One-pot Synthesis and Characterization of Highly Functionalized Thiazoles

• Main Authors: Hamid Beyzaei, Adel Beygi, Reza Aryan
• Format: Article
• Language: English
• Published: Iranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECR 2016-12-01
• Series: Iranian Journal of Chemistry & Chemical Engineering
• Subjects: one-pot synthesis; thiazole; cyclocondensation; hydrazine; hydrazide
• Online Access: http://www.ijcce.ac.ir/article_23554_efe2f2723e2de8a9d2237b5a1181ea3f.pdf

A facile and efficient one-pot three-step process for the synthesis of 5-acetyl-2-imino-4-methylthiazoles via the cyclocondensation of 3-thiocyanatoacetylacetone with various hydrazine or hydrazide derivatives in EtOH has been developed. 3-Thiocyanatoacetylacetone itself has been synthesized as the intermediate from substitution reaction of thiocyanate with 3-chloroacetylacetone. Better results were obtained by three-step procedures vs one-step reaction. The proposed method does not require techniques such as extraction and chromatography. Surprisingly, 3,5-dimethyl-4-thiocyanato-1H-pyrazoles were not produced in this reaction, it was proved based on the existence of the acetyl group in the products. The molecular structures of newly synthesized compounds were elucidated on the basis of elemental analysis and spectral data.