Study on condensation of N-aryl thioureas with 3-bromo-acetylacetone: Synthesis of aminothiazoles and iminodihydrothiazoles, and their in vitro antiproliferative activity on human cervical cancer cells

✍ Scribed by Hai-Bo Shi; Shi-Jie Zhang; Yan-Fang Lin; Wei-Xiao Hu; Chao-Ming Cai

• Book ID: 102343231
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2011
• Tongue: English
• Weight: 290 KB
• Volume: 48
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.602

✦ Synopsis

Abstract

The condensation of N‐aryl thioureas with 3‐bromo‐acetylacetone in neutral solvent acetone not only led to 5‐acetyl‐4‐methyl‐2‐(substituted anilino) thiazoles 3 but also 2‐imino‐3‐(substituted phenyl)‐4‐methyl‐5‐acetyl‐2,3‐dihydrothiazoles 4. Further study found that different reaction solvents displayed an important role toward the ratio of aminothiazoles 3 and iminodihydrothiazoles 4, and the reaction scope was extended. A plausible mechanism involving solvent effect and in situ hydrobromic acid catalyzation was proposed. Some selected isomers exhibited moderate in vitro antiproliferative activity on human cervical cancer cell lines (Hela, Siha). J. Heterocyclic Chem., (2011).