Ciclização do lapachol induzida por sais de tálio III

Ciclização do lapachol induzida por sais de tálio III

This work describes the cyclization of lapachol (1) induced by thallium triacetate (TTA) and thallium trinitrate (TTN) in several solvents using magnetic stirring and under microwave irradiation. alpha-Xyloidone (2) - dehydro-alpha-lapachone - was obtained as the main product in these reactions in 20 75% yield. However, rhinacanthin-A (4) was isolated as main product in a 40% yield, using TTA and acetic anhydride:water (1:1) as solvent, and dehydro-iso-alpha-lapachone (3) in 21% yield, using TTA and dichloromethane as solvent. The reaction time decreased drastically under microwave conditions, but the yields of these reactions were not the expected.

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Main Authors: Ribeiro,Carlos Magno R., Souza,Pablo P. de, Ferreira,Letícia L. D. M., Pinto,Lia A., Almeida,Leonardo S. de, Jesus,Janaina G. de
Format: Digital revista
Language:Portuguese
Published: Sociedade Brasileira de Química 2008
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422008000400009
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spelling oai:scielo:S0100-404220080004000092008-06-16Ciclização do lapachol induzida por sais de tálio IIIRibeiro,Carlos Magno R.Souza,Pablo P. deFerreira,Letícia L. D. M.Pinto,Lia A.Almeida,Leonardo S. deJesus,Janaina G. de lapachol thallium salts cyclization This work describes the cyclization of lapachol (1) induced by thallium triacetate (TTA) and thallium trinitrate (TTN) in several solvents using magnetic stirring and under microwave irradiation. alpha-Xyloidone (2) - dehydro-alpha-lapachone - was obtained as the main product in these reactions in 20 75% yield. However, rhinacanthin-A (4) was isolated as main product in a 40% yield, using TTA and acetic anhydride:water (1:1) as solvent, and dehydro-iso-alpha-lapachone (3) in 21% yield, using TTA and dichloromethane as solvent. The reaction time decreased drastically under microwave conditions, but the yields of these reactions were not the expected.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaQuímica Nova v.31 n.4 20082008-01-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422008000400009pt10.1590/S0100-40422008000400009
institution SCIELO
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country Brasil
countrycode BR
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databasecode rev-scielo-br
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region America del Sur
libraryname SciELO
language Portuguese
format Digital
author Ribeiro,Carlos Magno R.
Souza,Pablo P. de
Ferreira,Letícia L. D. M.
Pinto,Lia A.
Almeida,Leonardo S. de
Jesus,Janaina G. de
spellingShingle Ribeiro,Carlos Magno R.
Souza,Pablo P. de
Ferreira,Letícia L. D. M.
Pinto,Lia A.
Almeida,Leonardo S. de
Jesus,Janaina G. de
Ciclização do lapachol induzida por sais de tálio III
author_facet Ribeiro,Carlos Magno R.
Souza,Pablo P. de
Ferreira,Letícia L. D. M.
Pinto,Lia A.
Almeida,Leonardo S. de
Jesus,Janaina G. de
author_sort Ribeiro,Carlos Magno R.
title Ciclização do lapachol induzida por sais de tálio III
title_short Ciclização do lapachol induzida por sais de tálio III
title_full Ciclização do lapachol induzida por sais de tálio III
title_fullStr Ciclização do lapachol induzida por sais de tálio III
title_full_unstemmed Ciclização do lapachol induzida por sais de tálio III
title_sort ciclização do lapachol induzida por sais de tálio iii
description This work describes the cyclization of lapachol (1) induced by thallium triacetate (TTA) and thallium trinitrate (TTN) in several solvents using magnetic stirring and under microwave irradiation. alpha-Xyloidone (2) - dehydro-alpha-lapachone - was obtained as the main product in these reactions in 20 75% yield. However, rhinacanthin-A (4) was isolated as main product in a 40% yield, using TTA and acetic anhydride:water (1:1) as solvent, and dehydro-iso-alpha-lapachone (3) in 21% yield, using TTA and dichloromethane as solvent. The reaction time decreased drastically under microwave conditions, but the yields of these reactions were not the expected.
publisher Sociedade Brasileira de Química
publishDate 2008
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422008000400009
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AT pintoliaa ciclizacaodolapacholinduzidaporsaisdetalioiii
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