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

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 52; no. 11; pp. 964 - 969
• Main Authors: Govindaraju, Santhosh, Tabassum, Sumaiya, Khan, Riyaz-ur-Rahaman, Pasha, Mohamed Afzal
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.11.2016; Springer Nature; Springer Nature B.V
• Subjects: Ammonium acetate; Aromatic compounds; Catalysts; Chemical analysis; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry, Organic; Mass spectra; NMR; Nuclear magnetic resonance; Organic Chemistry; Pharmacy; Physical Sciences; Reaction time; Science & Technology; ones; catalyst-free reaction; one-pot four-component reaction; ultrasonic irradiation; aqueous medium; 4,6,7,8-tetrahydroquinolin-5; SOLVENT-FREE CONDITIONS; ISOCYANIDES; BIGINELLI REACTION; LIBRARIES; MULTICOMPONENT REACTIONS; IRRADIATION; CHEMISTRY; GENERATION; 4,6,7,8-tetrahydroquinolin-5(1H)-ones; EFFICIENT; CHLORIDE
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-017-1994-z

The investigation presents a straightforward synthesis of fourteen novel 2-amino-4-aryl-3-(4-fluorophenyl)-4,6,7,8-tetrahydroquinolin-5(1 H )-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, 1 H, 13 C NMR, and ESI mass spectra and elemental analysis.