Microwave assisted one pot synthesis of 7-substituted 2-(2-oxo-2H-chromen-3-yl)acetic acids as precursors of new anti-tumour compounds

被引:0
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作者
Silvia Kováčová
Lucia Kováčiková
Margita Lácová
Andrej Boháč
Marta Sališová
机构
[1] Comenius University,Department of Organic Chemistry, Faculty of Natural Sciences
来源
Chemical Papers | 2010年 / 64卷
关键词
microwave; coumarine; Perkin condensation; Perkin lactonisation; anti-cancer compounds; fluorescence;
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学科分类号
摘要
Perkin condensation with subsequent intramolecular lactonisation as one pot syntheses of 2-(2-oxo-2H-chromen-3-yl)acetic acids VIIa-Xa has been studied. The required acids VIIa-Xa were prepared as precursors of recently discovered compounds possessing antineoplastic activities. Syntheses of VIIa-Xa were carried out using para substituted 2-hydroxybenzaldehydes II-VI, succinic acid anhydride, sodium succinate under thermal or microwave conditions. Significant shortening of the reaction time under microwave irradiation was observed (18–50 min instead of 1.5–5 h of heating). Microwave assisted reactions proceeded more smoothly to give higher yield of the required products VIIa-Xa (31–61 %) compared to those under classical thermal conditions e.g. 21.8 % for IXa (Hurenkamp et al., 2007). Seven reaction by-products were isolated and determined as 2H,2′H-3,3′-bichromene-2,2′-diones VIIb-Xb and (E)-3-(2-hydroxystyryl)-2H-chromen-2-ones VIIc-IXc.
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页码:806 / 811
页数:5
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