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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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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The authors gratefully acknowledge the financial assistance by the VGST, Department of Information Technology, Biotechnology and Science & Technology, Government of Karnataka for the CESEM Award Grant No. 24 (2010-2011).

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Authors and Affiliations

  1. Department of Studies in Chemistry, Central College Campus, Bangalore University, Palace Road, Bengaluru, 560001, India

    Santhosh Govindaraju, Sumaiya Tabassum, Riyaz-ur-Rahaman Khan & Mohamed Afzal Pasha

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  1. Santhosh Govindaraju
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  2. Sumaiya Tabassum
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  3. Riyaz-ur-Rahaman Khan
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  4. Mohamed Afzal Pasha
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Corresponding author

Correspondence to Mohamed Afzal Pasha.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(11), 964–969

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Govindaraju, S., Tabassum, S., Khan, RuR. et al. 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. Chem Heterocycl Comp 52, 964–969 (2016). https://doi.org/10.1007/s10593-017-1994-z

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  • DOI: https://doi.org/10.1007/s10593-017-1994-z

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