Ciclização do lapachol induzida por sais de tálio III Cyclyzation of lapachol induced by thallium salts

Ciclização do lapachol induzida por sais de tálio III Cyclyzation of lapachol induced by thallium salts

<abstract language="eng">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...

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Bibliographic Details
Main Authors: Carlos Magno R. Ribeiro, Pablo P. de Souza, Letícia L. D. M. Ferreira, Lia A. Pinto, Leonardo S. de Almeida, Janaina G. de Jesus
Format: Article
Language:English
Published: Sociedade Brasileira de Química 2008-01-01
Series:Química Nova
Subjects:
lapachol
thallium salts
cyclization
Online Access:http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422008000400009
Description
Summary:<abstract language="eng">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.
ISSN:0100-4042
1678-7064

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