Old Drawback on Azlactone Formation Revealed by a Combination of Theoretical and Experimental Studies

New insights into the formation of azlactone heterocycles bearing different substituents are hereby presented. The sum of both kinetic and thermodynamic factors contributes for the formation of 2-alkyl or 2-aryl substituted azlactones, while the cyclization of 2-alcoxy azlactones is less favored. Th...

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Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 2018-11, Vol.29 (11), p.2213-2219
Main Authors: de Castro, Pedro, Batista, Gabriel, Pinheiro, Danielle, dos Santos, Hélio, Amarante, Giovanni
Format: Article
Language:English
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
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Summary:New insights into the formation of azlactone heterocycles bearing different substituents are hereby presented. The sum of both kinetic and thermodynamic factors contributes for the formation of 2-alkyl or 2-aryl substituted azlactones, while the cyclization of 2-alcoxy azlactones is less favored. These results are in perfect accordance with experimental observations obtained by infrared (IR) and electrospray ionization mass spectrometry (ESI(+)-MS) of the crude reaction mixture.
ISSN:0103-5053
1678-4790
1678-4790
DOI:10.21577/0103-5053.20180155