The synthesis of 3‐hetaryl substituted coumarin derivatives [7‐hydroxy‐2H‐chromen‐2‐on and 9‐hydroxy‐2H‐benzo(f)chromen‐2‐on] containing a hydroxyl group by reacting 2,4‐dihydroxybenzaldehyde and 2,4‐dihydroxynaphtaldehydes with 2‐cyanomethylbenzothiazole, 2‐cyanomethylbenzimidazole, 1‐methyl‐2‐cyanomethylbenzimidazole and 2‐cyanomethyl‐4‐phenylthiazole is presented. The absorption and steady‐state fluorescence characteristics of the synthesised 3‐hetaryl substituted 7‐hydroxy‐2H‐chromen‐2‐on and 9‐hydroxy‐2H‐benzo(f)chromen‐2‐on in a solution of ethanol and at different pH values are studied to assess their possible application as fluorescent probes for use in molecular biology and medicine.
Eight novel 3‐hetaryl‐substituted 6‐ and 8‐hydroxybenzo[f]iminocoumarin compounds were synthesised by the reaction of 2,5‐dihydroxynaphthaldehydes or 2,7‐dihydroxynaphthaldehydes with 2‐cyanomethylbenzo‐thiazole, 2‐cyanomethylbenzoimidazole, 1‐methyl‐2‐cyanomethylbenzoimidazole and 2‐cyanomethyl‐4‐phenylthiazole. The iminocompounds obtained were hydrolysed with hydrochloric acid to the benzo[f]coumarins. Becaue of the high reactivity of the iminocoumarins, only mixtures which also contained the corresponding coumarin compounds were isolated. The absorption and steady‐state fluorescence characteristics of the benzo[f]coumarins (benzo[f]chromen‐2‐ones) synthesised were studied in ethanol and in toluene.
Two dihydroxynaphtaldehydes (2,5-dihydroxynaphtaldehyde and 2,7-dihydroxynaphtaldehyde) and 2,4dyhydroxybenzaldehyde were sulphonated. These intermediates were used in subsequent reactions with 2-cyanomethylbenzothiazole, 2-cyanomethylbenzoimidazole and 1-methyl-2-cyanomethylbenzoimidazole to synthesise sulphonated coumarin derivatives. The absorption and steady-state fluorescence characteristics of the prepared coumarins were studied in ethanol and in water.
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