Eco-Friendly Synthesis and Insecticidal Activity of Some Fluorinated 2-(N-Arylamino)-4-Arylthiazoles

Abstract

A series of fluorinated 2-(N-arylamino)-4-arylthiazoles (3) was synthesized by the condensation of appropriate arylthioureas (2) with corresponding α-bromoacetophenones (1) by using “green chemistry” techniques, viz. mechanochemical mixing and microwave or ultrasonic irradiation. Compared with conventional procedures, the reaction can be carried out under milder conditions, requiring a shorter reaction time and giving higher yields following the green chemistry methodology. All the synthesized compounds were characterized on the basis of elemental analyses and spectral data (IR, 1H NMR, and mass spectrometry). Representative compounds were also evaluated for their insecticidal activity against Helicoverpa armigera, and some of them showed promising activity. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.