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CATALYST-FREE GREEN SYNTHESIS OF NOVEL 2-AMINO-4-ARYL-3-(4-FLUOROPHENYL)-4,6,7,8-TETRAHYDROQUINOLIN-5(1H)-ONES VIA A ONE-POT FOUR-COMPONENT REACTION UNDER ULTRASONIC CONDITION

Santhosh Govindaraju, Sumaiya Tabassum, Riyaz Ur-Rahaman Khan, Mohamed Afzal Pasha
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Abstract


The investigation presents a straightforward synthesis of fourteen novel 2-amino-4-aryl-3-(4-fluorophenyl)-4,6,7,8-tetrahydroquinolin-5(1H)-one derivatives via a catalyst-free one-pot four-component cyclocondensation reaction of dimedone, various substituted benzaldehydes, 4-fluorophenylacetonitrile, and ammonium acetate in water under the influence of ultrasound. In comparison with the literature methods, our approach is more effective and offers several advantages, such as safe handling, excellent yields, shorter reaction time, and a simple workup procedure. All the synthesized derivatives were obtained in 87–97% yields and were characterized by IR, 1H, 13C NMR, and ESI mass spectra and elemental analysis.


Keywords


4,6,7,8-tetrahydroquinolin-5(1H)-ones; aqueous medium; catalyst-free reaction; one-pot four-component reaction; ultrasonic irradiation

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