Reaction between quinolinquinone and thiazolidine in basic medium was investigated. 2-Arylthiazolidine-4-carboxylic acid ethyl esters undergo two different cleavages in basic medium, yielding the 1-aryl-2-azadiene and a thiolic species. In the presence of quinolinquinone, the isomeric 1-aryl-3-ethoxycarbonyl-pyridoisoquinolin-5,10-diones and 3-amino-3-ethoxycarbonyl-dihydrothienoquinolin- 4,9-diones are formed by a hetero-Diels–Alder reaction and 1,4-Michael addition reaction, respectively. A mechanism for the formation of the reaction products is presented.
Reaction between quinone and thiazolidine. A study on the formation mechanism of new antiproliferative quinolindiones
MANFRA, MICHELE;
2004-01-01
Abstract
Reaction between quinolinquinone and thiazolidine in basic medium was investigated. 2-Arylthiazolidine-4-carboxylic acid ethyl esters undergo two different cleavages in basic medium, yielding the 1-aryl-2-azadiene and a thiolic species. In the presence of quinolinquinone, the isomeric 1-aryl-3-ethoxycarbonyl-pyridoisoquinolin-5,10-diones and 3-amino-3-ethoxycarbonyl-dihydrothienoquinolin- 4,9-diones are formed by a hetero-Diels–Alder reaction and 1,4-Michael addition reaction, respectively. A mechanism for the formation of the reaction products is presented.File in questo prodotto:
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2004 Tetrahedron 60 (2004) 8189-8197.pdf
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