Recent progress of synthesis of new arylazoazoles based on bis(carbothioamides)

Abstract

In this study, new bisthiazoles were efficiently synthesized from the reaction of hydrazine-1,2-bis(carbothioamide) with N-aryl-2-oxopropanehydrazonoyl chlorides or N-aryl C-ethoxycarbonyl methanehydrazonoyl chlorides. The formation of the final compounds starts by nucleophilic attack of thiolates to give S-alkylated intermediate, which in situ undergoes nucleophilic addition and intramolecular cyclization to give the final products as described in the synthetic schemes. The inexpensive and simple reaction conditions, commercial availability of the reagent, good yields and excellent purities of the products make this method valuable from a preparative point of view. Furthermore, the antibacterial activities values of the new compounds were evaluated against Gram-positive and Gram-negative microorganisms. The final products were identified and characterized by elemental analysis, Fourier transforms infrared spectroscopy (FT-IR), mass spectrometry (MS), and nuclear magnetic resonance (NMR).