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Reaction between quinone and thiazolidine. A study on the formation mechanism of new antiproliferative quinolindiones |
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| Authors: | Adele Bolognese Gaetano Correale Antonio Lavecchia Vincenzo Barone |
| Affiliation: | a Dipartimento di Chimica Organica e Biochimica, Università di Napoli “Federico II”, Via Cynthia 6, Monte Sant'Angelo, I-80126 Napoli, Italy b Dipartimento di Chimica Farmaceutica e Tossicologica, Università di Napoli “Federico II”, Via D. Montesano 49, 80131 Napoli, Italy c Dipartimento di Chimica, Università di Napoli “Federico II”, Via Cynthia 6, Monte Sant'Angelo, I-80126 Napoli, Italy |
| 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. |
| Keywords: | Quinone Thiazolidine Azadiene |
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