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

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. 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.

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Main Authors: Castro,Pedro P. de, Batista,Gabriel M. F., Pinheiro,Danielle L. J., Santos,Hélio F. dos, Amarante,Giovanni W.
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2018
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018001102213
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spelling oai:scielo:S0103-505320180011022132018-10-15Old Drawback on Azlactone Formation Revealed by a Combination of Theoretical and Experimental StudiesCastro,Pedro P. deBatista,Gabriel M. F.Pinheiro,Danielle L. J.Santos,Hélio F. dosAmarante,Giovanni W. azlactone oxazolone DFT 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.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.29 n.11 20182018-11-01info:eu-repo/semantics/othertext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018001102213en10.21577/0103-5053.20180155
institution SCIELO
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country Brasil
countrycode BR
component Revista
access En linea
databasecode rev-scielo-br
tag revista
region America del Sur
libraryname SciELO
language English
format Digital
author Castro,Pedro P. de
Batista,Gabriel M. F.
Pinheiro,Danielle L. J.
Santos,Hélio F. dos
Amarante,Giovanni W.
spellingShingle Castro,Pedro P. de
Batista,Gabriel M. F.
Pinheiro,Danielle L. J.
Santos,Hélio F. dos
Amarante,Giovanni W.
Old Drawback on Azlactone Formation Revealed by a Combination of Theoretical and Experimental Studies
author_facet Castro,Pedro P. de
Batista,Gabriel M. F.
Pinheiro,Danielle L. J.
Santos,Hélio F. dos
Amarante,Giovanni W.
author_sort Castro,Pedro P. de
title Old Drawback on Azlactone Formation Revealed by a Combination of Theoretical and Experimental Studies
title_short Old Drawback on Azlactone Formation Revealed by a Combination of Theoretical and Experimental Studies
title_full Old Drawback on Azlactone Formation Revealed by a Combination of Theoretical and Experimental Studies
title_fullStr Old Drawback on Azlactone Formation Revealed by a Combination of Theoretical and Experimental Studies
title_full_unstemmed Old Drawback on Azlactone Formation Revealed by a Combination of Theoretical and Experimental Studies
title_sort old drawback on azlactone formation revealed by a combination of theoretical and experimental studies
description 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.
publisher Sociedade Brasileira de Química
publishDate 2018
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018001102213
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AT pinheirodaniellelj olddrawbackonazlactoneformationrevealedbyacombinationoftheoreticalandexperimentalstudies
AT santosheliofdos olddrawbackonazlactoneformationrevealedbyacombinationoftheoreticalandexperimentalstudies
AT amarantegiovanniw olddrawbackonazlactoneformationrevealedbyacombinationoftheoreticalandexperimentalstudies
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