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

• Published in: Chemical papers 2010, Vol.64 (6), p.806-811
• Main Authors: Kováčová, Silvia, Kováčiková, Lucia, Lácová, Margita, Boháč, Andrej, Sališová, Marta
• Format: Article
• Language: English
• Subjects: anti-cancer compounds; Biochemistry; Biotechnology; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; coumarine; fluorescence; Industrial Chemistry/Chemical Engineering; Materials Science; Medicinal Chemistry; microwave; Original Paper; Perkin condensation; Perkin lactonisation
• ISSN: 0366-6352; 1336-9075; 1336-9075
• DOI: 10.2478/s11696-010-0059-x

Perkin condensation with subsequent intramolecular lactonisation as one pot syntheses of 2-(2-oxo-2 H -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 2 H ,2′ H -3,3′-bichromene-2,2′-diones VIIb-Xb and ( E )-3-(2-hydroxystyryl)-2 H -chromen-2-ones VIIc-IXc .