Synthesis, Structure, and Bromination of 3-(Arylamino)-2-(4-arylthiazol-2-yl)acrylonitriles

Abstract

A series of previously undescribed 3-(arylamino)-2-(4-arylthiazol-2-yl)acrylonitriles were prepared by the Hantzsch reaction between 3-(arylamino)-2-cyanothioacrylamides and α-bromoketones. Bromination of the prepared 3-(arylamino)-2-(4-arylthiazol-2-yl)acrylonitriles proceeded regioselectively at the C5 position of, thiazole ring to form previously unknown 3-(arylamino)-2-(4-aryl-5-bromothiazol-2-yl)acrylonitriles in 42–85% yields. Structures of the new compounds were confirmed by 2D NMR (1H–13C, 1H–15N HSQC, 1H–13C, 1H–15N HMBC) and single crystal X-ray diffraction analysis.