Authors: Alba, Andrea-Nekane R., Calbet, Teresa, Font-Bardía, Mercé, Moyano, Albert, Rios, Ramon
Format: Article
Language:English
Subjects:
Alcohols
Brønsted acids
Chemistry
Exact sciences and technology
Green chemistry
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Lewis acids
Nucleophilic substitution
Organic chemistry
Preparations and properties
Àcids de Lewis
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Summary:The alkylation of oxazolones through an SN1 reaction by using stabilized carbocations is reported. The reaction (catalyzed by Brønsted 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. The Brønsted acid catalyzed alkylation of oxazolones, pyrazolones, and oxindolesaffords bulky derivatives in good yields.The reaction proceeds through an SN1 mechanism and involves stabilized carbocations.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201100046