Regioselective three-component synthesis and theoretical calculations of new alkane-linked bis(thiazol-2(3H)-imine) hybrids: a DFT-based FMO and local reactivity indices

Abstract

A three-component approach was conducted to adeptly prepare a new series of (Z)-bis(N-phenylthiazol-2(3H)-imines. The newly synthesized compounds were prepared by refluxing a ternary mixture of phenyl isothiocyanate, the suitable α-bromoketones, and alkane-linked diamines in ethanol. Reaction conditions were optimized by comparing the yield of the final product under various bases, solvents, temperatures, and base-to-starting-materials molar ratios. The intended hybrids were produced with 85–96% yields while using ethanol at 80 °C for 3–5 h in the presence of anhydrous sodium acetate. The ascribed configuration of new products as well as the regioselectivity of the one-pot reaction were confirmed using both spectral data (1D and 2D NMR) and DFT-calculation techniques. Graphical abstract