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 / A., Bolognese; G., Correale; M., Manfra; Lavecchia, Antonio; Novellino, Ettore; V., Barone. - In: TETRAHEDRON. - ISSN 0040-4020. - ELETTRONICO. - 60:(2004), pp. 8189-8197. [10.1016/j.tet.2004.06.098]
Reaction between Quinone and Thiazolidine. A Study on the Formation Mechanism of New Antiproliferative Quinolindiones
LAVECCHIA, ANTONIO;NOVELLINO, ETTORE;
2004
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.