An efficient synthesis of novel coumarinyldihydropyrimidin-2-thiones via coumarinylenones

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• Typical method for the synthesis of (E, Z) methyl 2-[(7′,8′-dimethoxycoumarin-4′-yl)methylene]-3-oxobutanoate (2a). To a mixture of 4-formylcoumarins 1a (1 mmol) and β-ketoester 5a (1.12 mmol) was dissolved in acetonitrile in a round-bottom flask, AlCl3 (0.1 mmol) was added, and reaction mixture was refluxed at 85 °C for 5–7 h. After completion of the reaction (as monitored by TLC examination), the reaction mixture was cooled down and then ice-cold water (50 mL) was added to the reaction mixture. Then, the solid separated out was filtered through sintered funnel and dried to get crude product which was further purified by column chromatography using 1% MeOH in chloroform as eluent. After column chromatography, the compound 2a was obtained as a mixture of E- and Z-isomers in the ratio of 2:3 as determined by integrating coumarin C-3′ proton in 1H-NMR spectra.
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• Typical method for the synthesis of methyl 4-(7′,8′-dimethoxycoumarin-4′-yl)-2-[(4-methoxybenzyl)thio]-6-methyl-1,4-dihydropyrimidine-5-carboxylate (7a). To a mixture of methyl 2-[(7′,8′-dimethoxycoumarin-4′-yl)methylene]-3-oxobutanoate 2a (1 mmol) and 2-(4-methoxybenzyl)isothiourea hydrochloride 6 (2 mmol) in THF (10 ml) in a 25 mL round-bottom flask, added NaOAc (2 mmol) and reaction mixture was refluxed on oil bath for 4 h. After completion of reaction (as monitored by TLC), the solvent was removed, and ice-cold water (20 mL) was added to the residue. The solid obtained was filtered through sintered funnel and dissolved in ethyl acetate (50 mL) which further dried over sodium sulphate, filtered and the organic layer was evaporated to get crude product 7a which was further purified by column chromatography using 1% MeOH in chloroform as eluent.
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• Typical method for the synthesis of methyl 4-(7′,8′-dimethoxycoumarin-4′-yl)-2-thioxo-6-methyl-3,4-dihydropyrimidine-5-carboxylate (3a). To a solution of methyl 4-(7′,8′-dimethoxycoumarin-4′-yl)-2-[(4-methoxybenzyl)thio]-6-methyl-1,4-dihydro-pyrimidine-5-carboxylate 7a (0.667 mmol) in DCM, added a mixture of TFA/EtSH (2:1) and reaction mixture was stirred at room temperature under nitrogen atmosphere for 2 h. After completion of reaction (as monitored by TLC), solvent was evaporated and crude reaction mass of compound 3a was purified by column chromatography using 2% MeOH in chloroform as eluent.
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